chore: release v0.9.0 (#278)

Co-authored-by: github-actions[bot] <41898282+github-actions[bot]@users.noreply.github.com>

.claude/commands/triage-issues.md

@@ -0,0 +1,257 @@
+---
+description: Triage open GitHub issues — split into bugs vs features, rank by severity/opportunity, and flag under-specified issues
+disable-model-invocation: true
+allowed-tools: Bash(gh issue list:*), Bash(gh issue view:*), Bash(gh api:*), Bash(git log:*), Read, Grep, Glob, Task
+argument-hint: "[--label=<filter>] [--milestone=<filter>]"
+---
+
+# Issue Triage
+
+You are triaging all open issues on this repository. Your job is to split them into **bugs** and **feature requests**, rank each group, assess how well-specified each issue is, and produce an actionable triage report.
+
+## Step 1: Fetch all open issues
+
+Fetch every open issue with metadata:
+
+```
+gh issue list --state open --limit 200 --json number,title,author,labels,assignees,createdAt,updatedAt,body,commentsCount,reactionGroups,milestone
+```
+
+If `$ARGUMENTS` contains `--label=<X>`, append `--label '<X>'` to the command. If it contains `--milestone=<X>`, append `--milestone '<X>'` to the command.
+
+Also fetch recently closed issues (last 14 days) to detect duplicates and already-resolved work:
+
+```
+gh issue list --state closed --search "closed:>=$(date -v-14d +%Y-%m-%d)" --limit 100 --json number,title,body,labels,closedAt
+```
+
+**Exclude pull requests** — `gh issue list` may include PRs. Fetch open PR numbers to filter them out:
+
+```
+gh pr list --state open --json number --jq '.[].number'
+```
+
+Remove any issue whose number appears in this list.
+
+## Step 2: Classify each issue as Bug or Feature
+
+Read each issue's title, body, and labels to classify it into one of these categories:
+
+### Bugs
+Issues that describe **broken existing behavior** — something that worked or should work but doesn't. Signals:
+- Labels: `bug`, `defect`, `regression`, `crash`, `error`
+- Title/body keywords: "broken", "fails", "crash", "panic", "error", "regression", "doesn't work", "unexpected behavior"
+- Includes reproduction steps or error output
+- References existing functionality not working as documented
+
+### Feature Requests
+Issues that describe **new or enhanced behavior** — something that doesn't exist yet. Signals:
+- Labels: `enhancement`, `feature`, `feature-request`, `improvement`, `proposal`
+- Title/body keywords: "add", "support", "implement", "would be nice", "proposal", "RFC", "new"
+- Describes a capability the project doesn't have
+- Proposes a design or API change
+
+### Ambiguous
+If an issue doesn't clearly fit either category (e.g., "improve X performance" could be a bug or a feature), classify it as **Ambiguous** and note why.
+
+## Step 3: Rate issue detail level
+
+For each issue, assess how well-specified it is on a 3-tier scale:
+
+| Detail Level | Criteria |
+|-------------|----------|
+| **Well-specified** | Has clear description of what/why, reproduction steps (bugs) or user story (features), acceptance criteria or expected behavior, and enough context to start working immediately |
+| **Adequate** | Describes the problem or request clearly, but missing some detail — no repro steps, vague acceptance criteria, or unclear scope. Needs 1-2 clarifying questions before work can start |
+| **Under-specified** | Vague title-only or single-sentence body, no context on why it matters, no clear definition of done. Needs significant discussion before it's actionable |
+
+Indicators of good specification:
+- Code snippets, error logs, or screenshots
+- Steps to reproduce (bugs)
+- Proposed API/behavior (features)
+- Links to related issues or discussions
+- Clear "done when" criteria
+
+## Step 4: Rank bugs by severity
+
+Score each bug on these dimensions and compute an overall severity rank:
+
+### Impact (1-4)
+| Score | Level | Description |
+|-------|-------|-------------|
+| 4 | **Critical** | Data loss, security vulnerability, complete feature broken, crash in common path |
+| 3 | **High** | Major feature degraded, workaround exists but painful, affects many users |
+| 2 | **Medium** | Minor feature broken, easy workaround, affects subset of users |
+| 1 | **Low** | Cosmetic, edge case, documentation error, minor inconvenience |
+
+### Urgency (1-3)
+| Score | Level | Description |
+|-------|-------|-------------|
+| 3 | **Urgent** | Security issue, regression in recent release, blocking other work |
+| 2 | **Normal** | Should be fixed in next release cycle |
+| 1 | **Low** | Fix when convenient, backlog-worthy |
+
+### Scope (1-3)
+| Score | Level | Description |
+|-------|-------|-------------|
+| 3 | **Broad** | Affects core path, multiple modules, or all users |
+| 2 | **Moderate** | Affects one module or a specific configuration |
+| 1 | **Narrow** | Affects edge case or single obscure path |
+
+**Bug severity score** = Impact × 2 + Urgency + Scope (base max 14)
+
+Apply a one-time +2 boost if any of the following are true (max 16):
+- Has a linked PR already (someone is working on it — fast-track review)
+- Is labeled `security`
+- Is a regression (worked before, broken now)
+
+## Step 5: Rank features by opportunity
+
+Score each feature request on these dimensions:
+
+### Value (1-4)
+| Score | Level | Description |
+|-------|-------|-------------|
+| 4 | **High** | Unlocks new use cases, frequently requested, strategic alignment |
+| 3 | **Medium-High** | Significant quality-of-life improvement, good user demand signals |
+| 2 | **Medium** | Nice to have, modest improvement to existing workflow |
+| 1 | **Low** | Marginal value, niche use case, unclear demand |
+
+Look for value signals in the issue:
+- Number of thumbs-up reactions or "+1" comments
+- Multiple people asking for the same thing
+- Alignment with project roadmap (check CLAUDE.md TODOs)
+- Unblocks other features or simplifies architecture
+
+### Effort estimate (1-3, inverted — lower effort = higher score)
+| Score | Level | Description |
+|-------|-------|-------------|
+| 3 | **Small** | <1 day, isolated change, clear implementation path |
+| 2 | **Medium** | 1-3 days, touches a few modules, some design needed |
+| 1 | **Large** | 3+ days, cross-cutting, needs RFC or architectural discussion |
+
+### Readiness (1-3)
+| Score | Level | Description |
+|-------|-------|-------------|
+| 3 | **Ready** | Well-specified, implementation path clear, no blockers |
+| 2 | **Almost ready** | Needs minor clarification, but scope is understood |
+| 1 | **Not ready** | Needs design discussion, has open questions, blocked by other work |
+
+**Opportunity score** = Value × 2 + Effort + Readiness (base max 14)
+
+Apply a one-time +2 boost if any of the following are true (max 16):
+- A community member offered to implement it
+- It has a linked draft PR
+- It closes a gap listed in the project's "Current Limitations / TODOs"
+
+## Step 6: Detect duplicates and relationships
+
+Check for:
+- **Duplicates** — Issues describing the same bug or requesting the same feature (compare titles and bodies)
+- **Related clusters** — Groups of issues around the same area (e.g., multiple workspace issues, multiple CLI issues)
+- **Already fixed** — Open issues that may have been resolved by recently closed issues or merged PRs
+- **Blockers** — Issues that reference other issues as prerequisites ("depends on #N", "blocked by #N")
+- **Epic candidates** — Multiple small issues that could be grouped under a single tracking issue
+
+## Step 7: Produce the triage report
+
+Present the output in this format:
+
+### Quick Stats
+
+```
+Open: N | Bugs: N | Features: N | Ambiguous: N
+Well-specified: N | Adequate: N | Under-specified: N
+Unassigned: N | Stale (>30d): N
+```
+
+---
+
+### Critical Bugs (Severity 12+)
+
+Bugs that need immediate attention. For each:
+
+| # | Title | Severity | Impact | Detail | Age | Assignee |
+|---|-------|----------|--------|--------|-----|----------|
+
+Include a 1-line summary of the root cause if discernible from the issue.
+
+### High-Priority Bugs (Severity 8-12)
+
+Same table format. These should be addressed in the next release cycle.
+
+### Medium/Low Bugs (Severity <8)
+
+Compact table, sorted by severity descending.
+
+---
+
+### Quick Wins (Opportunity 12+ AND Effort = Small)
+
+Features that are high-value and low-effort — do these first. For each:
+
+| # | Title | Opportunity | Value | Effort | Detail | Age |
+|---|-------|-------------|-------|--------|--------|-----|
+
+### High-Opportunity Features (Opportunity 10+)
+
+Same table format. Worth investing in.
+
+### Backlog Features (Opportunity <10)
+
+Compact table, sorted by opportunity descending.
+
+---
+
+### Under-Specified Issues (Need Clarification)
+
+Issues rated "Under-specified" that can't be triaged effectively. For each, suggest 1-2 specific questions to ask the author to make it actionable.
+
+| # | Title | Type | What's missing |
+|---|-------|------|---------------|
+
+### Ambiguous Issues (Bug or Feature?)
+
+Issues that couldn't be clearly classified. For each, explain the ambiguity and suggest which category it likely belongs in.
+
+---
+
+### Duplicates & Overlaps
+
+Groups of issues that appear to be duplicates or closely related. Recommend which to keep and which to close.
+
+### Already Fixed?
+
+Open issues that may have been resolved by recently closed issues or merged PRs.
+
+### Stale Issues (>30 days, no activity)
+
+Issues with no updates in 30+ days. Recommend: close, ping author, or keep.
+
+---
+
+### By Area
+
+Group all issues by the area of the codebase they affect (infer from title/body/labels):
+
+| Area | Bugs | Features | Top Priority |
+|------|------|----------|-------------|
+
+### Suggested Next Actions
+
+Based on the triage, provide 3-5 concrete recommendations:
+1. Which bugs to fix first and why
+2. Which quick-win features to pick up
+3. Which under-specified issues to clarify
+4. Which stale issues to close
+5. Any clusters that suggest a larger initiative
+
+## Rules
+
+- Use `gh` CLI for all GitHub operations. Never guess issue state — always check.
+- For large issue lists (>20), use the Task tool to parallelize fetching issue details and comments.
+- Be concise in summaries. One line per issue in tables.
+- When scoring, be honest about uncertainty. If you can't tell severity from the description, say so and rate it conservatively.
+- Factor in issue age — older unresolved bugs may indicate they're less critical than they seem, or that they're hard to fix. Note this in your assessment.
+- Check comment threads for additional context that the original body may lack. An under-specified issue with rich discussion may actually be well-understood.
+- Do NOT post comments, close issues, or take any action. This skill is read-only analysis.
+- If the repo has >100 open issues, focus the detailed analysis on the top 30 by recency and engagement (comments + reactions), and provide a summary table for the rest.

.claude/commands/triage-prs.md

@@ -0,0 +1,161 @@
+---
+description: Classify all open PRs by module, review state, scope, and architectural impact — produces a prioritized triage dashboard
+disable-model-invocation: true
+allowed-tools: Bash(gh pr list:*), Bash(gh pr view:*), Bash(gh pr diff:*), Bash(gh api:*), Bash(gh pr checks:*), Bash(git log:*), Read, Grep, Glob, Task
+argument-hint: "[--label=<filter>] [--author=<filter>]"
+---
+
+# PR Triage Dashboard
+
+You are triaging all open PRs on this repository. Your job is to produce a prioritized, module-grouped dashboard that tells the maintainer exactly which PRs need attention and in what order.
+
+## Step 1: Fetch all open PRs
+
+Fetch every open PR with metadata:
+
+```
+gh pr list --state open --limit 100 --json number,title,author,labels,additions,deletions,headRefName,createdAt,updatedAt,isDraft,reviewRequests,reviews,files,body
+```
+
+If `$ARGUMENTS` contains `--label=<X>`, append `--label '<X>'` to the `gh pr list` command. If it contains `--author=<X>`, append `--author '<X>'` to the command.
+
+Also fetch recently merged PRs (last 7 days) to detect superseded/conflicting work:
+
+```
+gh pr list --state merged --search "merged:>=$(date -v-7d +%Y-%m-%d)" --limit 100 --json number,title,body,mergedAt
+```
+
+## Step 2: Classify each PR by module
+
+For each open PR, determine the primary module it touches by examining the `files` field. Classify into these categories based on the dominant `src/` subdirectory:
+
+| Category | Directories |
+|----------|------------|
+| **LLM & Inference** | `src/llm/` |
+| **Agent Core** | `src/agent/`, `src/skills/` |
+| **Tools** | `src/tools/`, `tools-src/` |
+| **Channels** | `src/channels/`, `channels-src/` |
+| **Storage & Memory** | `src/db/`, `src/workspace/`, `migrations/` |
+| **Security** | `src/safety/`, `src/secrets/` |
+| **Config & Setup** | `src/config.rs`, `src/setup/`, `src/cli/` |
+| **Sandbox & Orchestration** | `src/sandbox/`, `src/orchestrator/`, `src/worker/` |
+| **Hooks & Extensions** | `src/hooks/`, `src/extensions/` |
+| **Context & History** | `src/context/`, `src/history/`, `src/estimation/`, `src/evaluation/` |
+| **Web Gateway** | `src/channels/web/` |
+| **CI/CD & Docs** | `.github/`, `README.md`, `CLAUDE.md`, `*.md` (no src) |
+| **Other** | Anything else |
+
+If a PR touches multiple modules, assign it to the **primary** module (most files changed) but note the cross-cutting modules.
+
+## Step 3: Assess review state
+
+For each PR, determine its review status:
+
+- **Approved** — At least one human APPROVED review, no outstanding CHANGES_REQUESTED
+- **Changes requested** — At least one CHANGES_REQUESTED review still unresolved
+- **Reviewed (comments only)** — Human comments but no formal approve/reject
+- **Automated only** — Only bot reviews (gemini-code-assist, copilot, etc.)
+- **No review** — No reviews at all
+
+Also check:
+- CI status: `gh pr checks {number}` — PASS / FAIL / NONE
+- Draft status: is the PR marked as draft?
+- Staleness: how many days since `updatedAt`?
+
+## Step 4: Determine scope and risk
+
+Classify each PR by scope:
+
+| Scope | Criteria |
+|-------|----------|
+| **Tiny** | <50 lines changed (additions + deletions), 1-2 files |
+| **Small** | 50-200 lines, 1-5 files |
+| **Medium** | 200-500 lines, 3-10 files |
+| **Large** | 500-2000 lines, 5-20 files |
+| **XL** | 2000+ lines or 20+ files |
+
+## Step 5: Classify as fix vs. architectural
+
+For each PR, determine its nature:
+
+### Fixes (merge fast)
+- Bug fixes with clear root cause
+- Security patches
+- Crash/panic prevention
+- Typo/doc corrections
+- Code quality (removing .unwrap(), etc.)
+
+### Features (standard review)
+- New functionality within existing patterns
+- New tool implementations
+- Configuration additions
+- Test additions
+
+### Architectural (deep review needed)
+- New modules or subsystems
+- Changes to core traits or interfaces
+- New database backends or storage engines
+- New provider abstractions
+- Changes touching 5+ modules
+- Anything modifying the agent loop, session model, or security layer
+- New dependencies (check Cargo.toml changes)
+
+## Step 6: Detect conflicts and superseded PRs
+
+Check for:
+- Multiple PRs fixing the same issue (look at "Closes #N" / "Fixes #N" in PR bodies)
+- PRs touching the same files (potential merge conflicts)
+- PRs that are follow-ups to other open PRs (dependency chains)
+- PRs superseded by recently merged work
+
+## Step 7: Produce the dashboard
+
+Present the output in this format:
+
+### Quick Stats
+```
+Open: N | Draft: N | Needs review: N | Changes requested: N | Ready to merge: N
+```
+
+### Ready to Merge
+PRs that are approved, CI passing, and non-draft. List with one-line summary.
+
+### Needs Human Review (Fixes)
+Fixes that have no human review yet, sorted by severity (security > crash > bug > quality).
+
+### Needs Human Review (Features)
+Features with no human review, sorted by scope (smallest first).
+
+### Needs Deep Architectural Review
+Large/XL PRs, new modules, or cross-cutting changes. For each, include:
+- Which modules are affected
+- What new patterns or abstractions are introduced
+- Key risk areas to focus review on
+
+### Changes Requested (Waiting on Author)
+PRs where a reviewer asked for changes. Include who requested and a 1-line summary of what's needed.
+
+### Stale / Blocked
+PRs with no activity >7 days, or blocked by other PRs.
+
+### Conflicts & Overlaps
+Any detected conflicts, superseded PRs, or dependency chains.
+
+### By Module
+Group all PRs by their primary module in a compact table:
+
+| Module | PRs | Key PR to review first |
+|--------|-----|----------------------|
+
+### Superseded PRs (recommend closing)
+PRs that are clearly superseded by merged work. Include reasoning.
+
+## Rules
+
+- Use `gh` CLI for all GitHub operations. Never guess PR state — always check.
+- For large PR lists (>15), use the Task tool to parallelize fetching PR details and diffs.
+- Be concise in summaries. One line per PR in tables.
+- When assessing "ready to merge", be conservative. If there's any unresolved concern from a repo member, it's not ready.
+- Flag any PR that has been open >14 days with no review as needing attention.
+- If a PR description says "Closes #N" but #N was already closed by another merged PR, flag it as potentially superseded.
+- Do NOT post comments or take any action on PRs. This skill is read-only analysis.

.env.example

@@ -2,14 +2,43 @@
 DATABASE_URL=postgres://localhost/ironclaw
 DATABASE_POOL_SIZE=10
 
-# LLM Provider (NEAR AI)
-# NEAR AI provides a unified interface to all models with user authentication
-# Session token is stored in ~/.ironclaw/session.json and managed automatically.
-# On first run, the agent will open a browser for OAuth authentication.
-NEARAI_MODEL=claude-3-5-sonnet-20241022
-NEARAI_BASE_URL=https://cloud-api.near.ai
+# LLM Provider
+# LLM_BACKEND=nearai           # default
+# Possible values: nearai, ollama, openai_compatible, openai, anthropic, tinfoil
+
+# === NEAR AI (Chat Completions API) ===
+# Two auth modes:
+#   1. Session token (default): Uses browser OAuth (GitHub/Google) on first run.
+#      Session token stored in ~/.ironclaw/session.json automatically.
+#      Base URL defaults to https://private.near.ai
+#   2. API key: Set NEARAI_API_KEY to use API key auth from cloud.near.ai.
+#      Base URL defaults to https://cloud-api.near.ai
+NEARAI_MODEL=zai-org/GLM-5-FP8
+NEARAI_BASE_URL=https://private.near.ai
 NEARAI_AUTH_URL=https://private.near.ai
-# NEARAI_SESSION_PATH=~/.ironclaw/session.json  # optional, default shown
+# NEARAI_SESSION_TOKEN=sess_...                  # hosting providers: set this
+# NEARAI_SESSION_PATH=~/.ironclaw/session.json   # optional, default shown
+# NEARAI_API_KEY=...                             # API key from cloud.near.ai
+
+# Local LLM Providers (Ollama, LM Studio, vLLM, LiteLLM)
+
+# === Ollama ===
+# OLLAMA_MODEL=llama3.2
+# LLM_BACKEND=ollama
+# OLLAMA_BASE_URL=http://localhost:11434   # default
+
+# === OpenAI-compatible (LM Studio, vLLM, Anything-LLM) ===
+# LLM_MODEL=llama-3.2-3b-instruct-q4_K_M
+# LLM_BACKEND=openai_compatible
+# LLM_BASE_URL=http://localhost:1234/v1
+# LLM_API_KEY=sk-...                        # optional for local servers
+
+# === OpenRouter (via OpenAI-compatible) ===
+# LLM_MODEL=anthropic/claude-sonnet-4
+# LLM_BACKEND=openai_compatible
+# LLM_BASE_URL=https://openrouter.ai/api/v1
+# LLM_API_KEY=sk-or-...
+
 
 # Channel Configuration
 # CLI is always enabled
@@ -46,6 +75,12 @@ HEARTBEAT_INTERVAL_SECS=1800
 HEARTBEAT_NOTIFY_CHANNEL=cli
 HEARTBEAT_NOTIFY_USER=default
 
+# Memory hygiene settings (automatic cleanup of stale workspace documents)
+# Runs on each heartbeat tick; identity files (IDENTITY.md, SOUL.md) are never deleted
+# MEMORY_HYGIENE_ENABLED=true
+# MEMORY_HYGIENE_RETENTION_DAYS=30     # delete daily/ docs older than this many days
+# MEMORY_HYGIENE_CADENCE_HOURS=12      # minimum hours between cleanup passes
+
 # Safety settings
 SAFETY_MAX_OUTPUT_LENGTH=100000
 SAFETY_INJECTION_CHECK_ENABLED=true

.github/labeler.yml

@@ -0,0 +1,166 @@
+# Scope labels for actions/labeler@v6
+# Maps file path globs to scope labels. Multiple labels can apply per PR.
+
+"scope: agent":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/agent/**
+
+"scope: channel":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/channels/channel.rs
+          - src/channels/manager.rs
+          - src/channels/mod.rs
+
+"scope: channel/cli":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/channels/cli/**
+          - src/cli/**
+
+"scope: channel/web":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/channels/web/**
+
+"scope: channel/wasm":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/channels/wasm/**
+
+"scope: tool":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/tools/tool.rs
+          - src/tools/registry.rs
+          - src/tools/mod.rs
+          - src/tools/sandbox.rs
+
+"scope: tool/builtin":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/tools/builtin/**
+
+"scope: tool/wasm":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/tools/wasm/**
+
+"scope: tool/mcp":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/tools/mcp/**
+
+"scope: tool/builder":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/tools/builder/**
+
+"scope: db":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/db/mod.rs
+
+"scope: db/postgres":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/db/postgres.rs
+          - migrations/**
+
+"scope: db/libsql":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/db/libsql_backend.rs
+          - src/db/libsql_migrations.rs
+
+"scope: safety":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/safety/**
+
+"scope: llm":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/llm/**
+
+"scope: workspace":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/workspace/**
+
+"scope: orchestrator":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/orchestrator/**
+
+"scope: worker":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/worker/**
+
+"scope: secrets":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/secrets/**
+
+"scope: config":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/config.rs
+          - src/settings.rs
+
+"scope: extensions":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/extensions/**
+
+"scope: setup":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/setup/**
+
+"scope: evaluation":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/evaluation/**
+
+"scope: estimation":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/estimation/**
+
+"scope: sandbox":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/sandbox/**
+          - Dockerfile*
+
+"scope: hooks":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/hooks/**
+
+"scope: pairing":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/pairing/**
+
+"scope: ci":
+  - changed-files:
+      - any-glob-to-any-file:
+          - .github/workflows/**
+          - .github/scripts/**
+
+"scope: docs":
+  - changed-files:
+      - any-glob-to-any-file:
+          - "**/*.md"
+          - docs/**
+          - LICENSE*
+
+"scope: dependencies":
+  - changed-files:
+      - any-glob-to-any-file:
+          - Cargo.toml
+          - Cargo.lock

.github/scripts/create-labels.sh

@@ -0,0 +1,71 @@
+#!/usr/bin/env bash
+# Idempotent label bootstrap for IronClaw PR automation.
+# Uses `gh label create --force` so it can be re-run safely.
+#
+# Usage: bash .github/scripts/create-labels.sh
+# Requires: gh CLI authenticated with repo scope
+
+set -euo pipefail
+
+if ! command -v gh &>/dev/null; then
+  echo "Error: gh CLI is required. Install from https://cli.github.com" >&2
+  exit 1
+fi
+
+create() {
+  local name="$1" color="$2" description="$3"
+  gh label create "$name" --color "$color" --description "$description" --force
+}
+
+echo "==> Creating size labels..."
+create "size: XS"    "F9D0C4" "< 10 changed lines (excluding docs)"
+create "size: S"     "F5A3A3" "10-49 changed lines"
+create "size: M"     "E57373" "50-199 changed lines"
+create "size: L"     "D32F2F" "200-499 changed lines"
+create "size: XL"    "B71C1C" "500+ changed lines"
+
+echo "==> Creating risk labels..."
+create "risk: low"    "4CAF50" "Changes to docs, tests, or low-risk modules"
+create "risk: medium" "FFC107" "Business logic, config, or moderate-risk modules"
+create "risk: high"   "F44336" "Safety, secrets, auth, or critical infrastructure"
+create "risk: manual" "9E9E9E" "Risk level set manually (sticky, not overwritten)"
+
+echo "==> Creating scope labels..."
+create "scope: agent"         "006B75" "Agent core (agent loop, router, scheduler)"
+create "scope: channel"       "00838F" "Channel infrastructure"
+create "scope: channel/cli"   "00897B" "TUI / CLI channel"
+create "scope: channel/web"   "00796B" "Web gateway channel"
+create "scope: channel/wasm"  "00695C" "WASM channel runtime"
+create "scope: tool"          "1565C0" "Tool infrastructure"
+create "scope: tool/builtin"  "1976D2" "Built-in tools"
+create "scope: tool/wasm"     "1E88E5" "WASM tool sandbox"
+create "scope: tool/mcp"      "2196F3" "MCP client"
+create "scope: tool/builder"  "42A5F5" "Dynamic tool builder"
+create "scope: db"            "4A148C" "Database trait / abstraction"
+create "scope: db/postgres"   "6A1B9A" "PostgreSQL backend"
+create "scope: db/libsql"     "7B1FA2" "libSQL / Turso backend"
+create "scope: safety"        "880E4F" "Prompt injection defense"
+create "scope: llm"           "4527A0" "LLM integration"
+create "scope: workspace"     "283593" "Persistent memory / workspace"
+create "scope: orchestrator"  "0D47A1" "Container orchestrator"
+create "scope: worker"        "01579B" "Container worker"
+create "scope: secrets"       "BF360C" "Secrets management"
+create "scope: config"        "E65100" "Configuration"
+create "scope: extensions"    "33691E" "Extension management"
+create "scope: setup"         "827717" "Onboarding / setup"
+create "scope: evaluation"    "558B2F" "Success evaluation"
+create "scope: estimation"    "9E9D24" "Cost/time estimation"
+create "scope: sandbox"       "00BFA5" "Docker sandbox"
+create "scope: hooks"         "6D4C41" "Git/event hooks"
+create "scope: pairing"       "4E342E" "Pairing mode"
+create "scope: ci"            "546E7A" "CI/CD workflows"
+create "scope: docs"          "78909C" "Documentation"
+create "scope: dependencies"  "90A4AE" "Dependency updates"
+
+echo "==> Creating contributor labels..."
+create "contributor: new"         "FFF9C4" "First-time contributor"
+create "contributor: regular"     "FFE082" "2-5 merged PRs"
+create "contributor: experienced" "FFB74D" "6-19 merged PRs"
+create "contributor: core"        "FF8A65" "20+ merged PRs"
+
+echo "Done. All labels created/updated."

.github/scripts/pr-labeler.sh

@@ -0,0 +1,139 @@
+#!/usr/bin/env bash
+# Classify a PR by size, risk, and contributor tier.
+# Called by the pr-label-classify workflow.
+#
+# Inputs (env vars):
+#   PR_NUMBER  — pull request number
+#   REPO       — owner/repo (e.g. "user/ironclaw")
+#
+# Requires: gh CLI, jq
+
+set -euo pipefail
+
+PR_NUMBER="${PR_NUMBER:?PR_NUMBER is required}"
+REPO="${REPO:?REPO is required}"
+
+# ─── helpers ────────────────────────────────────────────────────────────────
+
+# Remove all labels in a dimension except the desired one.
+# Usage: set_exclusive_label "size" "size: M"
+set_exclusive_label() {
+  local prefix="$1" desired="$2"
+
+  # Fetch current labels on the PR
+  local current
+  current=$(gh pr view "$PR_NUMBER" --repo "$REPO" --json labels --jq '.labels[].name')
+
+  # Remove any existing label with the same prefix
+  while IFS= read -r label; do
+    [[ -z "$label" ]] && continue
+    if [[ "$label" == "${prefix}:"* && "$label" != "$desired" ]]; then
+      gh pr edit "$PR_NUMBER" --repo "$REPO" --remove-label "$label" 2>/dev/null || true
+    fi
+  done <<< "$current"
+
+  # Add the desired label
+  gh pr edit "$PR_NUMBER" --repo "$REPO" --add-label "$desired"
+}
+
+# ─── size ───────────────────────────────────────────────────────────────────
+
+classify_size() {
+  # Sum changed lines across non-doc files
+  local total
+  total=$(gh api "repos/${REPO}/pulls/${PR_NUMBER}/files" \
+    --paginate --jq '
+      [.[] | select(.filename | test("\\.(md|txt|rst|adoc)$") | not) | .changes]
+      | add // 0
+    ')
+
+  local label
+  if   (( total < 10 ));  then label="size: XS"
+  elif (( total < 50 ));  then label="size: S"
+  elif (( total < 200 )); then label="size: M"
+  elif (( total < 500 )); then label="size: L"
+  else                         label="size: XL"
+  fi
+
+  echo "Size: ${total} changed lines -> ${label}"
+  set_exclusive_label "size" "$label"
+}
+
+# ─── risk ───────────────────────────────────────────────────────────────────
+
+classify_risk() {
+  # If "risk: manual" is present, skip — it's a sticky override
+  local current
+  current=$(gh pr view "$PR_NUMBER" --repo "$REPO" --json labels --jq '.labels[].name')
+  if echo "$current" | grep -qx "risk: manual"; then
+    echo "Risk: skipped (manual override)"
+    return
+  fi
+
+  # Fetch changed file paths
+  local files
+  files=$(gh api "repos/${REPO}/pulls/${PR_NUMBER}/files" \
+    --paginate --jq '.[].filename')
+
+  local risk="low"
+
+  while IFS= read -r file; do
+    [[ -z "$file" ]] && continue
+
+    case "$file" in
+      # High risk: safety, secrets, auth, crypto, setup, orchestrator auth
+      src/safety/*|src/secrets/*|src/llm/session.rs|src/orchestrator/auth.rs|\
+      src/channels/web/auth.rs|src/setup/*)
+        risk="high"
+        break  # can't go higher
+        ;;
+
+      # Medium risk: agent core, config, database, worker, tools, channels
+      src/agent/*|src/config.rs|src/settings.rs|src/db/*|src/worker/*|\
+      src/tools/*|src/channels/*|src/orchestrator/*|src/context/*|\
+      src/hooks/*|src/sandbox/*|src/extensions/*|Cargo.toml|\
+      .github/workflows/*)
+        # Only upgrade, never downgrade
+        [[ "$risk" != "high" ]] && risk="medium"
+        ;;
+
+      # Low risk: docs, tests, estimation, evaluation, history, etc.
+      *)
+        ;;
+    esac
+  done <<< "$files"
+
+  echo "Risk: ${risk}"
+  set_exclusive_label "risk" "risk: ${risk}"
+}
+
+# ─── contributor tier ───────────────────────────────────────────────────────
+
+classify_contributor() {
+  # Get PR author
+  local author
+  author=$(gh pr view "$PR_NUMBER" --repo "$REPO" --json author --jq '.author.login')
+
+  # Count merged PRs by this author in this repo
+  local count
+  count=$(gh pr list --repo "$REPO" --state merged --author "$author" \
+    --limit 100 --json number --jq 'length')
+
+  local label
+  if   (( count == 0 )); then label="contributor: new"
+  elif (( count < 6 ));  then label="contributor: regular"
+  elif (( count < 20 )); then label="contributor: experienced"
+  else                        label="contributor: core"
+  fi
+
+  echo "Contributor: ${author} has ${count} merged PRs -> ${label}"
+  set_exclusive_label "contributor" "$label"
+}
+
+# ─── main ───────────────────────────────────────────────────────────────────
+
+echo "Classifying PR #${PR_NUMBER} in ${REPO}..."
+classify_size
+classify_risk
+classify_contributor
+echo "Done."

.github/workflows/pr-label-classify.yml

@@ -0,0 +1,26 @@
+name: "PR: Classify (Size, Risk, Contributor)"
+
+on:
+  pull_request_target:
+    types: [opened, synchronize, reopened]
+
+permissions:
+  contents: read
+  pull-requests: write
+  issues: read           # needed for search/issues API (contributor count)
+
+jobs:
+  classify:
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout base branch
+        uses: actions/checkout@v4
+        with:
+          ref: ${{ github.event.pull_request.base.ref }}
+
+      - name: Classify PR
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+          PR_NUMBER: ${{ github.event.pull_request.number }}
+          REPO: ${{ github.repository }}
+        run: bash .github/scripts/pr-labeler.sh

.github/workflows/pr-label-scope.yml

@@ -0,0 +1,18 @@
+name: "PR: Scope Labels"
+
+on:
+  pull_request_target:
+    types: [opened, synchronize, reopened]
+
+permissions:
+  contents: read
+  pull-requests: write
+
+jobs:
+  scope:
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/labeler@v5
+        with:
+          configuration-path: .github/labeler.yml
+          sync-labels: false          # additive only — never remove scope labels

.gitignore

@@ -13,6 +13,9 @@
 
 target/
 
+# Benchmark results (local runs, not committed)
+bench-results/
+
 # WASM build artifacts (loaded from disk, not bundled)
 *.wasm
 

CHANGELOG.md

@@ -7,6 +7,108 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## [Unreleased]
 
+## [0.9.0](https://github.com/nearai/ironclaw/compare/v0.8.0...v0.9.0) - 2026-02-21
+
+### Added
+
+- add TEE attestation shield to web gateway UI ([#275](https://github.com/nearai/ironclaw/pull/275))
+- configurable tool iterations, auto-approve, and policy fix ([#251](https://github.com/nearai/ironclaw/pull/251))
+
+### Fixed
+
+- add X-Accel-Buffering header to SSE endpoints ([#277](https://github.com/nearai/ironclaw/pull/277))
+
+## [0.8.0](https://github.com/nearai/ironclaw/compare/ironclaw-v0.7.0...ironclaw-v0.8.0) - 2026-02-20
+
+### Added
+
+- extension registry with metadata catalog and onboarding integration ([#238](https://github.com/nearai/ironclaw/pull/238))
+- *(models)* add GPT-5.3 Codex, full GPT-5.x family, Claude 4.x series, o4-mini ([#197](https://github.com/nearai/ironclaw/pull/197))
+- wire memory hygiene into the heartbeat loop ([#195](https://github.com/nearai/ironclaw/pull/195))
+
+### Fixed
+
+- persist WASM channel workspace writes across callbacks ([#264](https://github.com/nearai/ironclaw/pull/264))
+- consolidate per-module ENV_MUTEX into crate-wide test lock ([#246](https://github.com/nearai/ironclaw/pull/246))
+- remove auto-proceed fake user message injection from agent loop ([#255](https://github.com/nearai/ironclaw/pull/255))
+- onboarding errors reset flow and remote server auth (#185, #186) ([#248](https://github.com/nearai/ironclaw/pull/248))
+- parallelize tool call execution via JoinSet ([#219](https://github.com/nearai/ironclaw/pull/219)) ([#252](https://github.com/nearai/ironclaw/pull/252))
+- prevent pipe deadlock in shell command execution ([#140](https://github.com/nearai/ironclaw/pull/140))
+- persist turns after approval and add agent-level tests ([#250](https://github.com/nearai/ironclaw/pull/250))
+
+### Other
+
+- add automated PR labeling system ([#253](https://github.com/nearai/ironclaw/pull/253))
+- update CLAUDE.md for recently merged features ([#183](https://github.com/nearai/ironclaw/pull/183))
+
+## [0.7.0](https://github.com/nearai/ironclaw/compare/ironclaw-v0.6.0...ironclaw-v0.7.0) - 2026-02-19
+
+### Added
+
+- extend lifecycle hooks with declarative bundles ([#176](https://github.com/nearai/ironclaw/pull/176))
+- support per-request model override in /v1/chat/completions ([#103](https://github.com/nearai/ironclaw/pull/103))
+
+### Fixed
+
+- harden openai-compatible provider, approval replay, and embeddings defaults ([#237](https://github.com/nearai/ironclaw/pull/237))
+- Network Security Findings ([#201](https://github.com/nearai/ironclaw/pull/201))
+
+### Added
+
+- Refactored OpenAI-compatible chat completion routing to use the rig adapter and `RetryProvider` composition for custom base URL usage.
+- Added Ollama embeddings provider support (`EMBEDDING_PROVIDER=ollama`, `OLLAMA_BASE_URL`) in workspace embeddings.
+- Added migration `V9__flexible_embedding_dimension.sql` for flexible embedding vector dimensions.
+
+### Changed
+
+- Changed default sandbox image to `ironclaw-worker:latest` in config/settings/sandbox defaults.
+- Improved tool-message sanitization and provider compatibility handling across NEAR AI, rig adapter, and shared LLM provider code.
+
+### Fixed
+
+- Fixed approval-input aliases (`a`, `/approve`, `/always`, `/deny`, etc.) in submission parsing.
+- Fixed multi-tool approval resume flow by preserving and replaying deferred tool calls so all prior `tool_use` IDs receive matching `tool_result` messages.
+- Fixed REPL quit/exit handling to route shutdown through the agent loop for graceful termination.
+
+## [0.6.0](https://github.com/nearai/ironclaw/compare/ironclaw-v0.5.0...ironclaw-v0.6.0) - 2026-02-19
+
+### Added
+
+- add issue triage skill ([#200](https://github.com/nearai/ironclaw/pull/200))
+- add PR triage dashboard skill ([#196](https://github.com/nearai/ironclaw/pull/196))
+- add OpenRouter usage examples ([#189](https://github.com/nearai/ironclaw/pull/189))
+- add Tinfoil private inference provider ([#62](https://github.com/nearai/ironclaw/pull/62))
+- shell env scrubbing and command injection detection ([#164](https://github.com/nearai/ironclaw/pull/164))
+- Add PR review tools, job monitor, and channel injection for E2E sandbox workflows ([#57](https://github.com/nearai/ironclaw/pull/57))
+- Secure prompt-based skills system (Phases 1-4) ([#51](https://github.com/nearai/ironclaw/pull/51))
+- Add benchmarking harness with spot suite ([#10](https://github.com/nearai/ironclaw/pull/10))
+- 10 infrastructure improvements from zeroclaw ([#126](https://github.com/nearai/ironclaw/pull/126))
+
+### Fixed
+
+- *(rig)* prevent OpenAI Responses API panic on tool call IDs ([#182](https://github.com/nearai/ironclaw/pull/182))
+- *(docs)* correct settings storage path in README ([#194](https://github.com/nearai/ironclaw/pull/194))
+- OpenAI tool calling — schema normalization, missing types, and Responses API panic ([#132](https://github.com/nearai/ironclaw/pull/132))
+- *(security)* prevent path traversal bypass in WASM HTTP allowlist ([#137](https://github.com/nearai/ironclaw/pull/137))
+- persist OpenAI-compatible provider and respect embeddings disable ([#177](https://github.com/nearai/ironclaw/pull/177))
+- remove .expect() calls in FailoverProvider::try_providers ([#156](https://github.com/nearai/ironclaw/pull/156))
+- sentinel value collision in FailoverProvider cooldown ([#125](https://github.com/nearai/ironclaw/pull/125)) ([#154](https://github.com/nearai/ironclaw/pull/154))
+- skills module audit cleanup ([#173](https://github.com/nearai/ironclaw/pull/173))
+
+### Other
+
+- Fix division by zero panic in ValueEstimator::is_profitable ([#139](https://github.com/nearai/ironclaw/pull/139))
+- audit feature parity matrix against codebase and recent commits ([#202](https://github.com/nearai/ironclaw/pull/202))
+- architecture improvements for contributor velocity ([#198](https://github.com/nearai/ironclaw/pull/198))
+- fix rustfmt formatting from PR #137
+- add .env.example examples for Ollama and OpenAI-compatible ([#110](https://github.com/nearai/ironclaw/pull/110))
+
+## [0.5.0](https://github.com/nearai/ironclaw/compare/v0.4.0...v0.5.0) - 2026-02-17
+
+### Added
+
+- add cooldown management to FailoverProvider ([#114](https://github.com/nearai/ironclaw/pull/114))
+
 ## [0.4.0](https://github.com/nearai/ironclaw/compare/v0.3.0...v0.4.0) - 2026-02-17
 
 ### Added
@@ -55,6 +157,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Bump MSRV to 1.92, add GCP deployment files ([#40](https://github.com/nearai/ironclaw/pull/40))
 - Add OpenAI-compatible HTTP API (/v1/chat/completions, /v1/models)   ([#31](https://github.com/nearai/ironclaw/pull/31))
 
+
 ## [0.1.3](https://github.com/nearai/ironclaw/compare/v0.1.2...v0.1.3) - 2026-02-12
 
 ### Other

CLAUDE.md

@@ -13,14 +13,17 @@
 ### Features
 - **Multi-channel input**: TUI (Ratatui), HTTP webhooks, WASM channels (Telegram, Slack), web gateway
 - **Parallel job execution** with state machine and self-repair for stuck jobs
-- **Sandbox execution**: Docker container isolation with orchestrator/worker pattern
+- **Sandbox execution**: Docker container isolation with network proxy and credential injection
 - **Claude Code mode**: Delegate jobs to Claude CLI inside containers
+- **Skills system**: SKILL.md prompt extensions with trust model, tool attenuation, and ClawHub registry
 - **Routines**: Scheduled (cron) and reactive (event, webhook) task execution
 - **Web gateway**: Browser UI with SSE/WebSocket real-time streaming
 - **Extension management**: Install, auth, activate MCP/WASM extensions
 - **Extensible tools**: Built-in tools, WASM sandbox, MCP client, dynamic builder
 - **Persistent memory**: Workspace with hybrid search (FTS + vector via RRF)
-- **Prompt injection defense**: Sanitizer, validator, policy rules, leak detection
+- **Prompt injection defense**: Sanitizer, validator, policy rules, leak detection, shell env scrubbing
+- **Multi-provider LLM**: NEAR AI, OpenAI, Anthropic, Ollama, OpenAI-compatible, Tinfoil private inference
+- **Setup wizard**: 7-step interactive onboarding for first-run configuration
 - **Heartbeat system**: Proactive periodic execution with checklist
 
 ## Build & Test
@@ -64,6 +67,7 @@ src/
 │   ├── context_monitor.rs # Memory pressure detection
 │   ├── undo.rs         # Turn-based undo/redo with checkpoints
 │   ├── submission.rs   # Submission parsing (undo, redo, compact, clear, etc.)
+│   ├── dispatcher.rs   # Skill-aware job dispatching
 │   ├── task.rs         # Sub-task execution framework
 │   ├── routine.rs      # Routine types (Trigger, Action, Guardrails)
 │   └── routine_engine.rs # Routine execution (cron ticker, event matcher)
@@ -113,11 +117,18 @@ src/
 │   ├── policy.rs       # PolicyRule system with severity/actions
 │   └── leak_detector.rs # Secret detection (API keys, tokens, etc.)
 │
-├── llm/                # LLM integration (NEAR AI only)
+├── llm/                # LLM integration (multi-provider)
+│   ├── mod.rs          # Provider factory, LlmBackend enum
 │   ├── provider.rs     # LlmProvider trait, message types
-│   ├── nearai.rs       # NEAR AI chat-api implementation
+│   ├── nearai_chat.rs  # NEAR AI Chat Completions provider (session token + API key auth)
 │   ├── reasoning.rs    # Planning, tool selection, evaluation
-│   └── session.rs      # Session token management with auto-renewal
+│   ├── session.rs      # Session token management with auto-renewal
+│   ├── circuit_breaker.rs # Circuit breaker for provider failures
+│   ├── retry.rs        # Retry with exponential backoff
+│   ├── failover.rs     # Multi-provider failover chain
+│   ├── response_cache.rs # LLM response caching
+│   ├── costs.rs        # Token cost tracking
+│   └── rig_adapter.rs  # Rig framework adapter
 │
 ├── tools/              # Extensible tool system
 │   ├── tool.rs         # Tool trait, ToolOutput, ToolError
@@ -131,6 +142,7 @@ src/
 │   │   ├── job.rs      # CreateJob, ListJobs, JobStatus, CancelJob
 │   │   ├── routine.rs  # routine_create/list/update/delete/history
 │   │   ├── extension_tools.rs # Extension install/auth/activate/remove
+│   │   ├── skill_tools.rs # skill_list/search/install/remove tools
 │   │   └── marketplace.rs, ecommerce.rs, taskrabbit.rs, restaurant.rs (stubs)
 │   ├── builder/        # Dynamic tool building
 │   │   ├── core.rs     # BuildRequirement, SoftwareType, Language
@@ -180,11 +192,38 @@ src/
 │   ├── success.rs      # SuccessEvaluator trait, RuleBasedEvaluator, LlmEvaluator
 │   └── metrics.rs      # MetricsCollector, QualityMetrics
 │
+├── sandbox/            # Docker execution sandbox
+│   ├── mod.rs          # Public API, default allowlist
+│   ├── config.rs       # SandboxConfig, SandboxPolicy enum
+│   ├── manager.rs      # SandboxManager orchestration
+│   ├── container.rs    # ContainerRunner, Docker lifecycle
+│   ├── error.rs        # SandboxError types
+│   └── proxy/          # Network proxy for containers
+│       ├── mod.rs      # NetworkProxyBuilder
+│       ├── http.rs     # HttpProxy, CredentialResolver trait
+│       ├── policy.rs   # NetworkPolicyDecider trait
+│       └── allowlist.rs # DomainAllowlist validation
+│
 ├── secrets/            # Secrets management
 │   ├── crypto.rs       # AES-256-GCM encryption
 │   ├── store.rs        # Secret storage
 │   └── types.rs        # Credential types
 │
+├── setup/              # Onboarding wizard (spec: src/setup/README.md)
+│   ├── mod.rs          # Entry point, check_onboard_needed()
+│   ├── wizard.rs       # 7-step interactive wizard
+│   ├── channels.rs     # Channel setup helpers
+│   └── prompts.rs      # Terminal prompts (select, confirm, secret)
+│
+├── skills/             # SKILL.md prompt extension system
+│   ├── mod.rs          # Core types (SkillTrust, LoadedSkill)
+│   ├── registry.rs     # SkillRegistry: discover, install, remove
+│   ├── selector.rs     # Deterministic scoring prefilter
+│   ├── attenuation.rs  # Trust-based tool ceiling
+│   ├── gating.rs       # Requirement checks (bins, env, config)
+│   ├── parser.rs       # SKILL.md frontmatter + markdown parser
+│   └── catalog.rs      # ClawHub registry client
+│
 └── history/            # Persistence
     ├── store.rs        # PostgreSQL repositories
     └── analytics.rs    # Aggregation queries (JobStats, ToolStats)
@@ -214,6 +253,7 @@ When designing new features or systems, always prefer generic/extensible archite
 - `LlmProvider` - Add new LLM backends
 - `SuccessEvaluator` - Custom evaluation logic
 - `EmbeddingProvider` - Add embedding backends (workspace search)
+- `NetworkPolicyDecider` - Custom network access policies for sandbox containers
 
 ### Tool Implementation
 ```rust
@@ -252,6 +292,40 @@ Pending -> InProgress -> Completed -> Submitted -> Accepted
                               \-> Failed
 ```
 
+### Code Style
+
+- Use `crate::` imports, not `super::`
+- No `pub use` re-exports unless exposing to downstream consumers
+- Prefer strong types over strings (enums, newtypes)
+- Keep functions focused, extract helpers when logic is reused
+- Comments for non-obvious logic only
+
+### Review & Fix Discipline
+
+Hard-won lessons from code review -- follow these when fixing bugs or addressing review feedback.
+
+**Fix the pattern, not just the instance:** When a reviewer flags a bug (e.g., TOCTOU race in INSERT + SELECT-back), search the entire codebase for all instances of that same pattern. A fix in `SecretsStore::create()` that doesn't also fix `WasmToolStore::store()` is half a fix.
+
+**Propagate architectural fixes to satellite types:** If a core type changes its concurrency model (e.g., `LibSqlBackend` switches to connection-per-operation), every type that was handed a resource from the old model (e.g., `LibSqlSecretsStore`, `LibSqlWasmToolStore` holding a single `Connection`) must also be updated. Grep for the old type across the codebase.
+
+**Schema translation is more than DDL:** When translating a database schema between backends (PostgreSQL to libSQL, etc.), check for:
+- **Indexes** -- diff `CREATE INDEX` statements between the two schemas
+- **Seed data** -- check for `INSERT INTO` in migrations (e.g., `leak_detection_patterns`)
+- **Semantic differences** -- document where SQL functions behave differently (e.g., `json_patch` vs `jsonb_set`)
+
+**Feature flag testing:** When adding feature-gated code, test compilation with each feature in isolation:
+```bash
+cargo check                                          # default features
+cargo check --no-default-features --features libsql  # libsql only
+cargo check --all-features                           # all features
+```
+Dead code behind the wrong `#[cfg]` gate will only show up when building with a single feature.
+
+**Mechanical verification before committing:** Run these checks on changed files before committing:
+- `grep -rnE '\.unwrap\(|\.expect\(' <files>` -- no panics in production
+- `grep -rn 'super::' <files>` -- use `crate::` imports
+- If you fixed a pattern bug, `grep` for other instances of that pattern across `src/`
+
 ## Configuration
 
 Environment variables (see `.env.example`):
@@ -263,10 +337,14 @@ LIBSQL_PATH=~/.ironclaw/ironclaw.db    # libSQL local path (default)
 # LIBSQL_URL=libsql://xxx.turso.io    # Turso cloud (optional)
 # LIBSQL_AUTH_TOKEN=xxx                # Required with LIBSQL_URL
 
-# NEAR AI (required)
-NEARAI_SESSION_TOKEN=sess_...
-NEARAI_MODEL=claude-3-5-sonnet-20241022
+# NEAR AI (when LLM_BACKEND=nearai, the default)
+# Two auth modes: session token (default) or API key
+# Session token auth (default): uses browser OAuth on first run
+NEARAI_SESSION_TOKEN=sess_...           # hosting providers: set this
 NEARAI_BASE_URL=https://private.near.ai
+# API key auth: set NEARAI_API_KEY, base URL defaults to cloud-api.near.ai
+# NEARAI_API_KEY=...                    # API key from cloud.near.ai
+NEARAI_MODEL=claude-3-5-sonnet-20241022
 
 # Agent settings
 AGENT_NAME=ironclaw
@@ -297,6 +375,10 @@ SANDBOX_ENABLED=true
 SANDBOX_IMAGE=ironclaw-worker:latest
 SANDBOX_MEMORY_LIMIT_MB=512
 SANDBOX_TIMEOUT_SECS=1800
+SANDBOX_CPU_LIMIT=1.0                  # CPU cores per container
+SANDBOX_NETWORK_PROXY=true             # Enable network proxy for containers
+SANDBOX_PROXY_PORT=8080                # Proxy listener port
+SANDBOX_DEFAULT_POLICY=workspace_write # ReadOnly, WorkspaceWrite, FullAccess
 
 # Claude Code mode (runs inside sandbox containers)
 CLAUDE_CODE_ENABLED=false
@@ -308,16 +390,25 @@ CLAUDE_CODE_CONFIG_DIR=/home/worker/.claude
 ROUTINES_ENABLED=true
 ROUTINES_CRON_INTERVAL=60            # Tick interval in seconds
 ROUTINES_MAX_CONCURRENT=3
+
+# Skills system
+SKILLS_ENABLED=true
+SKILLS_MAX_TOKENS=4000                 # Max prompt budget per turn
+SKILLS_CATALOG_URL=https://clawhub.dev # ClawHub registry URL
+SKILLS_AUTO_DISCOVER=true              # Scan skill directories on startup
+
+# Tinfoil private inference
+TINFOIL_API_KEY=...                    # Required when LLM_BACKEND=tinfoil
+TINFOIL_MODEL=kimi-k2-5               # Default model
 ```
 
-### NEAR AI Provider
+### LLM Providers
 
-Uses the NEAR AI chat-api (`https://api.near.ai/v1/responses`) which provides:
-- Unified access to multiple models (OpenAI, Anthropic, etc.)
-- User authentication via session tokens
-- Usage tracking and billing through NEAR AI
+IronClaw supports multiple LLM backends via the `LLM_BACKEND` env var: `nearai` (default), `openai`, `anthropic`, `ollama`, `openai_compatible`, and `tinfoil`.
 
-Session tokens have the format `sess_xxx` (37 characters). They are authenticated against the NEAR AI auth service.
+**NEAR AI** -- Uses the Chat Completions API with dual auth support. Session token auth (default): authenticates with session tokens (`sess_xxx`) obtained via browser OAuth (GitHub/Google), base URL defaults to `https://private.near.ai`. API key auth: set `NEARAI_API_KEY` (from `cloud.near.ai`), base URL defaults to `https://cloud-api.near.ai`. Both modes use the same Chat Completions endpoint. Tool messages are flattened to plain text for compatibility. Set `NEARAI_SESSION_TOKEN` env var for hosting providers that inject tokens via environment.
+
+**Tinfoil** -- Private inference via `https://inference.tinfoil.sh/v1`. Runs models inside hardware-attested TEEs so neither Tinfoil nor the cloud provider can see prompts or responses. Uses the OpenAI-compatible Chat Completions API. Configure with `TINFOIL_API_KEY` and `TINFOIL_MODEL` (default: `kimi-k2-5`).
 
 ## Database
 
@@ -386,22 +477,7 @@ Both backends implement this trait. PostgreSQL delegates to the existing `Store`
 - `tool_failures` - Self-repair tracking
 - `secrets`, `wasm_tools`, `tool_capabilities` - Extension infrastructure
 
-### Configuration
-
-```bash
-# Backend selection (default: postgres)
-DATABASE_BACKEND=libsql
-
-# PostgreSQL
-DATABASE_URL=postgres://user:pass@localhost/ironclaw
-
-# libSQL (embedded)
-LIBSQL_PATH=~/.ironclaw/ironclaw.db    # Default path
-
-# libSQL (Turso cloud sync)
-LIBSQL_URL=libsql://your-db.turso.io
-LIBSQL_AUTH_TOKEN=your-token            # Required when LIBSQL_URL is set
-```
+Database configuration: see Configuration section above.
 
 ### Current Limitations (libSQL backend)
 
@@ -419,6 +495,7 @@ All external tool output passes through `SafetyLayer`:
 1. **Sanitizer** - Detects injection patterns, escapes dangerous content
 2. **Validator** - Checks length, encoding, forbidden patterns
 3. **Policy** - Rules with severity (Critical/High/Medium/Low) and actions (Block/Warn/Review/Sanitize)
+4. **Leak Detector** - Scans for 15+ secret patterns (API keys, tokens, private keys, connection strings) at two points: tool output before it reaches the LLM, and LLM responses before they reach the user. Actions per pattern: Block (reject entirely), Redact (mask the secret), or Warn (flag but allow)
 
 Tool outputs are wrapped before reaching LLM:
 ```xml
@@ -427,6 +504,95 @@ Tool outputs are wrapped before reaching LLM:
 </tool_output>
 ```
 
+### Shell Environment Scrubbing
+
+The shell tool (`src/tools/builtin/shell.rs`) scrubs sensitive environment variables before executing commands, preventing secrets from leaking through `env`, `printenv`, or `$VAR` expansion. The sanitizer (`src/safety/sanitizer.rs`) also detects command injection patterns (chained commands, subshells, path traversal) and blocks or escapes them based on policy rules.
+
+## Skills System
+
+Skills are SKILL.md files that extend the agent's prompt with domain-specific instructions. Each skill is a YAML frontmatter block (metadata, activation criteria, required tools) followed by a markdown body that gets injected into the LLM context when the skill activates.
+
+### Trust Model
+
+| Trust Level | Source | Tool Access |
+|-------------|--------|-------------|
+| **Trusted** | User-placed in `~/.ironclaw/skills/` or workspace `skills/` | All tools available to the agent |
+| **Installed** | Downloaded from ClawHub registry | Read-only tools only (no shell, file write, HTTP) |
+
+### SKILL.md Format
+
+```yaml
+---
+name: my-skill
+version: 0.1.0
+description: Does something useful
+activation:
+  patterns:
+    - "deploy to.*production"
+  keywords:
+    - "deployment"
+  max_context_tokens: 2000
+metadata:
+  openclaw:
+    requires:
+      bins: [docker, kubectl]
+      env: [KUBECONFIG]
+---
+
+# Deployment Skill
+
+Instructions for the agent when this skill activates...
+```
+
+### Selection Pipeline
+
+1. **Gating** -- Check binary/env/config requirements; skip skills whose prerequisites are missing
+2. **Scoring** -- Deterministic scoring against message content using keywords, tags, and regex patterns
+3. **Budget** -- Select top-scoring skills that fit within `SKILLS_MAX_TOKENS` prompt budget
+4. **Attenuation** -- Apply trust-based tool ceiling; installed skills lose access to dangerous tools
+
+### Skill Tools
+
+Four built-in tools for managing skills at runtime:
+- **`skill_list`** -- List all discovered skills with trust level and status
+- **`skill_search`** -- Search ClawHub registry for available skills
+- **`skill_install`** -- Download and install a skill from ClawHub
+- **`skill_remove`** -- Remove an installed skill
+
+### Skill Directories
+
+- `~/.ironclaw/skills/` -- User's global skills (trusted)
+- `<workspace>/skills/` -- Per-workspace skills (trusted)
+- `~/.ironclaw/installed_skills/` -- Registry-installed skills (installed trust)
+
+Skills configuration: see Configuration section above.
+
+## Docker Sandbox
+
+The `src/sandbox/` module provides Docker-based isolation for job execution with a network proxy that controls outbound access and injects credentials.
+
+### Sandbox Policies
+
+| Policy | Filesystem | Network | Use Case |
+|--------|-----------|---------|----------|
+| **ReadOnly** | Read-only workspace mount | Allowlisted domains only | Analysis, code review |
+| **WorkspaceWrite** | Read-write workspace mount | Allowlisted domains only | Code generation, file edits |
+| **FullAccess** | Full filesystem | Unrestricted | Trusted admin tasks |
+
+### Network Proxy
+
+Containers route all HTTP/HTTPS traffic through a host-side proxy (`src/sandbox/proxy/`):
+- **Domain allowlist** -- Only allowlisted domains are reachable (default: package registries, docs sites, GitHub, common APIs)
+- **Credential injection** -- The `CredentialResolver` trait injects auth headers into proxied requests so secrets never enter the container environment
+- **CONNECT tunnel** -- HTTPS traffic uses CONNECT method; the proxy validates the target domain against the allowlist before establishing the tunnel
+- **Policy decisions** -- The `NetworkPolicyDecider` trait allows custom logic for allow/deny/inject decisions per request
+
+### Zero-Exposure Credential Model
+
+Secrets (API keys, tokens) are stored encrypted on the host and injected into HTTP requests by the proxy at transit time. Container processes never have access to raw credential values, preventing exfiltration even if container code is compromised.
+
+Sandbox configuration: see Configuration section above.
+
 ## Testing
 
 Tests are in `mod tests {}` blocks at the bottom of each file. Run specific module tests:
@@ -451,164 +617,13 @@ Key test patterns:
 7. **Webhook trigger endpoint** - Routines webhook trigger not yet exposed in web gateway
 8. **Full channel status view** - Gateway status widget exists, but no per-channel connection dashboard
 
-### Completed
+## Tool Architecture
 
-- ✅ **Workspace integration** - Memory tools registered, workspace passed to Agent and heartbeat
-- ✅ **WASM sandboxing** - Full implementation in `tools/wasm/` with fuel metering, memory limits, capabilities
-- ✅ **Dynamic tool building** - `tools/builder/` has LlmSoftwareBuilder with iterative build loop
-- ✅ **HTTP webhook security** - Secret validation implemented, proper error handling (no panics)
-- ✅ **Embeddings integration** - OpenAI and NEAR AI providers wired to workspace for semantic search
-- ✅ **Workspace system prompt** - Identity files (AGENTS.md, SOUL.md, USER.md, IDENTITY.md) injected into LLM context
-- ✅ **Heartbeat notifications** - Route through channel manager (broadcast API) instead of logging-only
-- ✅ **Auto-context compaction** - Triggers automatically when context exceeds threshold
-- ✅ **Embedding backfill** - Runs on startup when embeddings provider is enabled
-- ✅ **Clippy clean** - All warnings addressed via config struct refactoring
-- ✅ **Tool approval enforcement** - Tools with `requires_approval()` (shell, http, file write/patch, build_software) now gate execution, track auto-approved tools per session
-- ✅ **Tool definition refresh** - Tool definitions refreshed each iteration so newly built tools become visible in same session
-- ✅ **Worker tool call handling** - Uses `respond_with_tools()` to properly execute tool calls when `select_tools()` returns empty
-- ✅ **Gateway control plane** - Web gateway with 40+ API endpoints, SSE/WebSocket
-- ✅ **Web Control UI** - Browser-based dashboard with chat, memory, jobs, logs, extensions, routines
-- ✅ **Slack/Telegram channels** - Implemented as WASM tools
-- ✅ **Docker sandbox** - Orchestrator/worker containers with per-job auth
-- ✅ **Claude Code mode** - Delegate jobs to Claude CLI inside containers
-- ✅ **Routines system** - Cron, event, webhook, and manual triggers with guardrails
-- ✅ **Extension management** - Install, auth, activate MCP/WASM extensions via CLI and web UI
-- ✅ **libSQL/Turso backend** - Database trait abstraction (`src/db/`), feature-gated dual backend support (postgres/libsql), embedded SQLite for zero-dependency local mode
+**Keep tool-specific logic out of the main agent codebase.** The main agent provides generic infrastructure; tools are self-contained units that declare their requirements through `capabilities.json` files (API endpoints, credentials, rate limits, auth setup). Service-specific auth flows, CLI commands, and configuration do not belong in the main agent.
 
-## Adding a New Tool
+Tools can be built as **WASM** (sandboxed, credential-injected, single binary) or **MCP servers** (ecosystem of pre-built servers, any language, but no sandbox). Both are first-class via `ironclaw tool install`. Auth is declared in capabilities files with OAuth and manual token entry support.
 
-### Built-in Tools (Rust)
-
-1. Create `src/tools/builtin/my_tool.rs`
-2. Implement the `Tool` trait
-3. Add `mod my_tool;` and `pub use` in `src/tools/builtin/mod.rs`
-4. Register in `ToolRegistry::register_builtin_tools()` in `registry.rs`
-5. Add tests
-
-### WASM Tools (Recommended)
-
-WASM tools are the preferred way to add new capabilities. They run in a sandboxed environment with explicit capabilities.
-
-1. Create a new crate in `tools-src/<name>/`
-2. Implement the WIT interface (`wit/tool.wit`)
-3. Create `<name>.capabilities.json` declaring required permissions
-4. Build with `cargo build --target wasm32-wasip2 --release`
-5. Install with `ironclaw tool install path/to/tool.wasm`
-
-See `tools-src/` for examples.
-
-## Tool Architecture Principles
-
-**CRITICAL: Keep tool-specific logic out of the main agent codebase.**
-
-The main agent provides generic infrastructure; tools are self-contained units that declare their requirements through capabilities files.
-
-### What Goes in Tools (capabilities.json)
-
-- API endpoints the tool needs (HTTP allowlist)
-- Credentials required (secret names, injection locations)
-- Rate limits and timeouts
-- Auth setup instructions (see below)
-- Workspace paths the tool can read
-
-### What Does NOT Go in Main Agent
-
-- Service-specific auth flows (OAuth for Notion, Slack, etc.)
-- Service-specific CLI commands (`auth notion`, `auth slack`)
-- Service-specific configuration handling
-- Hardcoded API URLs or token formats
-
-### Tool Authentication
-
-Tools declare their auth requirements in `<tool>.capabilities.json` under the `auth` section. Two methods are supported:
-
-#### OAuth (Browser-based login)
-
-For services that support OAuth, users just click through browser login:
-
-```json
-{
-  "auth": {
-    "secret_name": "notion_api_token",
-    "display_name": "Notion",
-    "oauth": {
-      "authorization_url": "https://api.notion.com/v1/oauth/authorize",
-      "token_url": "https://api.notion.com/v1/oauth/token",
-      "client_id_env": "NOTION_OAUTH_CLIENT_ID",
-      "client_secret_env": "NOTION_OAUTH_CLIENT_SECRET",
-      "scopes": [],
-      "use_pkce": false,
-      "extra_params": { "owner": "user" }
-    },
-    "env_var": "NOTION_TOKEN"
-  }
-}
-```
-
-To enable OAuth for a tool:
-1. Register a public OAuth app with the service (e.g., notion.so/my-integrations)
-2. Configure redirect URIs: `http://localhost:9876/callback` through `http://localhost:9886/callback`
-3. Set environment variables for client_id and client_secret
-
-#### Manual Token Entry (Fallback)
-
-For services without OAuth or when OAuth isn't configured:
-
-```json
-{
-  "auth": {
-    "secret_name": "openai_api_key",
-    "display_name": "OpenAI",
-    "instructions": "Get your API key from platform.openai.com/api-keys",
-    "setup_url": "https://platform.openai.com/api-keys",
-    "token_hint": "Starts with 'sk-'",
-    "env_var": "OPENAI_API_KEY"
-  }
-}
-```
-
-#### Auth Flow Priority
-
-When running `ironclaw tool auth <tool>`:
-
-1. Check `env_var` - if set in environment, use it directly
-2. Check `oauth` - if configured, open browser for OAuth flow
-3. Fall back to `instructions` + manual token entry
-
-The agent reads auth config from the tool's capabilities file and provides the appropriate flow. No service-specific code in the main agent.
-
-### WASM Tools vs MCP Servers: When to Use Which
-
-Both are first-class in the extension system (`ironclaw tool install` handles both), but they have different strengths.
-
-**WASM Tools (IronClaw native)**
-
-- Sandboxed: fuel metering, memory limits, no access except what's allowlisted
-- Credentials injected by host runtime, tool code never sees the actual token
-- Output scanned for secret leakage before returning to the LLM
-- Auth (OAuth/manual) declared in `capabilities.json`, agent handles the flow
-- Single binary, no process management, works offline
-- Cost: must build yourself in Rust, no ecosystem, synchronous only
-
-**MCP Servers (Model Context Protocol)**
-
-- Growing ecosystem of pre-built servers (GitHub, Notion, Postgres, etc.)
-- Any language (TypeScript/Python most common)
-- Can do websockets, streaming, background polling
-- Cost: external process with full system access (no sandbox), manages own credentials, IronClaw can't prevent leaks
-
-**Decision guide:**
-
-| Scenario | Use |
-|----------|-----|
-| Good MCP server already exists | **MCP** |
-| Handles sensitive credentials (email send, banking) | **WASM** |
-| Quick prototype or one-off integration | **MCP** |
-| Core capability you'll maintain long-term | **WASM** |
-| Needs background connections (websockets, polling) | **MCP** |
-| Multiple tools share one OAuth token (e.g., Google suite) | **WASM** |
-
-The LLM-facing interface is identical for both (tool name, schema, execute), so swapping between them is transparent to the agent.
+See `src/tools/README.md` for full tool architecture, adding new tools (built-in Rust and WASM), auth JSON examples, and WASM vs MCP decision guide.
 
 ## Adding a New Channel
 
@@ -645,154 +660,15 @@ for that module's behavior. When modifying code in a module that has a spec:
 | Module | Spec File |
 |--------|-----------|
 | `src/setup/` | `src/setup/README.md` |
-
-## Code Style
-
-- Use `crate::` imports, not `super::`
-- No `pub use` re-exports unless exposing to downstream consumers
-- Prefer strong types over strings (enums, newtypes)
-- Keep functions focused, extract helpers when logic is reused
-- Comments for non-obvious logic only
-
-## Review & Fix Discipline
-
-Hard-won lessons from code review -- follow these when fixing bugs or addressing review feedback.
-
-### Fix the pattern, not just the instance
-When a reviewer flags a bug (e.g., TOCTOU race in INSERT + SELECT-back), search the entire codebase for all instances of that same pattern. A fix in `SecretsStore::create()` that doesn't also fix `WasmToolStore::store()` is half a fix.
-
-### Propagate architectural fixes to satellite types
-If a core type changes its concurrency model (e.g., `LibSqlBackend` switches to connection-per-operation), every type that was handed a resource from the old model (e.g., `LibSqlSecretsStore`, `LibSqlWasmToolStore` holding a single `Connection`) must also be updated. Grep for the old type across the codebase.
-
-### Schema translation is more than DDL
-When translating a database schema between backends (PostgreSQL to libSQL, etc.), check for:
-- **Indexes** -- diff `CREATE INDEX` statements between the two schemas
-- **Seed data** -- check for `INSERT INTO` in migrations (e.g., `leak_detection_patterns`)
-- **Semantic differences** -- document where SQL functions behave differently (e.g., `json_patch` vs `jsonb_set`)
-
-### Feature flag testing
-When adding feature-gated code, test compilation with each feature in isolation:
-```bash
-cargo check                                          # default features
-cargo check --no-default-features --features libsql  # libsql only
-cargo check --all-features                           # all features
-```
-Dead code behind the wrong `#[cfg]` gate will only show up when building with a single feature.
-
-### Mechanical verification before committing
-Run these checks on changed files before committing:
-- `grep -rnE '\.unwrap\(|\.expect\(' <files>` -- no panics in production
-- `grep -rn 'super::' <files>` -- use `crate::` imports
-- If you fixed a pattern bug, `grep` for other instances of that pattern across `src/`
+| `src/workspace/` | `src/workspace/README.md` |
+| `src/tools/` | `src/tools/README.md` |
 
 ## Workspace & Memory System
 
-Inspired by [OpenClaw](https://github.com/openclaw/openclaw), the workspace provides persistent memory for agents with a flexible filesystem-like structure.
+OpenClaw-inspired persistent memory with a flexible filesystem-like structure. Principle: "Memory is database, not RAM" -- if you want to remember something, write it explicitly. Uses hybrid search combining FTS (keyword) + vector (semantic) via Reciprocal Rank Fusion.
 
-### Key Principles
+Four memory tools for LLM use: `memory_search` (hybrid search -- call before answering questions about prior work), `memory_write`, `memory_read`, `memory_tree`. Identity files (AGENTS.md, SOUL.md, USER.md, IDENTITY.md) are injected into the LLM system prompt.
 
-1. **"Memory is database, not RAM"** - If you want to remember something, write it explicitly
-2. **Flexible structure** - Create any directory/file hierarchy you need
-3. **Self-documenting** - Use README.md files to describe directory structure
-4. **Hybrid search** - Combines FTS (keyword) + vector (semantic) via Reciprocal Rank Fusion
+The heartbeat system runs proactive periodic execution (default: 30 minutes), reading `HEARTBEAT.md` and notifying via channel if findings are detected.
 
-### Filesystem Structure
-
-```
-workspace/
-├── README.md              <- Root runbook/index
-├── MEMORY.md              <- Long-term curated memory
-├── HEARTBEAT.md           <- Periodic checklist
-├── IDENTITY.md            <- Agent name, nature, vibe
-├── SOUL.md                <- Core values
-├── AGENTS.md              <- Behavior instructions
-├── USER.md                <- User context
-├── context/               <- Identity-related docs
-│   ├── vision.md
-│   └── priorities.md
-├── daily/                 <- Daily logs
-│   ├── 2024-01-15.md
-│   └── 2024-01-16.md
-├── projects/              <- Arbitrary structure
-│   └── alpha/
-│       ├── README.md
-│       └── notes.md
-└── ...
-```
-
-### Using the Workspace
-
-```rust
-use crate::workspace::{Workspace, OpenAiEmbeddings, paths};
-
-// Create workspace for a user
-let workspace = Workspace::new("user_123", pool)
-    .with_embeddings(Arc::new(OpenAiEmbeddings::new(api_key)));
-
-// Read/write any path
-let doc = workspace.read("projects/alpha/notes.md").await?;
-workspace.write("context/priorities.md", "# Priorities\n\n1. Feature X").await?;
-workspace.append("daily/2024-01-15.md", "Completed task X").await?;
-
-// Convenience methods for well-known files
-workspace.append_memory("User prefers dark mode").await?;
-workspace.append_daily_log("Session note").await?;
-
-// List directory contents
-let entries = workspace.list("projects/").await?;
-
-// Search (hybrid FTS + vector)
-let results = workspace.search("dark mode preference", 5).await?;
-
-// Get system prompt from identity files
-let prompt = workspace.system_prompt().await?;
-```
-
-### Memory Tools
-
-Four tools for LLM use:
-
-- **`memory_search`** - Hybrid search, MUST be called before answering questions about prior work
-- **`memory_write`** - Write to any path (memory, daily_log, or custom paths)
-- **`memory_read`** - Read any file by path
-- **`memory_tree`** - View workspace structure as a tree (depth parameter, default 1)
-
-### Hybrid Search (RRF)
-
-Combines full-text search and vector similarity using Reciprocal Rank Fusion:
-
-```
-score(d) = Σ 1/(k + rank(d)) for each method where d appears
-```
-
-Default k=60. Results from both methods are combined, with documents appearing in both getting boosted scores.
-
-**Backend differences:**
-- **PostgreSQL:** `ts_rank_cd` for FTS, pgvector cosine distance for vectors, full RRF
-- **libSQL:** FTS5 for keyword search only (vector search via `libsql_vector_idx` not yet wired)
-
-### Heartbeat System
-
-Proactive periodic execution (default: 30 minutes):
-
-1. Reads `HEARTBEAT.md` checklist
-2. Runs agent turn with checklist prompt
-3. If findings, notifies via channel
-4. If nothing, agent replies "HEARTBEAT_OK" (no notification)
-
-```rust
-use crate::agent::{HeartbeatConfig, spawn_heartbeat};
-
-let config = HeartbeatConfig::default()
-    .with_interval(Duration::from_secs(60 * 30))
-    .with_notify("user_123", "telegram");
-
-spawn_heartbeat(config, workspace, llm, response_tx);
-```
-
-### Chunking Strategy
-
-Documents are chunked for search indexing:
-- Default: 800 words per chunk (roughly 800 tokens for English)
-- 15% overlap between chunks for context preservation
-- Minimum chunk size: 50 words (tiny trailing chunks merge with previous)
+See `src/workspace/README.md` for full API documentation, filesystem structure, hybrid search details, chunking strategy, and heartbeat system.

Cargo.lock

@@ -2490,7 +2490,7 @@ dependencies = [
 
 [[package]]
 name = "ironclaw"
-version = "0.4.0"
+version = "0.9.0"
 dependencies = [
  "aes-gcm",
  "aho-corasick",
@@ -2533,6 +2533,7 @@ dependencies = [
  "security-framework 3.5.1",
  "serde",
  "serde_json",
+ "serde_yml",
  "sha2",
  "subtle",
  "tempfile",
@@ -2544,6 +2545,7 @@ dependencies = [
  "tokio-stream",
  "tokio-test",
  "tokio-tungstenite 0.26.2",
+ "toml",
  "tower 0.5.3",
  "tower-http 0.6.8",
  "tracing",
@@ -2832,6 +2834,16 @@ dependencies = [
  "zerocopy 0.7.35",
 ]
 
+[[package]]
+name = "libyml"
+version = "0.0.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "3302702afa434ffa30847a83305f0a69d6abd74293b6554c18ec85c7ef30c980"
+dependencies = [
+ "anyhow",
+ "version_check",
+]
+
 [[package]]
 name = "linux-raw-sys"
 version = "0.4.15"
@@ -4591,6 +4603,21 @@ dependencies = [
  "syn 2.0.114",
 ]
 
+[[package]]
+name = "serde_yml"
+version = "0.0.12"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "59e2dd588bf1597a252c3b920e0143eb99b0f76e4e082f4c92ce34fbc9e71ddd"
+dependencies = [
+ "indexmap 2.13.0",
+ "itoa",
+ "libyml",
+ "memchr",
+ "ryu",
+ "serde",
+ "version_check",
+]
+
 [[package]]
 name = "sha1"
 version = "0.10.6"

Cargo.toml

@@ -1,14 +1,25 @@
 [workspace]
+members = ["."]
 exclude = [
+    "channels-src/discord",
     "channels-src/telegram",
     "channels-src/slack",
     "channels-src/whatsapp",
+    "tools-src/github",
     "tools-src/gmail",
+    "tools-src/google-calendar",
+    "tools-src/google-docs",
+    "tools-src/google-drive",
+    "tools-src/google-sheets",
+    "tools-src/google-slides",
+    "tools-src/okta",
+    "tools-src/slack",
+    "tools-src/telegram",
 ]
 
 [package]
 name = "ironclaw"
-version = "0.4.0"
+version = "0.9.0"
 edition = "2024"
 rust-version = "1.92"
 description = "Secure personal AI assistant that protects your data and expands its capabilities on the fly"
@@ -55,6 +66,7 @@ tracing-subscriber = { version = "0.3", features = ["env-filter", "json"] }
 
 # Configuration
 dotenvy = "0.15"
+toml = "0.8"
 
 # Core types
 uuid = { version = "1", features = ["v4", "serde"] }
@@ -76,7 +88,7 @@ termimad = "0.34"
 # Channel integrations
 axum = { version = "0.8", features = ["ws"] }
 tower = "0.5"
-tower-http = { version = "0.6", features = ["trace", "cors"] }
+tower-http = { version = "0.6", features = ["trace", "cors", "set-header"] }
 
 # Cron scheduling for routines
 cron = "0.13"
@@ -85,6 +97,9 @@ cron = "0.13"
 regex = "1"
 aho-corasick = "1"
 
+# YAML parsing for SKILL.md frontmatter
+serde_yml = "0.0.12"
+
 # Filesystem paths
 dirs = "6"
 fs4 = "0.6"
@@ -159,10 +174,6 @@ postgres = [
 libsql = ["dep:libsql"]
 integration = []
 
-[[example]]
-name = "test_heartbeat"
-required-features = ["postgres"]
-
 # The profile that 'cargo dist' will build with
 [profile.dist]
 inherits = "release"

Dockerfile.worker

@@ -21,10 +21,15 @@ RUN cargo build --release --bin ironclaw
 
 FROM debian:bookworm-slim
 
-# Install common development tools
-RUN apt-get update && apt-get install -y --no-install-recommends \
-    ca-certificates \
-    curl \
+# Install curl first (needed to fetch the GitHub CLI GPG key), then add the
+# gh CLI apt repository, then install all remaining dev tools in one layer.
+RUN apt-get update \
+    && apt-get install -y --no-install-recommends ca-certificates curl \
+    && curl -fsSL https://cli.github.com/packages/githubcli-archive-keyring.gpg \
+        | dd of=/usr/share/keyrings/githubcli-archive-keyring.gpg \
+    && echo "deb [arch=$(dpkg --print-architecture) signed-by=/usr/share/keyrings/githubcli-archive-keyring.gpg] https://cli.github.com/packages stable main" \
+        > /etc/apt/sources.list.d/github-cli.list \
+    && apt-get update && apt-get install -y --no-install-recommends \
     git \
     build-essential \
     pkg-config \
@@ -34,6 +39,7 @@ RUN apt-get update && apt-get install -y --no-install-recommends \
     python3 \
     python3-pip \
     python3-venv \
+    gh \
     && rm -rf /var/lib/apt/lists/*
 
 # Install Rust toolchain for the sandbox user

FEATURE_PARITY.md

@@ -37,7 +37,7 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Session management/routing | ✅ | ✅ | SessionManager exists |
 | Configuration hot-reload | ✅ | ❌ | |
 | Network modes (loopback/LAN/remote) | ✅ | 🚧 | HTTP only |
-| OpenAI-compatible HTTP API | ✅ | ✅ | /v1/chat/completions |
+| OpenAI-compatible HTTP API | ✅ | ✅ | /v1/chat/completions, per-request `model` override |
 | Canvas hosting | ✅ | ❌ | Agent-driven UI |
 | Gateway lock (PID-based) | ✅ | ❌ | |
 | launchd/systemd integration | ✅ | ❌ | |
@@ -45,6 +45,13 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Tailscale integration | ✅ | ❌ | |
 | Health check endpoints | ✅ | ✅ | /api/health + /api/gateway/status |
 | `doctor` diagnostics | ✅ | ❌ | |
+| Agent event broadcast | ✅ | 🚧 | SSE broadcast manager exists (SseManager) but tool/job-state events not fully wired |
+| Channel health monitor | ✅ | ❌ | Auto-restart with configurable interval |
+| Presence system | ✅ | ❌ | Beacons on connect, system presence for agents |
+| Trusted-proxy auth mode | ✅ | ❌ | Header-based auth for reverse proxies |
+| APNs push pipeline | ✅ | ❌ | Wake disconnected iOS nodes via push |
+| Oversized payload guard | ✅ | 🚧 | HTTP webhook has 64KB body limit + Content-Length check; no chat.history cap |
+| Pre-prompt context diagnostics | ✅ | ❌ | Context size logging before prompt |
 
 ### Owner: _Unassigned_
 
@@ -58,23 +65,50 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | HTTP webhook | ✅ | ✅ | - | axum with secret validation |
 | REPL (simple) | ✅ | ✅ | - | For testing |
 | WASM channels | ❌ | ✅ | - | IronClaw innovation |
-| WhatsApp | ✅ | ❌ | P1 | Baileys (Web) |
+| WhatsApp | ✅ | ❌ | P1 | Baileys (Web), same-phone mode with echo detection |
 | Telegram | ✅ | ✅ | - | WASM channel(MTProto), DM pairing, caption, /start, bot_username |
-| Discord | ✅ | ❌ | P2 | discord.js |
+| Discord | ✅ | ❌ | P2 | discord.js, thread parent binding inheritance |
 | Signal | ✅ | ❌ | P2 | signal-cli |
 | Slack | ✅ | ✅ | - | WASM tool |
-| iMessage | ✅ | ❌ | P3 | BlueBubbles recommended |
-| Feishu/Lark | ✅ | ❌ | P3 | |
+| iMessage | ✅ | ❌ | P3 | BlueBubbles or Linq recommended |
+| Linq | ✅ | ❌ | P3 | Real iMessage via API, no Mac required |
+| Feishu/Lark | ✅ | ❌ | P3 | Bitable create app/field tools |
 | LINE | ✅ | ❌ | P3 | |
 | WebChat | ✅ | ✅ | - | Web gateway chat |
 | Matrix | ✅ | ❌ | P3 | E2EE support |
-| Mattermost | ✅ | ❌ | P3 | |
+| Mattermost | ✅ | ❌ | P3 | Emoji reactions |
 | Google Chat | ✅ | ❌ | P3 | |
 | MS Teams | ✅ | ❌ | P3 | |
 | Twitch | ✅ | ❌ | P3 | |
-| Voice Call | ✅ | ❌ | P3 | Twilio/Telnyx |
+| Voice Call | ✅ | ❌ | P3 | Twilio/Telnyx, stale call reaper, pre-cached greeting |
 | Nostr | ✅ | ❌ | P3 | |
 
+### Telegram-Specific Features (since Feb 2025)
+
+| Feature | OpenClaw | IronClaw | Notes |
+|---------|----------|----------|-------|
+| Forum topic creation | ✅ | ❌ | Create topics in forum groups |
+| channel_post support | ✅ | ❌ | Bot-to-bot communication |
+| User message reactions | ✅ | ❌ | Surface inbound reactions |
+| sendPoll | ✅ | ❌ | Poll creation via agent |
+| Cron/heartbeat topic targeting | ✅ | ❌ | Messages land in correct topic |
+
+### Discord-Specific Features (since Feb 2025)
+
+| Feature | OpenClaw | IronClaw | Notes |
+|---------|----------|----------|-------|
+| Forwarded attachment downloads | ✅ | ❌ | Fetch media from forwarded messages |
+| Faster reaction state machine | ✅ | ❌ | Watchdog + debounce |
+| Thread parent binding inheritance | ✅ | ❌ | Threads inherit parent routing |
+
+### Slack-Specific Features (since Feb 2025)
+
+| Feature | OpenClaw | IronClaw | Notes |
+|---------|----------|----------|-------|
+| Streaming draft replies | ✅ | ❌ | Partial replies via draft message updates |
+| Configurable stream modes | ✅ | ❌ | Per-channel stream behavior |
+| Thread ownership | ✅ | ❌ | Thread-level ownership tracking |
+
 ### Channel Features
 
 | Feature | OpenClaw | IronClaw | Notes |
@@ -87,6 +121,9 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Thread isolation | ✅ | ✅ | Separate sessions per thread |
 | Per-channel media limits | ✅ | 🚧 | Caption support for media; no size limits |
 | Typing indicators | ✅ | 🚧 | TUI shows status |
+| Per-channel ackReaction config | ✅ | ❌ | Customizable acknowledgement reactions |
+| Group session priming | ✅ | ❌ | Member roster injected for context |
+| Sender_id in trusted metadata | ✅ | ❌ | Exposed in system metadata |
 
 ### Owner: _Unassigned_
 
@@ -104,16 +141,16 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | `config` | ✅ | ✅ | - | Read/write config |
 | `channels` | ✅ | ❌ | P2 | Channel management |
 | `models` | ✅ | 🚧 | - | Model selector in TUI |
-| `status` | ✅ | ✅ | - | System status |
+| `status` | ✅ | ✅ | - | System status (enriched session details) |
 | `agents` | ✅ | ❌ | P3 | Multi-agent management |
-| `sessions` | ✅ | ❌ | P3 | Session listing |
+| `sessions` | ✅ | ❌ | P3 | Session listing (shows subagent models) |
 | `memory` | ✅ | ✅ | - | Memory search CLI |
-| `skills` | ✅ | ❌ | P3 | Agent skills |
-| `pairing` | ✅ | ✅ | - | list/approve for channel DM pairing |
-| `nodes` | ✅ | ❌ | P3 | Device management |
+| `skills` | ✅ | ✅ | - | Skills tools + web API endpoints (install, list, activate) |
+| `pairing` | ✅ | ✅ | - | list/approve, account selector |
+| `nodes` | ✅ | ❌ | P3 | Device management, remove/clear flows |
 | `plugins` | ✅ | ❌ | P3 | Plugin management |
 | `hooks` | ✅ | ✅ | P2 | Lifecycle hooks |
-| `cron` | ✅ | ❌ | P2 | Scheduled jobs |
+| `cron` | ✅ | ❌ | P2 | Scheduled jobs (model/thinking fields in edit) |
 | `webhooks` | ✅ | ❌ | P3 | Webhook config |
 | `message send` | ✅ | ❌ | P2 | Send to channels |
 | `browser` | ✅ | ❌ | P3 | Browser automation |
@@ -122,6 +159,8 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | `logs` | ✅ | ❌ | P3 | Query logs |
 | `update` | ✅ | ❌ | P3 | Self-update |
 | `completion` | ✅ | ❌ | P3 | Shell completion |
+| `/subagents spawn` | ✅ | ❌ | P3 | Spawn subagents from chat |
+| `/export-session` | ✅ | ❌ | P3 | Export current session transcript |
 
 ### Owner: _Unassigned_
 
@@ -138,17 +177,32 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Global sessions | ✅ | ❌ | Optional shared context |
 | Session pruning | ✅ | ❌ | Auto cleanup old sessions |
 | Context compaction | ✅ | ✅ | Auto summarization |
-| Custom system prompts | ✅ | ✅ | Template variables |
-| Skills (modular capabilities) | ✅ | ❌ | Capability bundles |
+| Post-compaction read audit | ✅ | ❌ | Layer 3: workspace rules appended to summaries |
+| Post-compaction context injection | ✅ | ❌ | Workspace context as system event |
+| Custom system prompts | ✅ | ✅ | Template variables, safety guardrails |
+| Skills (modular capabilities) | ✅ | ✅ | Prompt-based skills with trust gating, attenuation, activation criteria, catalog, selector |
+| Skill routing blocks | ✅ | 🚧 | ActivationCriteria (keywords, patterns, tags) but no "Use when / Don't use when" blocks |
+| Skill path compaction | ✅ | ❌ | ~ prefix to reduce prompt tokens |
 | Thinking modes (low/med/high) | ✅ | ❌ | Configurable reasoning depth |
+| Per-model thinkingDefault override | ✅ | ❌ | Override thinking level per model |
 | Block-level streaming | ✅ | ❌ | |
 | Tool-level streaming | ✅ | ❌ | |
+| Z.AI tool_stream | ✅ | ❌ | Real-time tool call streaming |
 | Plugin tools | ✅ | ✅ | WASM tools |
 | Tool policies (allow/deny) | ✅ | ✅ | |
 | Exec approvals (`/approve`) | ✅ | ✅ | TUI approval overlay |
 | Elevated mode | ✅ | ❌ | Privileged execution |
 | Subagent support | ✅ | ✅ | Task framework |
+| `/subagents spawn` command | ✅ | ❌ | Spawn from chat |
 | Auth profiles | ✅ | ❌ | Multiple auth strategies |
+| Generic API key rotation | ✅ | ❌ | Rotate keys across providers |
+| Stuck loop detection | ✅ | ❌ | Exponential backoff on stuck agent loops |
+| llms.txt discovery | ✅ | ❌ | Auto-discover site metadata |
+| Multiple images per tool call | ✅ | ❌ | Single tool call, multiple images |
+| URL allowlist (web_search/fetch) | ✅ | ❌ | Restrict web tool targets |
+| suppressToolErrors config | ✅ | ❌ | Hide tool errors from user |
+| Intent-first tool display | ✅ | ❌ | Details and exec summaries |
+| Transcript file size in status | ✅ | ❌ | Show size in session status |
 
 ### Owner: _Unassigned_
 
@@ -159,12 +213,18 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Provider | OpenClaw | IronClaw | Priority | Notes |
 |----------|----------|----------|----------|-------|
 | NEAR AI | ✅ | ✅ | - | Primary provider |
-| Anthropic (Claude) | ✅ | 🚧 | - | Via NEAR AI proxy |
+| Anthropic (Claude) | ✅ | 🚧 | - | Via NEAR AI proxy; Opus 4.5, Sonnet 4, Sonnet 4.6 |
 | OpenAI | ✅ | 🚧 | - | Via NEAR AI proxy |
 | AWS Bedrock | ✅ | ❌ | P3 | |
 | Google Gemini | ✅ | ❌ | P3 | |
-| OpenRouter | ✅ | ❌ | P3 | |
+| NVIDIA API | ✅ | ❌ | P3 | New provider |
+| OpenRouter | ✅ | ✅ | - | Via OpenAI-compatible provider (RigAdapter) |
+| Tinfoil | ❌ | ✅ | - | Private inference provider (IronClaw-only) |
+| OpenAI-compatible | ❌ | ✅ | - | Generic OpenAI-compatible endpoint (RigAdapter) |
 | Ollama (local) | ✅ | ✅ | - | via `rig::providers::ollama` (full support) |
+| Perplexity | ✅ | ❌ | P3 | Freshness parameter for web_search |
+| MiniMax | ✅ | ❌ | P3 | Regional endpoint selection |
+| GLM-5 | ✅ | ❌ | P3 | |
 | node-llama-cpp | ✅ | ➖ | - | N/A for Rust |
 | llama.cpp (native) | ❌ | 🔮 | P3 | Rust bindings |
 
@@ -174,9 +234,11 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 |---------|----------|----------|-------|
 | Auto-discovery | ✅ | ❌ | |
 | Failover chains | ✅ | ✅ | `FailoverProvider` with configurable `fallback_model` |
-| Cooldown management | ✅ | ❌ | Skip failed providers |
+| Cooldown management | ✅ | ✅ | Lock-free per-provider cooldown in `FailoverProvider` |
 | Per-session model override | ✅ | ✅ | Model selector in TUI |
 | Model selection UI | ✅ | ✅ | TUI keyboard shortcut |
+| Per-model thinkingDefault | ✅ | ❌ | Override thinking level per model in config |
+| 1M context beta header | ✅ | ❌ | Anthropic extended context support |
 
 ### Owner: _Unassigned_
 
@@ -187,6 +249,8 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Feature | OpenClaw | IronClaw | Priority | Notes |
 |---------|----------|----------|----------|-------|
 | Image processing (Sharp) | ✅ | ❌ | P2 | Resize, format convert |
+| Configurable image resize dims | ✅ | ❌ | P2 | Per-agent dimension config |
+| Multiple images per tool call | ✅ | ❌ | P2 | Single tool invocation, multiple images |
 | Audio transcription | ✅ | ❌ | P2 | |
 | Video support | ✅ | ❌ | P3 | |
 | PDF parsing | ✅ | ❌ | P2 | pdfjs-dist |
@@ -195,6 +259,7 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Vision model integration | ✅ | ❌ | P2 | Image understanding |
 | TTS (Edge TTS) | ✅ | ❌ | P3 | Text-to-speech |
 | TTS (OpenAI) | ✅ | ❌ | P3 | |
+| Incremental TTS playback | ✅ | ❌ | P3 | iOS progressive playback |
 | Sticker-to-image | ✅ | ❌ | P3 | Telegram stickers |
 
 ### Owner: _Unassigned_
@@ -213,10 +278,13 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Auth plugins | ✅ | ❌ | |
 | Memory plugins | ✅ | ❌ | Custom backends |
 | Tool plugins | ✅ | ✅ | WASM tools |
-| Hook plugins | ✅ | ❌ | |
+| Hook plugins | ✅ | ✅ | Declarative hooks from extension capabilities |
 | Provider plugins | ✅ | ❌ | |
 | Plugin CLI (`install`, `list`) | ✅ | ✅ | `tool` subcommand |
 | ClawHub registry | ✅ | ❌ | Discovery |
+| `before_agent_start` hook | ✅ | ❌ | modelOverride/providerOverride support |
+| `before_message_write` hook | ✅ | ❌ | Pre-write message interception |
+| `llm_input`/`llm_output` hooks | ✅ | ❌ | LLM payload inspection |
 
 ### Owner: _Unassigned_
 
@@ -235,6 +303,7 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Legacy migration | ✅ | ➖ | |
 | State directory | ✅ `~/.openclaw-state/` | ✅ `~/.ironclaw/` | |
 | Credentials directory | ✅ | ✅ | Session files |
+| Full model compat fields in schema | ✅ | ❌ | pi-ai model compat exposed in config |
 
 ### Owner: _Unassigned_
 
@@ -247,16 +316,19 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Vector memory | ✅ | ✅ | pgvector |
 | Session-based memory | ✅ | ✅ | |
 | Hybrid search (BM25 + vector) | ✅ | ✅ | RRF algorithm |
+| Temporal decay (hybrid search) | ✅ | ❌ | Opt-in time-based scoring factor |
+| MMR re-ranking | ✅ | ❌ | Maximal marginal relevance for result diversity |
+| LLM-based query expansion | ✅ | ❌ | Expand FTS queries via LLM |
 | OpenAI embeddings | ✅ | ✅ | |
 | Gemini embeddings | ✅ | ❌ | |
 | Local embeddings | ✅ | ❌ | |
 | SQLite-vec backend | ✅ | ❌ | IronClaw uses PostgreSQL |
-| LanceDB backend | ✅ | ❌ | |
+| LanceDB backend | ✅ | ❌ | Configurable auto-capture max length |
 | QMD backend | ✅ | ❌ | |
 | Atomic reindexing | ✅ | ✅ | |
-| Embeddings batching | ✅ | ❌ | |
+| Embeddings batching | ✅ | ✅ | `embed_batch` on EmbeddingProvider trait |
 | Citation support | ✅ | ❌ | |
-| Memory CLI commands | ✅ | ❌ | `memory search/index/status` |
+| Memory CLI commands | ✅ | ✅ | `memory search/read/write/tree/status` CLI subcommands |
 | Flexible path structure | ✅ | ✅ | Filesystem-like API |
 | Identity files (AGENTS.md, etc.) | ✅ | ✅ | |
 | Daily logs | ✅ | ✅ | |
@@ -272,12 +344,16 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 |---------|----------|----------|----------|-------|
 | iOS app (SwiftUI) | ✅ | 🚫 | - | Out of scope initially |
 | Android app (Kotlin) | ✅ | 🚫 | - | Out of scope initially |
+| Apple Watch companion | ✅ | 🚫 | - | Send/receive messages MVP |
 | Gateway WebSocket client | ✅ | 🚫 | - | |
 | Camera/photo access | ✅ | 🚫 | - | |
 | Voice input | ✅ | 🚫 | - | |
 | Push-to-talk | ✅ | 🚫 | - | |
 | Location sharing | ✅ | 🚫 | - | |
 | Node pairing | ✅ | 🚫 | - | |
+| APNs push notifications | ✅ | 🚫 | - | Wake disconnected nodes before invoke |
+| Share to OpenClaw (iOS) | ✅ | 🚫 | - | iOS share sheet integration |
+| Background listening toggle | ✅ | 🚫 | - | iOS background audio |
 
 ### Owner: _Unassigned_ (if ever prioritized)
 
@@ -288,12 +364,17 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Feature | OpenClaw | IronClaw | Priority | Notes |
 |---------|----------|----------|----------|-------|
 | SwiftUI native app | ✅ | 🚫 | - | Out of scope |
-| Menu bar presence | ✅ | 🚫 | - | |
+| Menu bar presence | ✅ | 🚫 | - | Animated menubar icon |
 | Bundled gateway | ✅ | 🚫 | - | |
-| Canvas hosting | ✅ | 🚫 | - | |
-| Voice wake | ✅ | 🚫 | - | |
+| Canvas hosting | ✅ | 🚫 | - | Agent-controlled panel with placement/resizing |
+| Voice wake | ✅ | 🚫 | - | Overlay, mic picker, language selection, live meter |
+| Voice wake overlay | ✅ | 🚫 | - | Partial transcripts, adaptive delays, dismiss animations |
+| Push-to-talk hotkey | ✅ | 🚫 | - | System-wide hotkey |
 | Exec approval dialogs | ✅ | ✅ | - | TUI overlay |
 | iMessage integration | ✅ | 🚫 | - | |
+| Instances tab | ✅ | 🚫 | - | Presence beacons across instances |
+| Agent events debug window | ✅ | 🚫 | - | Real-time event inspector |
+| Sparkle auto-updates | ✅ | 🚫 | - | Appcast distribution |
 
 ### Owner: _Unassigned_ (if ever prioritized)
 
@@ -310,7 +391,10 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Config editing | ✅ | ❌ | P3 | |
 | Debug/logs viewer | ✅ | ✅ | - | Real-time log streaming with level/target filters |
 | WebChat interface | ✅ | ✅ | - | Web gateway chat with SSE/WebSocket |
-| Canvas system (A2UI) | ✅ | ❌ | P3 | Agent-driven UI |
+| Canvas system (A2UI) | ✅ | ❌ | P3 | Agent-driven UI, improved asset resolution |
+| Control UI i18n | ✅ | ❌ | P3 | English, Chinese, Portuguese |
+| WebChat theme sync | ✅ | ❌ | P3 | Sync with system dark/light mode |
+| Partial output on abort | ✅ | ❌ | P2 | Preserve partial output when aborting |
 
 ### Owner: _Unassigned_
 
@@ -321,20 +405,26 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Feature | OpenClaw | IronClaw | Priority | Notes |
 |---------|----------|----------|----------|-------|
 | Cron jobs | ✅ | ✅ | - | Routines with cron trigger |
+| Cron stagger controls | ✅ | ❌ | P3 | Default stagger for scheduled jobs |
+| Cron finished-run webhook | ✅ | ❌ | P3 | Webhook on job completion |
 | Timezone support | ✅ | ✅ | - | Via cron expressions |
 | One-shot/recurring jobs | ✅ | ✅ | - | Manual + cron triggers |
+| Channel health monitor | ✅ | ❌ | P2 | Auto-restart with configurable interval |
 | `beforeInbound` hook | ✅ | ✅ | P2 | |
 | `beforeOutbound` hook | ✅ | ✅ | P2 | |
 | `beforeToolCall` hook | ✅ | ✅ | P2 | |
+| `before_agent_start` hook | ✅ | ❌ | P2 | Model/provider override |
+| `before_message_write` hook | ✅ | ❌ | P2 | Pre-write interception |
 | `onMessage` hook | ✅ | ✅ | - | Routines with event trigger |
 | `onSessionStart` hook | ✅ | ✅ | P2 | |
 | `onSessionEnd` hook | ✅ | ✅ | P2 | |
 | `transcribeAudio` hook | ✅ | ❌ | P3 | |
 | `transformResponse` hook | ✅ | ✅ | P2 | |
-| Bundled hooks | ✅ | ❌ | P2 | |
-| Plugin hooks | ✅ | ❌ | P3 | |
-| Workspace hooks | ✅ | ❌ | P2 | Inline code |
-| Outbound webhooks | ✅ | ❌ | P2 | |
+| `llm_input`/`llm_output` hooks | ✅ | ❌ | P3 | LLM payload inspection |
+| Bundled hooks | ✅ | ✅ | P2 | Audit + declarative rule/webhook hooks |
+| Plugin hooks | ✅ | ✅ | P3 | Registered from WASM `capabilities.json` |
+| Workspace hooks | ✅ | ✅ | P2 | `hooks/hooks.json` and `hooks/*.hook.json` |
+| Outbound webhooks | ✅ | ✅ | P2 | Fire-and-forget lifecycle event delivery |
 | Heartbeat system | ✅ | ✅ | - | Periodic execution |
 | Gmail pub/sub | ✅ | ❌ | P3 | |
 
@@ -349,6 +439,7 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Gateway token auth | ✅ | ✅ | Bearer token auth on web gateway |
 | Device pairing | ✅ | ❌ | |
 | Tailscale identity | ✅ | ❌ | |
+| Trusted-proxy auth | ✅ | ❌ | Header-based reverse proxy auth |
 | OAuth flows | ✅ | 🚧 | NEAR AI OAuth |
 | DM pairing verification | ✅ | ✅ | ironclaw pairing approve, host APIs |
 | Allowlist/blocklist | ✅ | 🚧 | allow_from + pairing store |
@@ -356,18 +447,26 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Exec approvals | ✅ | ✅ | TUI overlay |
 | TLS 1.3 minimum | ✅ | ✅ | reqwest rustls |
 | SSRF protection | ✅ | ✅ | WASM allowlist |
+| SSRF IPv6 transition bypass block | ✅ | ❌ | Block IPv4-mapped IPv6 bypasses |
+| Cron webhook SSRF guard | ✅ | ❌ | SSRF checks on webhook delivery |
 | Loopback-first | ✅ | 🚧 | HTTP binds 0.0.0.0 |
 | Docker sandbox | ✅ | ✅ | Orchestrator/worker containers |
+| Podman support | ✅ | ❌ | Alternative to Docker |
 | WASM sandbox | ❌ | ✅ | IronClaw innovation |
+| Sandbox env sanitization | ✅ | 🚧 | Shell tool scrubs env vars (secret detection); docker container env sanitization partial |
 | Tool policies | ✅ | ✅ | |
 | Elevated mode | ✅ | ❌ | |
-| Safe bins allowlist | ✅ | ❌ | |
+| Safe bins allowlist | ✅ | ❌ | Hardened path trust |
 | LD*/DYLD* validation | ✅ | ❌ | |
-| Path traversal prevention | ✅ | ✅ | |
+| Path traversal prevention | ✅ | ✅ | Including config includes (OC-06) |
+| Credential theft via env injection | ✅ | 🚧 | Shell env scrubbing + command injection detection; no full OC-09 defense |
+| Session file permissions (0o600) | ✅ | ✅ | Session token file set to 0o600 in llm/session.rs |
+| Skill download path restriction | ✅ | ❌ | Prevent arbitrary write targets |
 | Webhook signature verification | ✅ | ✅ | |
 | Media URL validation | ✅ | ❌ | |
 | Prompt injection defense | ✅ | ✅ | Pattern detection, sanitization |
 | Leak detection | ✅ | ✅ | Secret exfiltration |
+| Dangerous tool re-enable warning | ✅ | ❌ | Warn when gateway.tools.allow re-enables HTTP tools |
 
 ### Owner: _Unassigned_
 
@@ -387,6 +486,9 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Coverage | V8 | tarpaulin/llvm-cov | |
 | CI/CD | GitHub Actions | GitHub Actions | |
 | Pre-commit hooks | prek | - | Consider adding |
+| Docker: Chromium + Xvfb | ✅ | ❌ | Optional browser in container |
+| Docker: init scripts | ✅ | ❌ | /openclaw-init.d/ support |
+| Browser: extraArgs config | ✅ | ❌ | Custom Chrome launch arguments |
 
 ### Owner: _Unassigned_
 
@@ -399,7 +501,7 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 - ✅ HTTP webhook channel
 - ✅ DM pairing (ironclaw pairing list/approve, host APIs)
 - ✅ WASM tool sandbox
-- ✅ Workspace/memory with hybrid search
+- ✅ Workspace/memory with hybrid search + embeddings batching
 - ✅ Prompt injection defense
 - ✅ Heartbeat system
 - ✅ Session management
@@ -414,19 +516,27 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 - ✅ Cron job scheduling (routines)
 - ✅ CLI subcommands (onboard, config, status, memory)
 - ✅ Gateway token auth
+- ✅ Skills system (prompt-based with trust gating, attenuation, activation criteria)
+- ✅ Session file permissions (0o600)
+- ✅ Memory CLI commands (search, read, write, tree, status)
+- ✅ Shell env scrubbing + command injection detection
+- ✅ Tinfoil private inference provider
+- ✅ OpenAI-compatible / OpenRouter provider support
 
 ### P1 - High Priority
 - ❌ Slack channel (real implementation)
 - ✅ Telegram channel (WASM, DM pairing, caption, /start)
 - ❌ WhatsApp channel
 - ✅ Multi-provider failover (`FailoverProvider` with retryable error classification)
-- ✅ Hooks system (beforeInbound, beforeToolCall, beforeOutbound, onSessionStart, onSessionEnd, transformResponse)
+- ✅ Hooks system (core lifecycle hooks + bundled/plugin/workspace hooks + outbound webhooks)
 
 ### P2 - Medium Priority
 - ❌ Media handling (images, PDFs)
-- ❌ Ollama/local model support
+- ✅ Ollama/local model support (via rig::providers::ollama)
 - ❌ Configuration hot-reload
 - ❌ Webhook trigger endpoint in web gateway
+- ❌ Channel health monitor with auto-restart
+- ❌ Partial output preservation on abort
 
 ### P3 - Lower Priority
 - ❌ Discord channel
@@ -435,8 +545,12 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 - ❌ Other messaging platforms
 - ❌ TTS/audio features
 - ❌ Video support
-- ❌ Skills system
+- 🚧 Skills routing blocks (activation criteria exist, but no "Use when / Don't use when")
 - ❌ Plugin registry
+- ❌ Streaming (block/tool/Z.AI tool_stream)
+- ❌ Memory: temporal decay, MMR re-ranking, query expansion
+- ❌ Control UI i18n
+- ❌ Stuck loop detection
 
 ---
 
@@ -461,9 +575,12 @@ IronClaw intentionally differs from OpenClaw in these ways:
 
 1. **Rust vs TypeScript**: Native performance, memory safety, single binary distribution
 2. **WASM sandbox vs Docker**: Lighter weight, faster startup, capability-based security
-3. **PostgreSQL vs SQLite**: Better suited for production deployments
+3. **PostgreSQL + libSQL vs SQLite**: Dual-backend (production PG + embedded libSQL for zero-dep local mode)
 4. **NEAR AI focus**: Primary provider with session-based auth
 5. **No mobile/desktop apps**: Focus on server-side and CLI initially
 6. **WASM channels**: Novel extension mechanism not in OpenClaw
+7. **Tinfoil private inference**: IronClaw-only provider for private/encrypted inference
+8. **GitHub WASM tool**: Native GitHub integration as WASM tool
+9. **Prompt-based skills**: Different approach than OpenClaw capability bundles (trust gating, attenuation)
 
 These are intentional architectural choices, not gaps to be filled.

README.md

@@ -139,8 +139,9 @@ ironclaw onboard
 ```
 
 The wizard handles database connection, NEAR AI authentication (via browser OAuth),
-and secrets encryption (using your system keychain). All settings are saved to
-`~/.ironclaw/settings.toml`.
+and secrets encryption (using your system keychain). Settings are persisted in the
+connected database; bootstrap variables (e.g. `DATABASE_URL`, `LLM_BACKEND`) are
+written to `~/.ironclaw/.env` so they are available before the database connects.
 
 ## Security
 

channels-src/discord/Cargo.toml

@@ -21,3 +21,5 @@ lto = true
 codegen-units = 1
 
 
+
+[workspace]

channels-src/slack/Cargo.toml

@@ -27,3 +27,5 @@ opt-level = "s"
 lto = true
 strip = true
 codegen-units = 1
+
+[workspace]

channels-src/telegram/Cargo.toml

@@ -16,9 +16,14 @@ wit-bindgen = "0.36"
 serde = { version = "1.0", features = ["derive"] }
 serde_json = "1.0"
 
+# Exclude from parent workspace (this is a standalone WASM component)
+[workspace]
+
 [profile.release]
 # Optimize for size
 opt-level = "s"
 lto = true
 strip = true
 codegen-units = 1
+
+[workspace]

channels-src/telegram/src/lib.rs

@@ -1038,9 +1038,18 @@ fn handle_message(message: TelegramMessage) {
         },
     );
 
-    // For /start with no args, emit placeholder so agent can respond with welcome
-    let content_to_emit = if cleaned_text.is_empty() && content.trim().starts_with('/') {
+    // Determine what to emit to the agent.
+    // - `/start` (no args): emit a welcome placeholder so the agent greets the user
+    // - Other bare `/commands` (e.g. /interrupt, /help): pass the raw command through
+    //   so Submission::parse() can handle it
+    // - Commands with args (e.g. `/start hello`): cleaned_text already has the args
+    // - Plain text: pass through as-is
+    let trimmed_content = content.trim();
+    let content_to_emit = if trimmed_content.eq_ignore_ascii_case("/start") {
         "[User started the bot]".to_string()
+    } else if cleaned_text.is_empty() && trimmed_content.starts_with('/') {
+        // Bare control command like /interrupt, /stop, /help — pass through raw
+        trimmed_content.to_string()
     } else if cleaned_text.is_empty() {
         return;
     } else {
@@ -1159,6 +1168,77 @@ mod tests {
         assert_eq!(clean_message_text("@MyBot", Some("MyBot")), "");
     }
 
+    #[test]
+    fn test_clean_message_text_bare_commands() {
+        // Bare commands return empty (the caller decides what to emit)
+        assert_eq!(clean_message_text("/start", None), "");
+        assert_eq!(clean_message_text("/interrupt", None), "");
+        assert_eq!(clean_message_text("/stop", None), "");
+        assert_eq!(clean_message_text("/help", None), "");
+        assert_eq!(clean_message_text("/undo", None), "");
+        assert_eq!(clean_message_text("/ping", None), "");
+
+        // Commands with args: command prefix stripped, args returned
+        assert_eq!(clean_message_text("/start hello", None), "hello");
+        assert_eq!(clean_message_text("/help me please", None), "me please");
+        assert_eq!(clean_message_text("/model claude-opus-4-6", None), "claude-opus-4-6");
+    }
+
+    /// Tests for the content_to_emit logic in handle_message.
+    /// Since handle_message uses WASM host calls, we test the decision logic inline.
+    #[test]
+    fn test_content_to_emit_logic() {
+        // Simulates the content_to_emit decision for various inputs.
+        // This mirrors the logic in handle_message after clean_message_text.
+        fn resolve_content(content: &str) -> Option<String> {
+            let cleaned_text = clean_message_text(content, None);
+            let trimmed_content = content.trim();
+            if trimmed_content.eq_ignore_ascii_case("/start") {
+                Some("[User started the bot]".to_string())
+            } else if cleaned_text.is_empty() && trimmed_content.starts_with('/') {
+                Some(trimmed_content.to_string())
+            } else if cleaned_text.is_empty() {
+                None // would return/skip in handle_message
+            } else {
+                Some(cleaned_text)
+            }
+        }
+
+        // /start → welcome placeholder
+        assert_eq!(resolve_content("/start"), Some("[User started the bot]".to_string()));
+        assert_eq!(resolve_content("/Start"), Some("[User started the bot]".to_string()));
+        assert_eq!(resolve_content("  /start  "), Some("[User started the bot]".to_string()));
+
+        // /start with args → pass args through
+        assert_eq!(resolve_content("/start hello"), Some("hello".to_string()));
+
+        // Control commands → pass through raw so Submission::parse() can match
+        assert_eq!(resolve_content("/interrupt"), Some("/interrupt".to_string()));
+        assert_eq!(resolve_content("/stop"), Some("/stop".to_string()));
+        assert_eq!(resolve_content("/help"), Some("/help".to_string()));
+        assert_eq!(resolve_content("/undo"), Some("/undo".to_string()));
+        assert_eq!(resolve_content("/redo"), Some("/redo".to_string()));
+        assert_eq!(resolve_content("/ping"), Some("/ping".to_string()));
+        assert_eq!(resolve_content("/tools"), Some("/tools".to_string()));
+        assert_eq!(resolve_content("/compact"), Some("/compact".to_string()));
+        assert_eq!(resolve_content("/clear"), Some("/clear".to_string()));
+        assert_eq!(resolve_content("/version"), Some("/version".to_string()));
+
+        // Commands with args → cleaned text (command stripped)
+        assert_eq!(resolve_content("/help me please"), Some("me please".to_string()));
+
+        // Plain text → pass through
+        assert_eq!(resolve_content("hello world"), Some("hello world".to_string()));
+        assert_eq!(resolve_content("just text"), Some("just text".to_string()));
+
+        // Empty / whitespace → skip (None)
+        assert_eq!(resolve_content(""), None);
+        assert_eq!(resolve_content("   "), None);
+
+        // Bare @mention without bot → skip
+        assert_eq!(resolve_content("@botname"), None);
+    }
+
     #[test]
     fn test_config_with_owner_id() {
         let json = r#"{"owner_id": 123456789}"#;

channels-src/whatsapp/Cargo.toml

@@ -16,3 +16,5 @@ serde_json = "1"
 opt-level = "s"
 lto = true
 strip = true
+
+[workspace]

deploy/env.example

@@ -2,12 +2,15 @@
 # Do not use placeholder passwords in production.
 DATABASE_URL=postgres://ironclaw:CHANGE_ME@localhost:5432/ironclaw
 
-# NEAR AI
-NEARAI_SESSION_TOKEN=CHANGE_ME
+# NEAR AI Cloud (API key auth, Chat Completions API)
+# Get an API key from https://cloud.near.ai
+NEARAI_API_KEY=CHANGE_ME
 NEARAI_MODEL=claude-3-5-sonnet-20241022
 NEARAI_BASE_URL=https://cloud-api.near.ai
-NEARAI_AUTH_URL=https://private.near.ai
-NEARAI_API_MODE=chat_completions
+
+# Or use NEAR AI Chat (session token auth, Responses API):
+# NEARAI_SESSION_TOKEN=sess_...
+# NEARAI_BASE_URL=https://private.near.ai
 
 # Agent
 AGENT_NAME=ironclaw

migrations/V9__flexible_embedding_dimension.sql

@@ -0,0 +1,43 @@
+-- Allow embedding vectors of any dimension (not just 1536).
+-- This supports Ollama models (768-dim nomic-embed-text, 1024-dim mxbai-embed-large)
+-- alongside OpenAI models (1536-dim text-embedding-3-small, 3072-dim text-embedding-3-large).
+--
+-- NOTE: HNSW indexes require a fixed dimension, so we drop the index.
+-- Exact (sequential) cosine distance search still works without the index.
+-- For a personal assistant workspace the dataset is small enough that this
+-- has negligible impact on query latency.
+
+-- Drop dependent views first
+DROP VIEW IF EXISTS chunks_pending_embedding;
+DROP VIEW IF EXISTS memory_documents_summary;
+
+DROP INDEX IF EXISTS idx_memory_chunks_embedding;
+
+ALTER TABLE memory_chunks
+    ALTER COLUMN embedding TYPE vector
+    USING embedding::vector;
+
+-- Recreate the views
+CREATE VIEW memory_documents_summary AS
+SELECT
+    d.id,
+    d.user_id,
+    d.path,
+    d.created_at,
+    d.updated_at,
+    COUNT(c.id) as chunk_count,
+    COUNT(c.embedding) as embedded_chunk_count
+FROM memory_documents d
+LEFT JOIN memory_chunks c ON c.document_id = d.id
+GROUP BY d.id;
+
+CREATE VIEW chunks_pending_embedding AS
+SELECT
+    c.id as chunk_id,
+    c.document_id,
+    d.user_id,
+    d.path,
+    LENGTH(c.content) as content_length
+FROM memory_chunks c
+JOIN memory_documents d ON d.id = c.document_id
+WHERE c.embedding IS NULL;

registry/_bundles.json

@@ -0,0 +1,42 @@
+{
+  "bundles": {
+    "google": {
+      "display_name": "Google Suite",
+      "description": "Gmail, Calendar, Drive, Docs, Sheets, Slides",
+      "extensions": [
+        "tools/gmail",
+        "tools/google-calendar",
+        "tools/google-docs",
+        "tools/google-drive",
+        "tools/google-sheets",
+        "tools/google-slides"
+      ],
+      "shared_auth": "google_oauth_token"
+    },
+    "messaging": {
+      "display_name": "Messaging Channels",
+      "description": "Discord, Telegram, Slack, and WhatsApp channels",
+      "extensions": [
+        "channels/discord",
+        "channels/telegram",
+        "channels/slack",
+        "channels/whatsapp"
+      ],
+      "shared_auth": null
+    },
+    "default": {
+      "display_name": "Recommended Set",
+      "description": "Core tools and channels for a productive setup",
+      "extensions": [
+        "tools/github",
+        "tools/gmail",
+        "tools/google-calendar",
+        "tools/google-drive",
+        "tools/slack",
+        "channels/telegram",
+        "channels/slack"
+      ],
+      "shared_auth": null
+    }
+  }
+}

registry/channels/discord.json

@@ -0,0 +1,31 @@
+{
+  "name": "discord",
+  "display_name": "Discord",
+  "kind": "channel",
+  "version": "0.1.0",
+  "description": "Discord Gateway/Webhook channel for slash commands, buttons, and messages",
+  "keywords": ["messaging", "chat", "discord", "bot"],
+
+  "source": {
+    "dir": "channels-src/discord",
+    "capabilities": "discord.capabilities.json",
+    "crate_name": "discord-channel"
+  },
+
+  "artifacts": {
+    "wasm32-wasip2": {
+      "url": null,
+      "sha256": null
+    }
+  },
+
+  "auth_summary": {
+    "method": "manual",
+    "provider": "Discord",
+    "secrets": ["discord_bot_token"],
+    "shared_auth": null,
+    "setup_url": "https://discord.com/developers/applications"
+  },
+
+  "tags": ["messaging"]
+}

registry/channels/slack.json

@@ -0,0 +1,31 @@
+{
+  "name": "slack",
+  "display_name": "Slack",
+  "kind": "channel",
+  "version": "0.1.0",
+  "description": "Slack Events API channel for receiving and responding to Slack messages",
+  "keywords": ["messaging", "chat", "workspace", "slack"],
+
+  "source": {
+    "dir": "channels-src/slack",
+    "capabilities": "slack.capabilities.json",
+    "crate_name": "slack-channel"
+  },
+
+  "artifacts": {
+    "wasm32-wasip2": {
+      "url": null,
+      "sha256": null
+    }
+  },
+
+  "auth_summary": {
+    "method": "manual",
+    "provider": "Slack",
+    "secrets": ["slack_bot_token", "slack_signing_secret"],
+    "shared_auth": null,
+    "setup_url": "https://api.slack.com/apps"
+  },
+
+  "tags": ["default", "messaging"]
+}

registry/channels/telegram.json

@@ -0,0 +1,31 @@
+{
+  "name": "telegram",
+  "display_name": "Telegram",
+  "kind": "channel",
+  "version": "0.1.0",
+  "description": "Telegram Bot API channel for receiving and responding to messages",
+  "keywords": ["messaging", "bot", "chat", "telegram"],
+
+  "source": {
+    "dir": "channels-src/telegram",
+    "capabilities": "telegram.capabilities.json",
+    "crate_name": "telegram-channel"
+  },
+
+  "artifacts": {
+    "wasm32-wasip2": {
+      "url": null,
+      "sha256": null
+    }
+  },
+
+  "auth_summary": {
+    "method": "manual",
+    "provider": "Telegram",
+    "secrets": ["telegram_bot_token"],
+    "shared_auth": null,
+    "setup_url": "https://t.me/BotFather"
+  },
+
+  "tags": ["default", "messaging"]
+}

registry/channels/whatsapp.json

@@ -0,0 +1,31 @@
+{
+  "name": "whatsapp",
+  "display_name": "WhatsApp",
+  "kind": "channel",
+  "version": "0.1.0",
+  "description": "WhatsApp Cloud API channel for receiving and responding to messages",
+  "keywords": ["messaging", "chat", "whatsapp", "meta"],
+
+  "source": {
+    "dir": "channels-src/whatsapp",
+    "capabilities": "whatsapp.capabilities.json",
+    "crate_name": "whatsapp-channel"
+  },
+
+  "artifacts": {
+    "wasm32-wasip2": {
+      "url": null,
+      "sha256": null
+    }
+  },
+
+  "auth_summary": {
+    "method": "manual",
+    "provider": "Meta",
+    "secrets": ["whatsapp_access_token", "whatsapp_verify_token"],
+    "shared_auth": null,
+    "setup_url": "https://developers.facebook.com/apps/"
+  },
+
+  "tags": ["messaging"]
+}

registry/tools/github.json

@@ -0,0 +1,31 @@
+{
+  "name": "github",
+  "display_name": "GitHub",
+  "kind": "tool",
+  "version": "0.1.0",
+  "description": "GitHub integration for issues, PRs, repos, and code search",
+  "keywords": ["git", "code", "issues", "pull-requests", "repositories"],
+
+  "source": {
+    "dir": "tools-src/github",
+    "capabilities": "github-tool.capabilities.json",
+    "crate_name": "github-tool"
+  },
+
+  "artifacts": {
+    "wasm32-wasip2": {
+      "url": null,
+      "sha256": null
+    }
+  },
+
+  "auth_summary": {
+    "method": "manual",
+    "provider": "GitHub",
+    "secrets": ["github_token"],
+    "shared_auth": null,
+    "setup_url": "https://github.com/settings/tokens"
+  },
+
+  "tags": ["default", "development"]
+}

registry/tools/gmail.json

@@ -0,0 +1,31 @@
+{
+  "name": "gmail",
+  "display_name": "Gmail",
+  "kind": "tool",
+  "version": "0.1.0",
+  "description": "Read, send, and manage Gmail messages and threads",
+  "keywords": ["email", "google", "mail", "messaging"],
+
+  "source": {
+    "dir": "tools-src/gmail",
+    "capabilities": "gmail-tool.capabilities.json",
+    "crate_name": "gmail-tool"
+  },
+
+  "artifacts": {
+    "wasm32-wasip2": {
+      "url": null,
+      "sha256": null
+    }
+  },
+
+  "auth_summary": {
+    "method": "oauth",
+    "provider": "Google",
+    "secrets": ["google_oauth_token"],
+    "shared_auth": "google_oauth_token",
+    "setup_url": "https://console.cloud.google.com/apis/credentials"
+  },
+
+  "tags": ["default", "google", "messaging"]
+}

registry/tools/google-calendar.json

@@ -0,0 +1,31 @@
+{
+  "name": "google-calendar",
+  "display_name": "Google Calendar",
+  "kind": "tool",
+  "version": "0.1.0",
+  "description": "Create, read, update, and delete Google Calendar events",
+  "keywords": ["calendar", "google", "scheduling", "events"],
+
+  "source": {
+    "dir": "tools-src/google-calendar",
+    "capabilities": "google-calendar-tool.capabilities.json",
+    "crate_name": "google-calendar-tool"
+  },
+
+  "artifacts": {
+    "wasm32-wasip2": {
+      "url": null,
+      "sha256": null
+    }
+  },
+
+  "auth_summary": {
+    "method": "oauth",
+    "provider": "Google",
+    "secrets": ["google_oauth_token"],
+    "shared_auth": "google_oauth_token",
+    "setup_url": "https://console.cloud.google.com/apis/credentials"
+  },
+
+  "tags": ["default", "google", "productivity"]
+}

registry/tools/google-docs.json

@@ -0,0 +1,31 @@
+{
+  "name": "google-docs",
+  "display_name": "Google Docs",
+  "kind": "tool",
+  "version": "0.1.0",
+  "description": "Create and edit Google Docs documents",
+  "keywords": ["documents", "google", "writing", "docs"],
+
+  "source": {
+    "dir": "tools-src/google-docs",
+    "capabilities": "google-docs-tool.capabilities.json",
+    "crate_name": "google-docs-tool"
+  },
+
+  "artifacts": {
+    "wasm32-wasip2": {
+      "url": null,
+      "sha256": null
+    }
+  },
+
+  "auth_summary": {
+    "method": "oauth",
+    "provider": "Google",
+    "secrets": ["google_oauth_token"],
+    "shared_auth": "google_oauth_token",
+    "setup_url": "https://console.cloud.google.com/apis/credentials"
+  },
+
+  "tags": ["google", "productivity"]
+}

registry/tools/google-drive.json

@@ -0,0 +1,31 @@
+{
+  "name": "google-drive",
+  "display_name": "Google Drive",
+  "kind": "tool",
+  "version": "0.1.0",
+  "description": "Upload, download, search, and manage Google Drive files and folders",
+  "keywords": ["storage", "google", "files", "drive"],
+
+  "source": {
+    "dir": "tools-src/google-drive",
+    "capabilities": "google-drive-tool.capabilities.json",
+    "crate_name": "google-drive-tool"
+  },
+
+  "artifacts": {
+    "wasm32-wasip2": {
+      "url": null,
+      "sha256": null
+    }
+  },
+
+  "auth_summary": {
+    "method": "oauth",
+    "provider": "Google",
+    "secrets": ["google_oauth_token"],
+    "shared_auth": "google_oauth_token",
+    "setup_url": "https://console.cloud.google.com/apis/credentials"
+  },
+
+  "tags": ["default", "google", "storage"]
+}

registry/tools/google-sheets.json

@@ -0,0 +1,31 @@
+{
+  "name": "google-sheets",
+  "display_name": "Google Sheets",
+  "kind": "tool",
+  "version": "0.1.0",
+  "description": "Read and write Google Sheets spreadsheet data",
+  "keywords": ["spreadsheets", "google", "data", "sheets"],
+
+  "source": {
+    "dir": "tools-src/google-sheets",
+    "capabilities": "google-sheets-tool.capabilities.json",
+    "crate_name": "google-sheets-tool"
+  },
+
+  "artifacts": {
+    "wasm32-wasip2": {
+      "url": null,
+      "sha256": null
+    }
+  },
+
+  "auth_summary": {
+    "method": "oauth",
+    "provider": "Google",
+    "secrets": ["google_oauth_token"],
+    "shared_auth": "google_oauth_token",
+    "setup_url": "https://console.cloud.google.com/apis/credentials"
+  },
+
+  "tags": ["google", "productivity"]
+}

registry/tools/google-slides.json

@@ -0,0 +1,31 @@
+{
+  "name": "google-slides",
+  "display_name": "Google Slides",
+  "kind": "tool",
+  "version": "0.1.0",
+  "description": "Create and edit Google Slides presentations",
+  "keywords": ["presentations", "google", "slides"],
+
+  "source": {
+    "dir": "tools-src/google-slides",
+    "capabilities": "google-slides-tool.capabilities.json",
+    "crate_name": "google-slides-tool"
+  },
+
+  "artifacts": {
+    "wasm32-wasip2": {
+      "url": null,
+      "sha256": null
+    }
+  },
+
+  "auth_summary": {
+    "method": "oauth",
+    "provider": "Google",
+    "secrets": ["google_oauth_token"],
+    "shared_auth": "google_oauth_token",
+    "setup_url": "https://console.cloud.google.com/apis/credentials"
+  },
+
+  "tags": ["google", "productivity"]
+}

registry/tools/okta.json

@@ -0,0 +1,31 @@
+{
+  "name": "okta",
+  "display_name": "Okta",
+  "kind": "tool",
+  "version": "0.1.0",
+  "description": "Okta SSO for user profile, app catalog, and SSO launch links",
+  "keywords": ["sso", "identity", "authentication", "okta"],
+
+  "source": {
+    "dir": "tools-src/okta",
+    "capabilities": "okta-tool.capabilities.json",
+    "crate_name": "okta-tool"
+  },
+
+  "artifacts": {
+    "wasm32-wasip2": {
+      "url": null,
+      "sha256": null
+    }
+  },
+
+  "auth_summary": {
+    "method": "oauth",
+    "provider": "Okta",
+    "secrets": ["okta_oauth_token"],
+    "shared_auth": null,
+    "setup_url": "https://developer.okta.com/docs/guides/implement-oauth-for-okta/main/"
+  },
+
+  "tags": ["identity"]
+}

registry/tools/slack.json

@@ -0,0 +1,31 @@
+{
+  "name": "slack",
+  "display_name": "Slack",
+  "kind": "tool",
+  "version": "0.1.0",
+  "description": "Post messages, read channels, and manage conversations via Slack API",
+  "keywords": ["messaging", "chat", "workspace"],
+
+  "source": {
+    "dir": "tools-src/slack",
+    "capabilities": "slack-tool.capabilities.json",
+    "crate_name": "slack-tool"
+  },
+
+  "artifacts": {
+    "wasm32-wasip2": {
+      "url": null,
+      "sha256": null
+    }
+  },
+
+  "auth_summary": {
+    "method": "oauth",
+    "provider": "Slack",
+    "secrets": ["slack_bot_token"],
+    "shared_auth": null,
+    "setup_url": "https://api.slack.com/apps"
+  },
+
+  "tags": ["default", "messaging"]
+}

registry/tools/telegram.json

@@ -0,0 +1,31 @@
+{
+  "name": "telegram",
+  "display_name": "Telegram",
+  "kind": "tool",
+  "version": "0.1.0",
+  "description": "Telegram user-mode integration via MTProto for messages and contacts",
+  "keywords": ["messaging", "chat", "telegram", "mtproto"],
+
+  "source": {
+    "dir": "tools-src/telegram",
+    "capabilities": "telegram-tool.capabilities.json",
+    "crate_name": "telegram-tool"
+  },
+
+  "artifacts": {
+    "wasm32-wasip2": {
+      "url": null,
+      "sha256": null
+    }
+  },
+
+  "auth_summary": {
+    "method": "manual",
+    "provider": "Telegram",
+    "secrets": ["telegram_api_id", "telegram_api_hash"],
+    "shared_auth": null,
+    "setup_url": "https://my.telegram.org/apps"
+  },
+
+  "tags": ["messaging"]
+}

scripts/dev-setup.sh

@@ -0,0 +1,56 @@
+#!/usr/bin/env bash
+# Developer setup script for IronClaw.
+#
+# Gets a fresh checkout ready for development without requiring
+# Docker, PostgreSQL, or any external services.
+#
+# Usage:
+#   ./scripts/dev-setup.sh
+#
+# After running, you can:
+#   cargo check           # default features (postgres + libsql)
+#   cargo test            # default test suite (uses libsql temp DB)
+#   cargo test --all-features         # full test suite
+
+set -euo pipefail
+
+cd "$(dirname "$0")/.."
+
+echo "=== IronClaw Developer Setup ==="
+echo ""
+
+# 1. Check rustup
+if ! command -v rustup &>/dev/null; then
+    echo "ERROR: rustup not found. Install from https://rustup.rs"
+    exit 1
+fi
+echo "[1/5] rustup found: $(rustup --version 2>/dev/null | head -1)"
+
+# 2. Add WASM target (required by build.rs for channel compilation)
+echo "[2/5] Adding wasm32-wasip2 target..."
+rustup target add wasm32-wasip2
+
+# 3. Install wasm-tools (required by build.rs for WASM component model)
+echo "[3/5] Installing wasm-tools..."
+if command -v wasm-tools &>/dev/null; then
+    echo "  wasm-tools already installed: $(wasm-tools --version)"
+else
+    cargo install wasm-tools --locked
+fi
+
+# 4. Verify the project compiles
+echo "[4/5] Running cargo check..."
+cargo check
+
+# 5. Run tests using libsql temp DB (no Docker/external DB needed)
+echo "[5/5] Running tests (no external DB required)..."
+cargo test
+
+echo ""
+echo "=== Setup complete ==="
+echo ""
+echo "Quick start:"
+echo "  cargo run                            # Run with default features"
+echo "  cargo test                           # Test suite (libsql temp DB)"
+echo "  cargo test --all-features            # Full test suite"
+echo "  cargo clippy --all-features          # Lint all code"

src/NETWORK_SECURITY.md

@@ -0,0 +1,566 @@
+# IronClaw Network Security Reference
+
+This document catalogs every network-facing surface in IronClaw, its authentication mechanism, bind address, security controls, and known findings. Use this as the authoritative reference during code reviews that touch network-facing code.
+
+**Last updated:** 2026-02-18
+
+---
+
+## Threat Model
+
+IronClaw operates across four trust boundaries:
+
+| Boundary | Trust Level | Examples |
+|----------|------------|---------|
+| **Local user** | Fully trusted | TUI, web gateway (loopback), CLI commands |
+| **Browser client** | Authenticated | Web UI connected via bearer token; subject to CORS, Origin validation, CSRF protections |
+| **Docker containers** | Untrusted (sandboxed) | Worker containers executing user jobs; isolated via per-job tokens, allowlisted egress, dropped capabilities |
+| **External services** | Untrusted | Webhook senders (Telegram, Slack); authenticated via shared secret |
+
+**Key assumptions:**
+
+- The local machine is single-user. The web gateway and OAuth listener bind to loopback and do not defend against other local users.
+- Docker containers are adversarial. A compromised container should not be able to access other jobs, exfiltrate secrets, or reach the host network beyond the orchestrator API.
+- Webhook senders must prove knowledge of the shared secret. The secret is never transmitted in the clear by IronClaw itself.
+- MCP server URLs are operator-configured and treated as trusted destinations (see [MCP Client](#mcp-client)).
+
+---
+
+## Network Surface Inventory
+
+| Listener | Default Port | Default Bind | Auth Mechanism | Config Env Var | Source |
+|----------|-------------|-------------|----------------|----------------|--------|
+| Web Gateway | 3000 | `127.0.0.1` | Bearer token (constant-time) | `GATEWAY_HOST`, `GATEWAY_PORT`, `GATEWAY_AUTH_TOKEN` | `server.rs` — `start_server()` |
+| HTTP Webhook Server | 8080 | `0.0.0.0` | Shared secret (body field) | `HTTP_HOST`, `HTTP_PORT`, `HTTP_WEBHOOK_SECRET` | `webhook_server.rs` — `start()` |
+| Orchestrator Internal API | 50051 | `127.0.0.1` (macOS/Win) / `0.0.0.0` (Linux) | Per-job bearer token (constant-time) | `ORCHESTRATOR_PORT` | `api.rs` — `OrchestratorApi::start()` |
+| OAuth Callback Listener | 9876 | `127.0.0.1` | None (ephemeral, 5-min timeout) | N/A (hardcoded) | `oauth_defaults.rs` — `bind_callback_listener()` |
+| Sandbox HTTP Proxy | OS-assigned (ephemeral) | `127.0.0.1` | None (loopback only) | N/A (auto-assigned) | `proxy/http.rs` — `SandboxProxy::start()` |
+
+---
+
+## 1. Web Gateway
+
+**Source:** `src/channels/web/server.rs`, `src/channels/web/auth.rs`
+
+### Bind Address
+
+Configurable via `GATEWAY_HOST` (default `127.0.0.1`) and `GATEWAY_PORT` (default `3000`). The gateway is designed as a local-first, single-user service.
+
+**Reference:** `src/config.rs` — `gateway_host` default (`"127.0.0.1"`), `gateway_port` default (`3000`)
+
+### Authentication
+
+Bearer token middleware applied to all `/api/*` routes via `route_layer`. Token checked in two locations:
+
+1. `Authorization: Bearer <token>` header (primary)
+2. `?token=<token>` query parameter (fallback for SSE `EventSource` which cannot set headers)
+
+Both paths use **constant-time comparison** via `subtle::ConstantTimeEq` (`ct_eq`).
+
+**Reference:** `src/channels/web/auth.rs` — `auth_middleware()`, header check and query-param fallback both use `ct_eq`
+
+If `GATEWAY_AUTH_TOKEN` is not set, a random hex token is generated at startup.
+
+### Unauthenticated Routes
+
+| Route | Purpose | Response |
+|-------|---------|----------|
+| `/api/health` | Health check endpoint | `{"status":"healthy","channel":"gateway"}` — no version, uptime, or fingerprinting data |
+| `/` | Static HTML (embedded) | Single-page app shell |
+| `/style.css` | Static CSS (embedded) | Stylesheet |
+| `/app.js` | Static JS (embedded) | Client-side app |
+
+### CORS Policy
+
+Restricted to a two-origin allowlist (not browser same-origin policy, but a CORS allowlist that achieves equivalent protection):
+
+- `http://<bind_ip>:<bind_port>`
+- `http://localhost:<bind_port>`
+
+Allowed methods: `GET`, `POST`, `PUT`, `DELETE`. Allowed headers: `Content-Type`, `Authorization`. Credentials allowed.
+
+**Reference:** `src/channels/web/server.rs` — `CorsLayer::new()` block
+
+### WebSocket Origin Validation
+
+The `/api/chat/ws` endpoint has two layers of protection:
+
+1. **Bearer token auth** — the route is inside the `protected` router with `route_layer`, so `auth_middleware` runs before the handler. The token is passed via the `Authorization: Bearer` header on the HTTP upgrade request (not via query parameter).
+
+2. **Origin header validation** (inside the handler) as a defense-in-depth guard against cross-site WebSocket hijacking (CSWSH):
+   - Origin header is **required** — missing Origin returns 403 (browsers always send it for WS upgrades; absence implies a non-browser client)
+   - Origin host is extracted by stripping scheme and port, then compared **exactly** against `localhost`, `127.0.0.1`, and `[::1]`
+   - Partial matches like `localhost.evil.com` are rejected because the check extracts the host portion before the first `:` or `/`
+
+**Reference:** `src/channels/web/server.rs` — `chat_ws_handler()` (origin validation block)
+
+### Rate Limiting
+
+Chat endpoint (`/api/chat/send`) enforces a sliding-window rate limit: **30 requests per 60 seconds** (global, not per-IP — single-user gateway).
+
+**Reference:** `src/channels/web/server.rs` — `RateLimiter` struct, `chat_rate_limiter` field
+
+### Body Limits
+
+- Global: **1 MB** max request body (`DefaultBodyLimit::max(1024 * 1024)`)
+- **Reference:** `src/channels/web/server.rs` — `.layer(DefaultBodyLimit::max(...))`
+
+### Project File Serving
+
+The `/projects/{project_id}/*` routes serve files from project directories. These are **behind auth middleware** to prevent unauthorized file access.
+
+**Reference:** `src/channels/web/server.rs` — project file routes in `protected` router
+
+### Security Headers
+
+The gateway sets the following security headers on all responses (via `SetResponseHeaderLayer::if_not_present`, so handlers can override):
+
+- `X-Content-Type-Options: nosniff` — prevents MIME-sniffing
+- `X-Frame-Options: DENY` — prevents clickjacking via iframes
+
+**Reference:** `src/channels/web/server.rs` — `SetResponseHeaderLayer` calls
+
+### Graceful Shutdown
+
+Shutdown is triggered via a `oneshot::Sender` stored in `GatewayState::shutdown_tx`. The server uses `axum::serve(...).with_graceful_shutdown(...)` to drain in-flight requests before closing the listener.
+
+**Reference:** `src/channels/web/server.rs` — `shutdown_tx` / `shutdown_rx` setup
+
+---
+
+## 2. HTTP Webhook Server
+
+**Source:** `src/channels/webhook_server.rs`, `src/channels/http.rs`
+
+### Bind Address
+
+Configurable via `HTTP_HOST` (default `0.0.0.0`) and `HTTP_PORT` (default `8080`).
+
+**WARNING:** The default bind address is `0.0.0.0`, meaning the webhook server listens on **all interfaces** by default. This is intentional (webhooks must be reachable from external services like Telegram/Slack), but operators should be aware of the exposure.
+
+**Reference:** `src/config.rs` — `http_host` default (`"0.0.0.0"`), `http_port` default (`8080`)
+
+### Authentication
+
+Webhook secret is passed **in the JSON request body** (`secret` field), not as a header. The secret is compared using **constant-time** `subtle::ConstantTimeEq` (`ct_eq`).
+
+The secret is required to start the channel — if `HTTP_WEBHOOK_SECRET` is not set, `start()` returns an error.
+
+**CSRF note:** Because the secret is in the JSON body (not a cookie or header that browsers auto-attach), a cross-origin form POST cannot forge a valid request. Browsers would send `application/x-www-form-urlencoded`, which the `Json<T>` extractor rejects with HTTP 415. Even if `Content-Type` were spoofed via CORS preflight, the attacker would need the secret value, which is never stored in the browser.
+
+**Reference:** `src/channels/http.rs` — `webhook_handler()` (secret validation with `ct_eq`), `start()` (required-secret check)
+
+### Content-Type Validation
+
+The webhook endpoint uses axum's `Json<WebhookRequest>` extractor, which enforces `Content-Type: application/json`. Requests with missing or incorrect Content-Type are rejected with **HTTP 415 Unsupported Media Type** before the handler body executes. Malformed JSON bodies are rejected with **HTTP 422 Unprocessable Entity**.
+
+**Reference:** `src/channels/http.rs` — `webhook_handler()` function signature (`Json(req): Json<WebhookRequest>`)
+
+### Rate Limiting
+
+**60 requests per minute**, enforced via a mutex-protected sliding window.
+
+**Reference:** `src/channels/http.rs` — `MAX_REQUESTS_PER_MINUTE` constant, rate-limit check in `webhook_handler()`
+
+### Body Limits
+
+- JSON body: **64 KB** max (`MAX_BODY_BYTES`)
+- Message content: **32 KB** max (`MAX_CONTENT_BYTES`)
+- Pending synchronous responses: **100 max** (`MAX_PENDING_RESPONSES`)
+- Synchronous response timeout: **60 seconds**
+
+**Reference:** `src/channels/http.rs` — constants block (`MAX_BODY_BYTES`, `MAX_CONTENT_BYTES`, `MAX_PENDING_RESPONSES`, `MAX_REQUESTS_PER_MINUTE`)
+
+### Routes
+
+| Route | Auth | Purpose | Response |
+|-------|------|---------|----------|
+| `/health` | None | Health check | `{"status":"healthy","channel":"http"}` — no fingerprinting data |
+| `/webhook` | Webhook secret | Receive messages | Webhook response |
+
+### Graceful Shutdown
+
+Shutdown is triggered via a `oneshot::Sender` stored on the `WebhookServer` struct. The server uses `axum::serve(...).with_graceful_shutdown(...)`. The public `shutdown()` method sends the signal and awaits the task join handle, ensuring a clean drain-and-wait.
+
+**Reference:** `src/channels/webhook_server.rs` — `shutdown()` method
+
+---
+
+## 3. Orchestrator Internal API
+
+**Source:** `src/orchestrator/api.rs`, `src/orchestrator/auth.rs`
+
+### Bind Address
+
+Platform-dependent:
+
+- **macOS / Windows**: `127.0.0.1:<port>` — Docker Desktop routes `host.docker.internal` through its VM to `127.0.0.1`
+- **Linux**: `0.0.0.0:<port>` — containers reach the host via the Docker bridge gateway (`172.17.0.1`), which is not loopback
+
+Default port: `50051`.
+
+**Reference:** `src/orchestrator/api.rs` — `OrchestratorApi::start()`, platform-conditional bind address block
+
+### Authentication
+
+Per-job bearer tokens validated by `worker_auth_middleware`:
+
+1. Tokens are **cryptographically random** (32 bytes, hex-encoded = 64 chars)
+2. Tokens are **scoped to a specific job_id** — a token for job A cannot access endpoints for job B
+3. Comparison uses **constant-time** `subtle::ConstantTimeEq`
+4. Tokens are **ephemeral** (in-memory only, never persisted to disk or DB)
+5. Tokens and associated credential grants are **revoked** when the container is cleaned up
+
+**Reference:** `src/orchestrator/auth.rs` — `TokenStore::create_token()`, `TokenStore::validate()`, `generate_token()`
+
+### Token Extraction
+
+The middleware extracts the job UUID from the URL path (`/worker/{job_id}/...`) and validates the `Authorization: Bearer` header against the stored token for that specific job.
+
+**Reference:** `src/orchestrator/auth.rs` — `worker_auth_middleware()`, `extract_job_id_from_path()`
+
+### Credential Grants
+
+The orchestrator can grant per-job access to specific secrets from the encrypted secrets store. Grants are:
+
+- Stored alongside the token in the `TokenStore`
+- Scoped to specific `(secret_name, env_var)` pairs
+- Revoked when the job token is revoked
+- Decrypted on-demand when the worker requests `/worker/{job_id}/credentials`
+
+**Reference:** `src/orchestrator/auth.rs` — `CredentialGrant` struct, `src/orchestrator/api.rs` — `get_credentials_handler()`
+
+### Rate Limiting
+
+**None.** The orchestrator API has no rate limiting. All `/worker/*` endpoints are authenticated via per-job bearer tokens, but a compromised container could spam authenticated endpoints without throttling.
+
+**Mitigation:** Tokens are scoped per-job so a compromised container can only abuse its own job's endpoints. Container execution is time-bounded (see [Docker Container Security](#docker-container-security)), which limits the window for abuse.
+
+### Routes
+
+| Route | Auth | Purpose | Response |
+|-------|------|---------|----------|
+| `/health` | None | Health check | `"ok"` (plain text) — no fingerprinting data |
+| `/worker/{job_id}/job` | Per-job token | Get job description | Job JSON |
+| `/worker/{job_id}/llm/complete` | Per-job token | Proxy LLM completion | LLM response |
+| `/worker/{job_id}/llm/complete_with_tools` | Per-job token | Proxy LLM tool completion | LLM response |
+| `/worker/{job_id}/status` | Per-job token | Report worker status | Ack |
+| `/worker/{job_id}/complete` | Per-job token | Report job completion | Ack |
+| `/worker/{job_id}/event` | Per-job token | Send job events (SSE broadcast) | Ack |
+| `/worker/{job_id}/prompt` | Per-job token | Poll for follow-up prompts | Prompt or empty |
+| `/worker/{job_id}/credentials` | Per-job token | Retrieve decrypted credentials | Credentials JSON |
+
+### Graceful Shutdown
+
+**None.** The orchestrator calls `axum::serve(listener, router).await?` without `.with_graceful_shutdown()`. The server stops only when the task is dropped (process exit or tokio task cancellation). In-flight requests may be interrupted.
+
+**Reference:** `src/orchestrator/api.rs` — `OrchestratorApi::start()`
+
+---
+
+## 4. OAuth Callback Listener
+
+**Source:** `src/cli/oauth_defaults.rs`
+
+### Bind Address
+
+Always binds to **loopback only**: `127.0.0.1:9876`. Falls back to `[::1]:9876` (IPv6 loopback) if IPv4 binding fails for reasons other than `AddrInUse`. If the port is already in use, the error is returned immediately (fail-fast).
+
+Both IPv4 and IPv6 loopback addresses are security-equivalent — they are only reachable from the local machine.
+
+**Reference:** `src/cli/oauth_defaults.rs` — `OAUTH_CALLBACK_PORT` constant, `bind_callback_listener()`
+
+### Lifecycle
+
+The listener is **ephemeral** — it is started only when an OAuth flow is initiated (e.g., `ironclaw tool auth <name>`) and shut down after the callback is received or the timeout expires.
+
+### Timeout
+
+**5-minute timeout** (`Duration::from_secs(300)`). If the user does not complete the OAuth flow in the browser within 5 minutes, the listener shuts down.
+
+**Reference:** `src/cli/oauth_defaults.rs` — `tokio::time::timeout(Duration::from_secs(300), ...)`
+
+### Security Controls
+
+- **HTML escaping**: Provider names displayed in the landing page are HTML-escaped to prevent XSS (escapes `&`, `<`, `>`, `"`, `'`)
+- **Error parameter checking**: The handler checks for `error=` in the callback query string before extracting the auth code
+- **URL decoding**: Callback parameters are URL-decoded safely
+
+**Reference:** `src/cli/oauth_defaults.rs` — `html_escape()`
+
+### Built-in OAuth Credentials
+
+Google OAuth client ID and secret are compiled into the binary (with compile-time override via `IRONCLAW_GOOGLE_CLIENT_ID` / `IRONCLAW_GOOGLE_CLIENT_SECRET`). As noted in the source, Google Desktop App client secrets are [not actually secret](https://developers.google.com/identity/protocols/oauth2/native-app) per Google's documentation.
+
+**Reference:** `src/cli/oauth_defaults.rs` — `GOOGLE_CLIENT_ID` / `GOOGLE_CLIENT_SECRET` constants
+
+### Graceful Shutdown
+
+Implicit. The listener is a raw `TcpListener` (not axum) inside a `tokio::time::timeout` future. Once the authorization code or error is received, the future returns and the `TcpListener` is dropped, closing the port. No explicit shutdown signal is needed.
+
+**Reference:** `src/cli/oauth_defaults.rs` — `wait_for_callback()`
+
+---
+
+## 5. Sandbox HTTP Proxy
+
+**Source:** `src/sandbox/proxy/http.rs`, `src/sandbox/proxy/allowlist.rs`, `src/sandbox/proxy/policy.rs`
+
+### Bind Address
+
+Always binds to **`127.0.0.1`** (localhost only). Port is OS-assigned (port `0`, ephemeral). Falls back to `[::1]` (IPv6 loopback) if IPv4 is unavailable.
+
+Both IPv4 and IPv6 loopback addresses are security-equivalent — they are only reachable from the local machine.
+
+**Reference:** `src/sandbox/proxy/http.rs` — `SandboxProxy::start()`, `TcpListener::bind("127.0.0.1:0")`
+
+### Purpose
+
+Acts as an HTTP/HTTPS proxy for Docker sandbox containers. Containers are configured with `http_proxy` / `https_proxy` environment variables pointing to this proxy, so all outbound HTTP traffic is routed through it.
+
+### Domain Allowlisting
+
+All requests are validated against a domain allowlist before being forwarded:
+
+- **Empty allowlist = deny all** (fail-closed default)
+- Supports exact matches and wildcard patterns (`*.example.com`)
+- Validates URL scheme (HTTP/HTTPS only, rejects `ftp://`, `file://`, etc.)
+
+**Reference:** `src/sandbox/proxy/allowlist.rs` — `DomainAllowlist` struct, `is_allowed()` method
+
+### HTTPS Tunneling (CONNECT)
+
+- CONNECT requests for HTTPS tunneling are subject to the same allowlist
+- **30-minute timeout** on established tunnels to prevent indefinite holds
+- **No MITM**: the proxy cannot inspect or inject credentials into HTTPS traffic (by design — containers that need credentials must use the orchestrator's `/worker/{job_id}/credentials` endpoint)
+
+**Reference:** `src/sandbox/proxy/http.rs` — `handle_connect()` function
+
+### Credential Injection (HTTP only)
+
+For plain HTTP requests to allowed hosts, the proxy can inject credentials:
+
+- Bearer tokens in `Authorization` header
+- Custom headers (e.g., `X-API-Key`)
+- Query parameters
+- Credentials are resolved at request time from the encrypted secrets store
+- Credentials never enter the container's environment or filesystem
+
+**Reference:** `src/sandbox/proxy/http.rs` — credential injection block in `handle_request()`
+
+### Hop-by-Hop Header Filtering
+
+The proxy strips hop-by-hop headers to prevent header-based attacks: `connection`, `keep-alive`, `proxy-authenticate`, `proxy-authorization`, `te`, `trailers`, `transfer-encoding`, `upgrade`.
+
+**Reference:** `src/sandbox/proxy/http.rs` — `is_hop_by_hop_header()`
+
+### Docker Container Security
+
+Containers that use the proxy are configured with defense-in-depth:
+
+| Control | Setting | Reference |
+|---------|---------|-----------|
+| Capabilities | Drop ALL, add only CHOWN | `src/sandbox/container.rs` — `cap_drop` / `cap_add` |
+| Privilege escalation | `no-new-privileges:true` | `src/sandbox/container.rs` — `security_opt` |
+| Root filesystem | Read-only (except FullAccess policy) | `src/sandbox/container.rs` — `readonly_rootfs` |
+| User | Non-root (UID 1000:1000) | `src/sandbox/container.rs` — `user` field |
+| Network | Bridge mode (isolated) | `src/sandbox/container.rs` — `network_mode` |
+| Tmpfs | `/tmp` (512 MB), `/home/sandbox/.cargo/registry` (1 GB) | `src/sandbox/container.rs` — `tmpfs` block |
+| Auto-remove | Enabled | `src/sandbox/container.rs` — `auto_remove` |
+| Output limits | Configurable max stdout/stderr | `src/sandbox/container.rs` — `collect_logs()` |
+| Timeout | Enforced with forced container removal | `src/sandbox/container.rs` — `tokio::time::timeout` in `run()` |
+
+### Graceful Shutdown
+
+Shutdown is triggered via a `oneshot::Sender` stored on the proxy. The accept loop uses `tokio::select!` to race `listener.accept()` against the shutdown signal. The `stop()` method fires the signal; the loop breaks on the next iteration. Note: `stop()` does not await a join handle, so there is no drain-and-wait for in-flight connections.
+
+**Reference:** `src/sandbox/proxy/http.rs` — `stop()` method, `tokio::select!` loop
+
+---
+
+## Egress Controls
+
+### WASM Tool HTTP Requests
+
+WASM tools execute HTTP requests through the host runtime, subject to:
+
+1. **Endpoint allowlist** — declared in `<tool>.capabilities.json`, validated by `AllowlistValidator`
+   - Host matching (exact or wildcard)
+   - Path prefix matching
+   - HTTP method restriction
+   - HTTPS required by default
+   - Userinfo in URLs (`user:pass@host`) rejected to prevent allowlist bypass
+   - Path traversal (`../`, `%2e%2e/`) normalized and blocked
+   - Invalid percent-encoding rejected
+   - **Reference:** `src/tools/wasm/allowlist.rs`
+
+2. **Credential injection** — secrets injected at the host boundary by `CredentialInjector`
+   - WASM code never sees actual credential values
+   - Secrets must be in the tool's `allowed_secrets` list
+   - Injection supports: Bearer header, Basic auth, custom header, query parameter
+   - **Reference:** `src/tools/wasm/credential_injector.rs`
+
+3. **Leak detection** — `LeakDetector` scans both outbound requests and inbound responses for secret patterns
+   - Runs at two points: before sending and after receiving
+   - Uses Aho-Corasick for fast multi-pattern matching
+   - **Reference:** `src/safety/leak_detector.rs`
+
+### Built-in HTTP Tool
+
+The `http` tool (`src/tools/builtin/http.rs`) has its own SSRF protections:
+
+| Protection | Details | Reference |
+|-----------|---------|-----------|
+| HTTPS only | Rejects `http://` URLs | `http.rs` — scheme check |
+| Localhost blocked | Rejects `localhost` and `*.localhost` | `http.rs` — host check |
+| Private IP blocked | Rejects RFC 1918, loopback, link-local, multicast, unspecified | `http.rs` — `is_disallowed_ip()` |
+| DNS rebinding | Resolves hostname and checks all resolved IPs against blocklist | `http.rs` — DNS resolution block |
+| Cloud metadata | Blocks `169.254.169.254` (AWS/GCP metadata endpoint) | `http.rs` — `is_disallowed_ip()` |
+| Redirect blocking | Returns error on 3xx responses (prevents SSRF via redirect) | `http.rs` — status code check |
+| Response size limit | **5 MB** max, enforced both via Content-Length header and streaming | `http.rs` — `MAX_RESPONSE_SIZE` constant, streaming cap |
+| Outbound leak scan | Scans URL, headers, and body for secrets before sending | `http.rs` — `LeakDetector::scan_http_request()` |
+| Approval required | Requires user approval before execution | `http.rs` — `requires_approval()` returns `true` |
+| Timeout | 30 seconds default | `http.rs` — `reqwest::Client` builder |
+| No redirects | `redirect::Policy::none()` — redirects are not followed | `http.rs` — `reqwest::Client` builder |
+
+### MCP Client
+
+MCP servers are external processes accessed via HTTP. The MCP client (`src/tools/mcp/client.rs`) uses `reqwest` with a 30-second timeout but has **no SSRF protections** — it connects to whatever URL is configured for the MCP server.
+
+This is by design: MCP server URLs come from **operator-controlled configuration** (config files, environment variables, or the CLI `tool install` command), not from user input or LLM output. A compromised config file is outside IronClaw's threat model — it would imply the operator's machine is already compromised.
+
+**Reference:** `src/tools/mcp/client.rs` — `reqwest::Client` builder
+
+### Sandbox Domain Allowlists
+
+Sandbox containers route all HTTP traffic through the proxy, which enforces a domain allowlist. The allowlist is built from:
+
+1. A default set of domains (`src/sandbox/config.rs` — `default_allowlist()`)
+2. Additional domains from `SANDBOX_EXTRA_DOMAINS` env var (comma-separated)
+
+**Reference:** `src/config.rs` — sandbox allowlist assembly
+
+---
+
+## Authentication Mechanisms Summary
+
+| Mechanism | Constant-Time | Used By | Reference |
+|-----------|:------------:|---------|-----------|
+| Gateway bearer token | Yes | Web gateway (header + query) | `src/channels/web/auth.rs` — `auth_middleware()` |
+| Webhook shared secret | Yes | HTTP webhook (`ct_eq` comparison) | `src/channels/http.rs` — `webhook_handler()` |
+| Per-job bearer token | Yes | Orchestrator worker API | `src/orchestrator/auth.rs` — `TokenStore::validate()` |
+| OAuth callback | N/A | CLI OAuth flow (no auth, loopback-only) | `src/cli/oauth_defaults.rs` — `bind_callback_listener()` |
+| Sandbox proxy | N/A | No auth (loopback-only, ephemeral) | `src/sandbox/proxy/http.rs` — `SandboxProxy::start()` |
+
+---
+
+## Known Security Findings
+
+### Open
+
+#### F-2. No TLS at the application layer
+
+**Severity:** Low (for local deployment)
+**Details:** None of the listeners terminate TLS. All communication is plain HTTP.
+**Mitigation:** The web gateway and OAuth callback bind to loopback by default. For production, users are expected to front the gateway with a reverse proxy (nginx, Caddy) or tunnel (Cloudflare, ngrok) that provides TLS.
+**Recommendation:** Document the requirement for a TLS-terminating reverse proxy in deployment guides.
+
+#### F-3. Orchestrator binds to `0.0.0.0` on Linux
+
+**Severity:** Medium
+**Location:** `src/orchestrator/api.rs` — platform-conditional bind in `OrchestratorApi::start()`
+**Details:** On Linux, the orchestrator API binds to all interfaces because Docker containers reach the host via the bridge gateway (`172.17.0.1`), not loopback. This means the API is reachable from any network interface on the host.
+**Mitigation:** All `/worker/*` endpoints require per-job bearer tokens (constant-time, cryptographically random). The `/health` endpoint is the only unauthenticated route and returns only `"ok"`. Firewall rules should block external access to port 50051.
+**Recommendation:** Document firewall requirements for Linux deployments. Consider binding to the Docker bridge IP (`172.17.0.1`) instead of `0.0.0.0`.
+
+#### F-6. WebSocket/SSE connection limit
+
+**Severity:** Info
+**Details:** The `SseManager` enforces a hard limit of **100 concurrent connections** (`MAX_CONNECTIONS` constant in `src/channels/web/sse.rs`). Both SSE subscribers and WebSocket connections share this counter. When exceeded, new WebSocket upgrades are rejected with a warning log and the connection is immediately closed.
+**Reference:** `src/channels/web/sse.rs` — `MAX_CONNECTIONS`, `src/channels/web/ws.rs` — `handle_ws_connection()` early return
+
+#### F-7. Orchestrator API has no rate limiting
+
+**Severity:** Low
+**Details:** The orchestrator API has no request-rate throttling. A compromised container could spam authenticated endpoints (e.g., `/worker/{job_id}/llm/complete`) to drive up LLM costs or degrade service for other jobs.
+**Mitigation:** Tokens are scoped per-job, limiting blast radius. Container execution is time-bounded by the sandbox timeout, which caps the abuse window.
+**Recommendation:** Consider adding per-token rate limiting on the LLM proxy endpoints.
+
+#### F-8. Orchestrator API has no graceful shutdown
+
+**Severity:** Info
+**Details:** The orchestrator calls `axum::serve(listener, router).await?` without `.with_graceful_shutdown()`. In-flight requests (including LLM proxy calls) may be interrupted during process shutdown.
+**Reference:** `src/orchestrator/api.rs` — `OrchestratorApi::start()`
+
+### Resolved / Mitigated
+
+<details>
+<summary>Resolved and mitigated findings (click to expand)</summary>
+
+#### F-1. ~~Webhook secret comparison is not constant-time~~ (Resolved)
+
+**Severity:** Low
+**Location:** `src/channels/http.rs` — `webhook_handler()`
+**Status:** Resolved — webhook secret now uses `subtle::ConstantTimeEq` (`ct_eq`), consistent with web gateway and orchestrator auth.
+
+#### F-4. ~~HTTP webhook server binds to `0.0.0.0` by default~~ (Mitigated)
+
+**Severity:** Low
+**Location:** `src/config.rs`, `src/main.rs`
+**Status:** Mitigated — a `tracing::warn!` is now emitted at startup when the webhook server binds to an unspecified address (`0.0.0.0` or `::`), advising operators to set `HTTP_HOST=127.0.0.1` to restrict to localhost. The default bind address remains `0.0.0.0`, so webhook exposure is still controlled by operator configuration and external network controls (firewalls, ingress rules).
+
+#### F-5. ~~Missing security headers on web gateway~~ (Mitigated)
+
+**Severity:** Low
+**Status:** Mitigated — `X-Content-Type-Options: nosniff` and `X-Frame-Options: DENY` are now set on all gateway responses via `SetResponseHeaderLayer::if_not_present`. Layer ordering ensures these headers are applied even to error responses generated by inner layers (e.g., `DefaultBodyLimit` 413 rejections).
+
+</details>
+
+---
+
+## Review Checklist for Network Changes
+
+Use this checklist for any PR that adds or modifies network-facing code.
+
+### New Listener
+
+- [ ] **Bind address**: Does it bind to loopback (`127.0.0.1`) or all interfaces (`0.0.0.0`)? Justify if `0.0.0.0`.
+- [ ] **Port configuration**: Is the port configurable via env var? Is a sensible default set?
+- [ ] **Authentication**: Is auth required? If yes, is it constant-time? If no, why not?
+- [ ] **Rate limiting**: Is there a rate limiter? What are the limits?
+- [ ] **Body size limit**: Is `DefaultBodyLimit` (or equivalent) set?
+- [ ] **Content-Type validation**: Does the handler validate Content-Type (e.g., via axum `Json<T>` extractor)?
+- [ ] **Graceful shutdown**: Does the listener support graceful shutdown via oneshot or similar?
+- [ ] **Inventory update**: Is this document updated with the new listener?
+
+### New Route on Existing Listener
+
+- [ ] **Auth layer**: Is the route behind the auth middleware? If public, why?
+- [ ] **Input validation**: Are path parameters, query parameters, and body fields validated?
+- [ ] **Error responses**: Do error responses avoid leaking internal details?
+
+### Egress (Outbound HTTP)
+
+- [ ] **SSRF protection**: Does the code block private IPs, localhost, and cloud metadata endpoints?
+- [ ] **DNS rebinding**: Are resolved IPs checked (not just the hostname)?
+- [ ] **Redirect handling**: Are redirects blocked or validated?
+- [ ] **Response size**: Is there a max response size?
+- [ ] **Timeout**: Is a request timeout set?
+- [ ] **Leak detection**: Is the outbound request scanned for secrets?
+
+### Credential Handling
+
+- [ ] **Constant-time comparison**: Are secrets compared with `subtle::ConstantTimeEq`?
+- [ ] **No logging**: Are credentials excluded from log messages?
+- [ ] **Ephemeral storage**: Are tokens stored in memory only (not persisted)?
+- [ ] **Scope**: Are credentials scoped to the minimum necessary (per-job, per-tool)?
+- [ ] **Revocation**: Are credentials revoked when no longer needed?
+
+### Container / Sandbox
+
+- [ ] **Capabilities**: Are all capabilities dropped except what's needed?
+- [ ] **Filesystem**: Is the root filesystem read-only?
+- [ ] **User**: Does the container run as non-root?
+- [ ] **Network**: Is network access routed through the proxy?
+- [ ] **Timeout**: Is there an execution timeout with forced cleanup?
+- [ ] **Output limits**: Are stdout/stderr capped?

src/agent/commands.rs

@@ -0,0 +1,507 @@
+//! System commands and job handlers for the agent.
+//!
+//! Extracted from `agent_loop.rs` to isolate the /help, /model, /status,
+//! and other command processing from the core agent loop.
+
+use std::sync::Arc;
+
+use tokio::sync::Mutex;
+use uuid::Uuid;
+
+use crate::agent::session::Session;
+use crate::agent::submission::SubmissionResult;
+use crate::agent::{Agent, MessageIntent};
+use crate::channels::{IncomingMessage, StatusUpdate};
+use crate::error::Error;
+use crate::llm::{ChatMessage, Reasoning};
+
+impl Agent {
+    /// Handle job-related intents without turn tracking.
+    pub(super) async fn handle_job_or_command(
+        &self,
+        intent: MessageIntent,
+        message: &IncomingMessage,
+    ) -> Result<SubmissionResult, Error> {
+        // Send thinking status for non-trivial operations
+        if let MessageIntent::CreateJob { .. } = &intent {
+            let _ = self
+                .channels
+                .send_status(
+                    &message.channel,
+                    StatusUpdate::Thinking("Processing...".into()),
+                    &message.metadata,
+                )
+                .await;
+        }
+
+        let response = match intent {
+            MessageIntent::CreateJob {
+                title,
+                description,
+                category,
+            } => {
+                self.handle_create_job(&message.user_id, title, description, category)
+                    .await?
+            }
+            MessageIntent::CheckJobStatus { job_id } => {
+                self.handle_check_status(&message.user_id, job_id).await?
+            }
+            MessageIntent::CancelJob { job_id } => {
+                self.handle_cancel_job(&message.user_id, &job_id).await?
+            }
+            MessageIntent::ListJobs { filter } => {
+                self.handle_list_jobs(&message.user_id, filter).await?
+            }
+            MessageIntent::HelpJob { job_id } => {
+                self.handle_help_job(&message.user_id, &job_id).await?
+            }
+            MessageIntent::Command { command, args } => {
+                match self.handle_command(&command, &args).await? {
+                    Some(s) => s,
+                    None => return Ok(SubmissionResult::Ok { message: None }), // Shutdown signal
+                }
+            }
+            _ => "Unknown intent".to_string(),
+        };
+        Ok(SubmissionResult::response(response))
+    }
+
+    async fn handle_create_job(
+        &self,
+        user_id: &str,
+        title: String,
+        description: String,
+        category: Option<String>,
+    ) -> Result<String, Error> {
+        // Create job context
+        let job_id = self
+            .context_manager
+            .create_job_for_user(user_id, &title, &description)
+            .await?;
+
+        // Update category if provided
+        if let Some(cat) = category {
+            self.context_manager
+                .update_context(job_id, |ctx| {
+                    ctx.category = Some(cat);
+                })
+                .await?;
+        }
+
+        // Persist new job to database (fire-and-forget)
+        if let Some(store) = self.store()
+            && let Ok(ctx) = self.context_manager.get_context(job_id).await
+        {
+            let store = store.clone();
+            tokio::spawn(async move {
+                if let Err(e) = store.save_job(&ctx).await {
+                    tracing::warn!("Failed to persist new job {}: {}", job_id, e);
+                }
+            });
+        }
+
+        // Schedule for execution
+        self.scheduler.schedule(job_id).await?;
+
+        Ok(format!(
+            "Created job: {}\nID: {}\n\nThe job has been scheduled and is now running.",
+            title, job_id
+        ))
+    }
+
+    async fn handle_check_status(
+        &self,
+        user_id: &str,
+        job_id: Option<String>,
+    ) -> Result<String, Error> {
+        match job_id {
+            Some(id) => {
+                let uuid = Uuid::parse_str(&id)
+                    .map_err(|_| crate::error::JobError::NotFound { id: Uuid::nil() })?;
+
+                let ctx = self.context_manager.get_context(uuid).await?;
+                if ctx.user_id != user_id {
+                    return Err(crate::error::JobError::NotFound { id: uuid }.into());
+                }
+
+                Ok(format!(
+                    "Job: {}\nStatus: {:?}\nCreated: {}\nStarted: {}\nActual cost: {}",
+                    ctx.title,
+                    ctx.state,
+                    ctx.created_at.format("%Y-%m-%d %H:%M:%S"),
+                    ctx.started_at
+                        .map(|t| t.format("%Y-%m-%d %H:%M:%S").to_string())
+                        .unwrap_or_else(|| "Not started".to_string()),
+                    ctx.actual_cost
+                ))
+            }
+            None => {
+                // Show summary of all jobs
+                let summary = self.context_manager.summary_for(user_id).await;
+                Ok(format!(
+                    "Jobs summary:\n  Total: {}\n  In Progress: {}\n  Completed: {}\n  Failed: {}\n  Stuck: {}",
+                    summary.total,
+                    summary.in_progress,
+                    summary.completed,
+                    summary.failed,
+                    summary.stuck
+                ))
+            }
+        }
+    }
+
+    async fn handle_cancel_job(&self, user_id: &str, job_id: &str) -> Result<String, Error> {
+        let uuid = Uuid::parse_str(job_id)
+            .map_err(|_| crate::error::JobError::NotFound { id: Uuid::nil() })?;
+
+        let ctx = self.context_manager.get_context(uuid).await?;
+        if ctx.user_id != user_id {
+            return Err(crate::error::JobError::NotFound { id: uuid }.into());
+        }
+
+        self.scheduler.stop(uuid).await?;
+
+        Ok(format!("Job {} has been cancelled.", job_id))
+    }
+
+    async fn handle_list_jobs(
+        &self,
+        user_id: &str,
+        _filter: Option<String>,
+    ) -> Result<String, Error> {
+        let jobs = self.context_manager.all_jobs_for(user_id).await;
+
+        if jobs.is_empty() {
+            return Ok("No jobs found.".to_string());
+        }
+
+        let mut output = String::from("Jobs:\n");
+        for job_id in jobs {
+            if let Ok(ctx) = self.context_manager.get_context(job_id).await
+                && ctx.user_id == user_id
+            {
+                output.push_str(&format!("  {} - {} ({:?})\n", job_id, ctx.title, ctx.state));
+            }
+        }
+
+        Ok(output)
+    }
+
+    async fn handle_help_job(&self, user_id: &str, job_id: &str) -> Result<String, Error> {
+        let uuid = Uuid::parse_str(job_id)
+            .map_err(|_| crate::error::JobError::NotFound { id: Uuid::nil() })?;
+
+        let ctx = self.context_manager.get_context(uuid).await?;
+        if ctx.user_id != user_id {
+            return Err(crate::error::JobError::NotFound { id: uuid }.into());
+        }
+
+        if ctx.state == crate::context::JobState::Stuck {
+            // Attempt recovery
+            self.context_manager
+                .update_context(uuid, |ctx| ctx.attempt_recovery())
+                .await?
+                .map_err(|s| crate::error::JobError::ContextError {
+                    id: uuid,
+                    reason: s,
+                })?;
+
+            // Reschedule
+            self.scheduler.schedule(uuid).await?;
+
+            Ok(format!(
+                "Job {} was stuck. Attempting recovery (attempt #{}).",
+                job_id,
+                ctx.repair_attempts + 1
+            ))
+        } else {
+            Ok(format!(
+                "Job {} is not stuck (current state: {:?}). No help needed.",
+                job_id, ctx.state
+            ))
+        }
+    }
+
+    /// Trigger a manual heartbeat check.
+    pub(super) async fn process_heartbeat(&self) -> Result<SubmissionResult, Error> {
+        let Some(workspace) = self.workspace() else {
+            return Ok(SubmissionResult::error(
+                "Heartbeat requires a workspace (database must be connected).",
+            ));
+        };
+
+        let runner = crate::agent::HeartbeatRunner::new(
+            crate::agent::HeartbeatConfig::default(),
+            crate::workspace::hygiene::HygieneConfig::default(),
+            workspace.clone(),
+            self.llm().clone(),
+            self.safety().clone(),
+        );
+
+        match runner.check_heartbeat().await {
+            crate::agent::HeartbeatResult::Ok => Ok(SubmissionResult::ok_with_message(
+                "Heartbeat: all clear, nothing needs attention.",
+            )),
+            crate::agent::HeartbeatResult::NeedsAttention(msg) => Ok(SubmissionResult::response(
+                format!("Heartbeat findings:\n\n{}", msg),
+            )),
+            crate::agent::HeartbeatResult::Skipped => Ok(SubmissionResult::ok_with_message(
+                "Heartbeat skipped: no HEARTBEAT.md checklist found in workspace.",
+            )),
+            crate::agent::HeartbeatResult::Failed(err) => Ok(SubmissionResult::error(format!(
+                "Heartbeat failed: {}",
+                err
+            ))),
+        }
+    }
+
+    /// Summarize the current thread's conversation.
+    pub(super) async fn process_summarize(
+        &self,
+        session: Arc<Mutex<Session>>,
+        thread_id: Uuid,
+    ) -> Result<SubmissionResult, Error> {
+        let messages = {
+            let sess = session.lock().await;
+            let thread = sess
+                .threads
+                .get(&thread_id)
+                .ok_or_else(|| Error::from(crate::error::JobError::NotFound { id: thread_id }))?;
+            thread.messages()
+        };
+
+        if messages.is_empty() {
+            return Ok(SubmissionResult::ok_with_message(
+                "Nothing to summarize (empty thread).",
+            ));
+        }
+
+        // Build a summary prompt with the conversation
+        let mut context = Vec::new();
+        context.push(ChatMessage::system(
+            "Summarize the conversation so far in 3-5 concise bullet points. \
+             Focus on decisions made, actions taken, and key outcomes. \
+             Be brief and factual.",
+        ));
+        // Include the conversation messages (truncate to last 20 to avoid context overflow)
+        let start = if messages.len() > 20 {
+            messages.len() - 20
+        } else {
+            0
+        };
+        context.extend_from_slice(&messages[start..]);
+        context.push(ChatMessage::user("Summarize this conversation."));
+
+        let request = crate::llm::CompletionRequest::new(context)
+            .with_max_tokens(512)
+            .with_temperature(0.3);
+
+        let reasoning = Reasoning::new(self.llm().clone(), self.safety().clone());
+        match reasoning.complete(request).await {
+            Ok((text, _usage)) => Ok(SubmissionResult::response(format!(
+                "Thread Summary:\n\n{}",
+                text.trim()
+            ))),
+            Err(e) => Ok(SubmissionResult::error(format!("Summarize failed: {}", e))),
+        }
+    }
+
+    /// Suggest next steps based on the current thread.
+    pub(super) async fn process_suggest(
+        &self,
+        session: Arc<Mutex<Session>>,
+        thread_id: Uuid,
+    ) -> Result<SubmissionResult, Error> {
+        let messages = {
+            let sess = session.lock().await;
+            let thread = sess
+                .threads
+                .get(&thread_id)
+                .ok_or_else(|| Error::from(crate::error::JobError::NotFound { id: thread_id }))?;
+            thread.messages()
+        };
+
+        if messages.is_empty() {
+            return Ok(SubmissionResult::ok_with_message(
+                "Nothing to suggest from (empty thread).",
+            ));
+        }
+
+        let mut context = Vec::new();
+        context.push(ChatMessage::system(
+            "Based on the conversation so far, suggest 2-4 concrete next steps the user could take. \
+             Be actionable and specific. Format as a numbered list.",
+        ));
+        let start = if messages.len() > 20 {
+            messages.len() - 20
+        } else {
+            0
+        };
+        context.extend_from_slice(&messages[start..]);
+        context.push(ChatMessage::user("What should I do next?"));
+
+        let request = crate::llm::CompletionRequest::new(context)
+            .with_max_tokens(512)
+            .with_temperature(0.5);
+
+        let reasoning = Reasoning::new(self.llm().clone(), self.safety().clone());
+        match reasoning.complete(request).await {
+            Ok((text, _usage)) => Ok(SubmissionResult::response(format!(
+                "Suggested Next Steps:\n\n{}",
+                text.trim()
+            ))),
+            Err(e) => Ok(SubmissionResult::error(format!("Suggest failed: {}", e))),
+        }
+    }
+
+    /// Handle system commands that bypass thread-state checks entirely.
+    pub(super) async fn handle_system_command(
+        &self,
+        command: &str,
+        args: &[String],
+    ) -> Result<SubmissionResult, Error> {
+        match command {
+            "help" => Ok(SubmissionResult::response(concat!(
+                "System:\n",
+                "  /help             Show this help\n",
+                "  /model [name]     Show or switch the active model\n",
+                "  /version          Show version info\n",
+                "  /tools            List available tools\n",
+                "  /debug            Toggle debug mode\n",
+                "  /ping             Connectivity check\n",
+                "\n",
+                "Jobs:\n",
+                "  /job <desc>       Create a new job\n",
+                "  /status [id]      Check job status\n",
+                "  /cancel <id>      Cancel a job\n",
+                "  /list             List all jobs\n",
+                "\n",
+                "Session:\n",
+                "  /undo             Undo last turn\n",
+                "  /redo             Redo undone turn\n",
+                "  /compact          Compress context window\n",
+                "  /clear            Clear current thread\n",
+                "  /interrupt        Stop current operation\n",
+                "  /new              New conversation thread\n",
+                "  /thread <id>      Switch to thread\n",
+                "  /resume <id>      Resume from checkpoint\n",
+                "\n",
+                "Agent:\n",
+                "  /heartbeat        Run heartbeat check\n",
+                "  /summarize        Summarize current thread\n",
+                "  /suggest          Suggest next steps\n",
+                "\n",
+                "  /quit             Exit",
+            ))),
+
+            "ping" => Ok(SubmissionResult::response("pong!")),
+
+            "version" => Ok(SubmissionResult::response(format!(
+                "{} v{}",
+                env!("CARGO_PKG_NAME"),
+                env!("CARGO_PKG_VERSION")
+            ))),
+
+            "tools" => {
+                let tools = self.tools().list().await;
+                Ok(SubmissionResult::response(format!(
+                    "Available tools: {}",
+                    tools.join(", ")
+                )))
+            }
+
+            "debug" => {
+                // Debug toggle is handled client-side in the REPL.
+                // For non-REPL channels, just acknowledge.
+                Ok(SubmissionResult::ok_with_message(
+                    "Debug toggle is handled by your client.",
+                ))
+            }
+
+            "model" => {
+                let current = self.llm().active_model_name();
+
+                if args.is_empty() {
+                    // Show current model and list available models
+                    let mut out = format!("Active model: {}\n", current);
+                    match self.llm().list_models().await {
+                        Ok(models) if !models.is_empty() => {
+                            out.push_str("\nAvailable models:\n");
+                            for m in &models {
+                                let marker = if *m == current { " (active)" } else { "" };
+                                out.push_str(&format!("  {}{}\n", m, marker));
+                            }
+                            out.push_str("\nUse /model <name> to switch.");
+                        }
+                        Ok(_) => {
+                            out.push_str(
+                                "\nCould not fetch model list. Use /model <name> to switch.",
+                            );
+                        }
+                        Err(e) => {
+                            out.push_str(&format!(
+                                "\nCould not fetch models: {}. Use /model <name> to switch.",
+                                e
+                            ));
+                        }
+                    }
+                    Ok(SubmissionResult::response(out))
+                } else {
+                    let requested = &args[0];
+
+                    // Validate the model exists
+                    match self.llm().list_models().await {
+                        Ok(models) if !models.is_empty() => {
+                            if !models.iter().any(|m| m == requested) {
+                                return Ok(SubmissionResult::error(format!(
+                                    "Unknown model: {}. Available models:\n  {}",
+                                    requested,
+                                    models.join("\n  ")
+                                )));
+                            }
+                        }
+                        Ok(_) => {
+                            // Empty model list, can't validate but try anyway
+                        }
+                        Err(e) => {
+                            tracing::warn!("Could not fetch model list for validation: {}", e);
+                        }
+                    }
+
+                    match self.llm().set_model(requested) {
+                        Ok(()) => Ok(SubmissionResult::response(format!(
+                            "Switched model to: {}",
+                            requested
+                        ))),
+                        Err(e) => Ok(SubmissionResult::error(format!(
+                            "Failed to switch model: {}",
+                            e
+                        ))),
+                    }
+                }
+            }
+
+            _ => Ok(SubmissionResult::error(format!(
+                "Unknown command: {}. Try /help",
+                command
+            ))),
+        }
+    }
+
+    /// Handle legacy command routing from the Router (job commands that go through
+    /// process_user_input -> router -> handle_job_or_command -> here).
+    pub(super) async fn handle_command(
+        &self,
+        command: &str,
+        args: &[String],
+    ) -> Result<Option<String>, Error> {
+        // System commands are now handled directly via Submission::SystemCommand,
+        // but the router may still send us unknown /commands.
+        match self.handle_system_command(command, args).await? {
+            SubmissionResult::Response { content } => Ok(Some(content)),
+            SubmissionResult::Ok { message } => Ok(message),
+            SubmissionResult::Error { message } => Ok(Some(format!("Error: {}", message))),
+            _ => Ok(None),
+        }
+    }
+}

src/agent/compaction.rs

@@ -12,7 +12,8 @@ use chrono::Utc;
 use crate::agent::context_monitor::{CompactionStrategy, ContextBreakdown};
 use crate::agent::session::Thread;
 use crate::error::Error;
-use crate::llm::{ChatMessage, CompletionRequest, LlmProvider};
+use crate::llm::{ChatMessage, CompletionRequest, LlmProvider, Reasoning};
+use crate::safety::SafetyLayer;
 use crate::workspace::Workspace;
 
 /// Result of a compaction operation.
@@ -33,12 +34,13 @@ pub struct CompactionResult {
 /// Compacts conversation context to stay within limits.
 pub struct ContextCompactor {
     llm: Arc<dyn LlmProvider>,
+    safety: Arc<SafetyLayer>,
 }
 
 impl ContextCompactor {
     /// Create a new context compactor.
-    pub fn new(llm: Arc<dyn LlmProvider>) -> Self {
-        Self { llm }
+    pub fn new(llm: Arc<dyn LlmProvider>, safety: Arc<SafetyLayer>) -> Self {
+        Self { llm, safety }
     }
 
     /// Compact a thread's context using the given strategy.
@@ -105,7 +107,16 @@ impl ContextCompactor {
 
         // Write to workspace if available
         let summary_written = if let Some(ws) = workspace {
-            self.write_summary_to_workspace(ws, &summary).await.is_ok()
+            match self.write_summary_to_workspace(ws, &summary).await {
+                Ok(()) => true,
+                Err(e) => {
+                    tracing::warn!(
+                        "Compaction summary write failed (turns will still be truncated): {}",
+                        e
+                    );
+                    false
+                }
+            }
         } else {
             false
         };
@@ -157,7 +168,16 @@ impl ContextCompactor {
         let content = format_turns_for_storage(old_turns);
 
         // Write to workspace
-        let written = self.write_context_to_workspace(ws, &content).await.is_ok();
+        let written = match self.write_context_to_workspace(ws, &content).await {
+            Ok(()) => true,
+            Err(e) => {
+                tracing::warn!(
+                    "Compaction context write failed (turns will still be truncated): {}",
+                    e
+                );
+                false
+            }
+        };
 
         // Truncate
         thread.truncate_turns(keep_recent);
@@ -213,8 +233,9 @@ Be brief but capture all important details. Use bullet points."#,
             .with_max_tokens(1024)
             .with_temperature(0.3);
 
-        let response = self.llm.complete(request).await?;
-        Ok(response.content)
+        let reasoning = Reasoning::new(self.llm.clone(), self.safety.clone());
+        let (text, _) = reasoning.complete(request).await?;
+        Ok(text)
     }
 
     /// Write a summary to the workspace daily log.

src/agent/cost_guard.rs

@@ -0,0 +1,339 @@
+//! Cost enforcement guardrails for the agent.
+//!
+//! Tracks LLM spending and action rates, enforcing configurable limits
+//! to prevent runaway agents from burning through API credits. Especially
+//! important for daemon/heartbeat modes where the agent acts autonomously.
+
+use std::collections::VecDeque;
+use std::sync::atomic::{AtomicBool, Ordering};
+use std::time::Instant;
+
+use rust_decimal::Decimal;
+use rust_decimal_macros::dec;
+use tokio::sync::Mutex;
+
+use crate::llm::costs;
+
+/// Configuration for cost guardrails.
+#[derive(Debug, Clone, Default)]
+pub struct CostGuardConfig {
+    /// Maximum spend per day in cents (e.g. 10000 = $100). None = unlimited.
+    pub max_cost_per_day_cents: Option<u64>,
+    /// Maximum LLM calls per hour. None = unlimited.
+    pub max_actions_per_hour: Option<u64>,
+}
+
+/// Error returned when a cost limit is exceeded.
+#[derive(Debug, Clone)]
+pub enum CostLimitExceeded {
+    /// Daily spending cap reached.
+    DailyBudget { spent_cents: u64, limit_cents: u64 },
+    /// Hourly action rate limit reached.
+    HourlyRate { actions: u64, limit: u64 },
+}
+
+impl std::fmt::Display for CostLimitExceeded {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        match self {
+            Self::DailyBudget {
+                spent_cents,
+                limit_cents,
+            } => write!(
+                f,
+                "Daily cost limit exceeded: spent ${:.2} of ${:.2} allowed",
+                *spent_cents as f64 / 100.0,
+                *limit_cents as f64 / 100.0
+            ),
+            Self::HourlyRate { actions, limit } => write!(
+                f,
+                "Hourly action limit exceeded: {} actions of {} allowed per hour",
+                actions, limit
+            ),
+        }
+    }
+}
+
+/// Tracks costs and action rates, enforcing configurable limits.
+///
+/// Thread-safe; designed to be shared via `Arc<CostGuard>`.
+pub struct CostGuard {
+    config: CostGuardConfig,
+
+    /// Running cost total for the current day (in USD, not cents).
+    daily_cost: Mutex<DailyCost>,
+
+    /// Sliding window of action timestamps for rate limiting.
+    action_window: Mutex<VecDeque<Instant>>,
+
+    /// Flag set when daily budget is exceeded to short-circuit checks.
+    budget_exceeded: AtomicBool,
+}
+
+struct DailyCost {
+    total: Decimal,
+    /// Day boundary (midnight UTC) for resetting the counter.
+    reset_date: chrono::NaiveDate,
+}
+
+impl CostGuard {
+    pub fn new(config: CostGuardConfig) -> Self {
+        Self {
+            config,
+            daily_cost: Mutex::new(DailyCost {
+                total: Decimal::ZERO,
+                reset_date: chrono::Utc::now().date_naive(),
+            }),
+            action_window: Mutex::new(VecDeque::new()),
+            budget_exceeded: AtomicBool::new(false),
+        }
+    }
+
+    /// Check whether the next action is allowed under the configured limits.
+    ///
+    /// Call this BEFORE making an LLM call. Does NOT record the action yet,
+    /// call `record_action` after the action completes.
+    pub async fn check_allowed(&self) -> Result<(), CostLimitExceeded> {
+        // Fast path: if budget already blown, skip the lock
+        if self.budget_exceeded.load(Ordering::Relaxed) {
+            let daily = self.daily_cost.lock().await;
+            let spent_cents = to_cents(daily.total);
+            return Err(CostLimitExceeded::DailyBudget {
+                spent_cents,
+                limit_cents: self.config.max_cost_per_day_cents.unwrap_or(0),
+            });
+        }
+
+        // Check daily budget
+        if let Some(limit_cents) = self.config.max_cost_per_day_cents {
+            let daily = self.daily_cost.lock().await;
+            let spent_cents = to_cents(daily.total);
+            if spent_cents >= limit_cents {
+                self.budget_exceeded.store(true, Ordering::Relaxed);
+                return Err(CostLimitExceeded::DailyBudget {
+                    spent_cents,
+                    limit_cents,
+                });
+            }
+        }
+
+        // Check hourly rate
+        if let Some(limit) = self.config.max_actions_per_hour {
+            let mut window = self.action_window.lock().await;
+            let cutoff = Instant::now() - std::time::Duration::from_secs(3600);
+            // Drain expired entries
+            while window.front().is_some_and(|t| *t < cutoff) {
+                window.pop_front();
+            }
+            let count = window.len() as u64;
+            if count >= limit {
+                return Err(CostLimitExceeded::HourlyRate {
+                    actions: count,
+                    limit,
+                });
+            }
+        }
+
+        Ok(())
+    }
+
+    /// Record a completed LLM action: its token costs and the action timestamp.
+    ///
+    /// Call this AFTER an LLM call completes so that costs are tracked.
+    pub async fn record_llm_call(
+        &self,
+        model: &str,
+        input_tokens: u32,
+        output_tokens: u32,
+    ) -> Decimal {
+        let (input_rate, output_rate) =
+            costs::model_cost(model).unwrap_or_else(costs::default_cost);
+        let cost =
+            input_rate * Decimal::from(input_tokens) + output_rate * Decimal::from(output_tokens);
+
+        // Update daily cost (reset if new day)
+        {
+            let mut daily = self.daily_cost.lock().await;
+            let today = chrono::Utc::now().date_naive();
+            if today != daily.reset_date {
+                daily.total = Decimal::ZERO;
+                daily.reset_date = today;
+                self.budget_exceeded.store(false, Ordering::Relaxed);
+                tracing::info!("Cost guard: daily counter reset for {}", today);
+            }
+            daily.total += cost;
+
+            // Check if we just crossed the threshold
+            if let Some(limit_cents) = self.config.max_cost_per_day_cents {
+                let spent_cents = to_cents(daily.total);
+                if spent_cents >= limit_cents {
+                    self.budget_exceeded.store(true, Ordering::Relaxed);
+                    tracing::warn!(
+                        "Daily cost limit reached: ${:.2} of ${:.2}",
+                        daily.total,
+                        Decimal::from(limit_cents) / dec!(100)
+                    );
+                }
+                // Warn at 80% threshold
+                let warn_threshold = limit_cents * 80 / 100;
+                if spent_cents >= warn_threshold && spent_cents < limit_cents {
+                    tracing::warn!(
+                        "Approaching daily cost limit: ${:.2} of ${:.2} ({}%)",
+                        daily.total,
+                        Decimal::from(limit_cents) / dec!(100),
+                        spent_cents * 100 / limit_cents
+                    );
+                }
+            }
+        }
+
+        // Record action in sliding window
+        {
+            let mut window = self.action_window.lock().await;
+            window.push_back(Instant::now());
+        }
+
+        cost
+    }
+
+    /// Current daily spend in USD (as Decimal).
+    pub async fn daily_spend(&self) -> Decimal {
+        let daily = self.daily_cost.lock().await;
+        let today = chrono::Utc::now().date_naive();
+        if today != daily.reset_date {
+            Decimal::ZERO
+        } else {
+            daily.total
+        }
+    }
+
+    /// Number of actions in the current hourly window.
+    pub async fn actions_this_hour(&self) -> u64 {
+        let mut window = self.action_window.lock().await;
+        let cutoff = Instant::now() - std::time::Duration::from_secs(3600);
+        while window.front().is_some_and(|t| *t < cutoff) {
+            window.pop_front();
+        }
+        window.len() as u64
+    }
+}
+
+/// Convert a Decimal USD amount to whole cents (truncated).
+fn to_cents(usd: Decimal) -> u64 {
+    let cents = (usd * dec!(100)).trunc();
+    cents.to_string().parse::<u64>().unwrap_or(0)
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[tokio::test]
+    async fn test_unlimited_allows_everything() {
+        let guard = CostGuard::new(CostGuardConfig::default());
+
+        // No limits set, should always be allowed
+        assert!(guard.check_allowed().await.is_ok());
+
+        // Record a big call, still allowed
+        guard.record_llm_call("gpt-4o", 100_000, 100_000).await;
+        assert!(guard.check_allowed().await.is_ok());
+    }
+
+    #[tokio::test]
+    async fn test_daily_budget_enforcement() {
+        let guard = CostGuard::new(CostGuardConfig {
+            max_cost_per_day_cents: Some(1), // $0.01 limit
+            max_actions_per_hour: None,
+        });
+
+        // First call allowed
+        assert!(guard.check_allowed().await.is_ok());
+
+        // Record a call that costs more than $0.01
+        // gpt-4o: input=$0.0000025/tok, output=$0.00001/tok
+        // 10000 input + 10000 output = $0.025 + $0.10 = $0.125
+        guard.record_llm_call("gpt-4o", 10_000, 10_000).await;
+
+        // Now should be blocked
+        let result = guard.check_allowed().await;
+        assert!(result.is_err());
+        match result.unwrap_err() {
+            CostLimitExceeded::DailyBudget { limit_cents, .. } => {
+                assert_eq!(limit_cents, 1);
+            }
+            other => panic!("Expected DailyBudget, got {:?}", other),
+        }
+    }
+
+    #[tokio::test]
+    async fn test_hourly_rate_enforcement() {
+        let guard = CostGuard::new(CostGuardConfig {
+            max_cost_per_day_cents: None,
+            max_actions_per_hour: Some(3),
+        });
+
+        // First 3 actions allowed
+        for _ in 0..3 {
+            assert!(guard.check_allowed().await.is_ok());
+            guard.record_llm_call("gpt-4o", 10, 10).await;
+        }
+
+        // 4th should be blocked
+        let result = guard.check_allowed().await;
+        assert!(result.is_err());
+        match result.unwrap_err() {
+            CostLimitExceeded::HourlyRate { actions, limit } => {
+                assert_eq!(actions, 3);
+                assert_eq!(limit, 3);
+            }
+            other => panic!("Expected HourlyRate, got {:?}", other),
+        }
+    }
+
+    #[tokio::test]
+    async fn test_daily_spend_tracking() {
+        let guard = CostGuard::new(CostGuardConfig::default());
+
+        assert_eq!(guard.daily_spend().await, Decimal::ZERO);
+
+        let cost = guard.record_llm_call("gpt-4o", 1000, 500).await;
+        assert!(cost > Decimal::ZERO);
+        assert_eq!(guard.daily_spend().await, cost);
+    }
+
+    #[tokio::test]
+    async fn test_actions_this_hour() {
+        let guard = CostGuard::new(CostGuardConfig::default());
+
+        assert_eq!(guard.actions_this_hour().await, 0);
+
+        guard.record_llm_call("gpt-4o", 10, 10).await;
+        guard.record_llm_call("gpt-4o", 10, 10).await;
+
+        assert_eq!(guard.actions_this_hour().await, 2);
+    }
+
+    #[test]
+    fn test_to_cents() {
+        assert_eq!(to_cents(dec!(1.50)), 150);
+        assert_eq!(to_cents(dec!(0.01)), 1);
+        assert_eq!(to_cents(Decimal::ZERO), 0);
+    }
+
+    #[test]
+    fn test_cost_limit_display() {
+        let budget = CostLimitExceeded::DailyBudget {
+            spent_cents: 1050,
+            limit_cents: 1000,
+        };
+        assert!(budget.to_string().contains("$10.50"));
+        assert!(budget.to_string().contains("$10.00"));
+
+        let rate = CostLimitExceeded::HourlyRate {
+            actions: 101,
+            limit: 100,
+        };
+        assert!(rate.to_string().contains("101 actions"));
+        assert!(rate.to_string().contains("100 allowed"));
+    }
+}

src/agent/heartbeat.rs

@@ -29,8 +29,10 @@ use std::time::Duration;
 use tokio::sync::mpsc;
 
 use crate::channels::OutgoingResponse;
-use crate::llm::{ChatMessage, CompletionRequest, FinishReason, LlmProvider};
+use crate::llm::{ChatMessage, CompletionRequest, LlmProvider, Reasoning};
+use crate::safety::SafetyLayer;
 use crate::workspace::Workspace;
+use crate::workspace::hygiene::HygieneConfig;
 
 /// Configuration for the heartbeat runner.
 #[derive(Debug, Clone)]
@@ -96,8 +98,10 @@ pub enum HeartbeatResult {
 /// Heartbeat runner for proactive periodic execution.
 pub struct HeartbeatRunner {
     config: HeartbeatConfig,
+    hygiene_config: HygieneConfig,
     workspace: Arc<Workspace>,
     llm: Arc<dyn LlmProvider>,
+    safety: Arc<SafetyLayer>,
     response_tx: Option<mpsc::Sender<OutgoingResponse>>,
     consecutive_failures: u32,
 }
@@ -106,13 +110,17 @@ impl HeartbeatRunner {
     /// Create a new heartbeat runner.
     pub fn new(
         config: HeartbeatConfig,
+        hygiene_config: HygieneConfig,
         workspace: Arc<Workspace>,
         llm: Arc<dyn LlmProvider>,
+        safety: Arc<SafetyLayer>,
     ) -> Self {
         Self {
             config,
+            hygiene_config,
             workspace,
             llm,
+            safety,
             response_tx: None,
             consecutive_failures: 0,
         }
@@ -145,6 +153,22 @@ impl HeartbeatRunner {
         loop {
             interval.tick().await;
 
+            // Run memory hygiene in the background so it never delays the
+            // heartbeat checklist. Failures are logged inside run_if_due.
+            let hygiene_workspace = Arc::clone(&self.workspace);
+            let hygiene_config = self.hygiene_config.clone();
+            tokio::spawn(async move {
+                let report =
+                    crate::workspace::hygiene::run_if_due(&hygiene_workspace, &hygiene_config)
+                        .await;
+                if report.had_work() {
+                    tracing::info!(
+                        daily_logs_deleted = report.daily_logs_deleted,
+                        "heartbeat: memory hygiene deleted stale documents"
+                    );
+                }
+            });
+
             match self.check_heartbeat().await {
                 HeartbeatResult::Ok => {
                     tracing::debug!("Heartbeat OK");
@@ -238,25 +262,18 @@ impl HeartbeatRunner {
             .with_max_tokens(max_tokens)
             .with_temperature(0.3);
 
-        let response = match self.llm.complete(request).await {
+        let reasoning = Reasoning::new(self.llm.clone(), self.safety.clone());
+        let (content, _usage) = match reasoning.complete(request).await {
             Ok(r) => r,
             Err(e) => return HeartbeatResult::Failed(format!("LLM call failed: {}", e)),
         };
 
-        let content = response.content.trim();
+        let content = content.trim();
 
         // Guard against empty content. Reasoning models (e.g. GLM-4.7) may
         // burn all output tokens on chain-of-thought and return content: null.
         if content.is_empty() {
-            return if response.finish_reason == FinishReason::Length {
-                HeartbeatResult::Failed(
-                    "LLM response was truncated (finish_reason=length) with no content. \
-                     The model may have exhausted its token budget on reasoning."
-                        .to_string(),
-                )
-            } else {
-                HeartbeatResult::Failed("LLM returned empty content.".to_string())
-            };
+            return HeartbeatResult::Failed("LLM returned empty content.".to_string());
         }
 
         // Check if nothing needs attention
@@ -332,11 +349,13 @@ fn strip_html_comments(content: &str) -> String {
 /// Returns a handle that can be used to stop the runner.
 pub fn spawn_heartbeat(
     config: HeartbeatConfig,
+    hygiene_config: HygieneConfig,
     workspace: Arc<Workspace>,
     llm: Arc<dyn LlmProvider>,
+    safety: Arc<SafetyLayer>,
     response_tx: Option<mpsc::Sender<OutgoingResponse>>,
 ) -> tokio::task::JoinHandle<()> {
-    let mut runner = HeartbeatRunner::new(config, workspace, llm);
+    let mut runner = HeartbeatRunner::new(config, hygiene_config, workspace, llm, safety);
     if let Some(tx) = response_tx {
         runner = runner.with_response_channel(tx);
     }

src/agent/job_monitor.rs

@@ -0,0 +1,245 @@
+//! Background job monitor that forwards Claude Code output to the main agent loop.
+//!
+//! When the main agent kicks off a sandbox job (especially Claude Code), this
+//! monitor subscribes to the broadcast event channel and injects relevant
+//! assistant messages back into the channel manager's stream. This lets the
+//! main agent see what the sub-agent is producing and surface it to the user.
+//!
+//! ```text
+//!   Container ──NDJSON──► Orchestrator ──broadcast──► JobMonitor
+//!                                                        │
+//!                                                  inject_tx (mpsc)
+//!                                                        │
+//!                                                        ▼
+//!                                                   Agent Loop
+//! ```
+
+use tokio::sync::{broadcast, mpsc};
+use tokio::task::JoinHandle;
+use uuid::Uuid;
+
+use crate::channels::IncomingMessage;
+use crate::channels::web::types::SseEvent;
+
+/// Spawn a background task that watches for events from a specific job and
+/// injects assistant messages into the agent loop.
+///
+/// The monitor forwards:
+/// - `SseEvent::JobMessage` (assistant role): injected as incoming messages so
+///   the main agent can read and relay to the user.
+/// - `SseEvent::JobResult`: injected as a completion notice, then the task exits.
+///
+/// Tool use/result and status events are intentionally skipped (too noisy for
+/// the main agent's context window).
+pub fn spawn_job_monitor(
+    job_id: Uuid,
+    mut event_rx: broadcast::Receiver<(Uuid, SseEvent)>,
+    inject_tx: mpsc::Sender<IncomingMessage>,
+) -> JoinHandle<()> {
+    let short_id = job_id.to_string()[..8].to_string();
+
+    tokio::spawn(async move {
+        tracing::info!(job_id = %short_id, "Job monitor started successfully");
+
+        loop {
+            match event_rx.recv().await {
+                Ok((ev_job_id, event)) => {
+                    if ev_job_id != job_id {
+                        continue;
+                    }
+
+                    match event {
+                        SseEvent::JobMessage { role, content, .. } if role == "assistant" => {
+                            let msg = IncomingMessage::new(
+                                "job_monitor",
+                                "system",
+                                format!("[Job {}] Claude Code: {}", short_id, content),
+                            );
+                            if inject_tx.send(msg).await.is_err() {
+                                tracing::debug!(
+                                    job_id = %short_id,
+                                    "Inject channel closed, stopping monitor"
+                                );
+                                break;
+                            }
+                        }
+                        SseEvent::JobResult { status, .. } => {
+                            let msg = IncomingMessage::new(
+                                "job_monitor",
+                                "system",
+                                format!(
+                                    "[Job {}] Container finished (status: {})",
+                                    short_id, status
+                                ),
+                            );
+                            let _ = inject_tx.send(msg).await;
+                            tracing::debug!(
+                                job_id = %short_id,
+                                status = %status,
+                                "Job monitor exiting (job finished)"
+                            );
+                            break;
+                        }
+                        _ => {
+                            // Skip tool_use, tool_result, status events
+                        }
+                    }
+                }
+                Err(broadcast::error::RecvError::Lagged(n)) => {
+                    tracing::warn!(
+                        job_id = %short_id,
+                        skipped = n,
+                        "Job monitor lagged, some events were dropped"
+                    );
+                }
+                Err(broadcast::error::RecvError::Closed) => {
+                    tracing::debug!(
+                        job_id = %short_id,
+                        "Broadcast channel closed, stopping monitor"
+                    );
+                    break;
+                }
+            }
+        }
+    })
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[tokio::test]
+    async fn test_monitor_forwards_assistant_messages() {
+        let (event_tx, _) = broadcast::channel::<(Uuid, SseEvent)>(16);
+        let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);
+
+        let job_id = Uuid::new_v4();
+        let _handle = spawn_job_monitor(job_id, event_tx.subscribe(), inject_tx);
+
+        // Send an assistant message
+        event_tx
+            .send((
+                job_id,
+                SseEvent::JobMessage {
+                    job_id: job_id.to_string(),
+                    role: "assistant".to_string(),
+                    content: "I found a bug".to_string(),
+                },
+            ))
+            .unwrap();
+
+        let msg = tokio::time::timeout(std::time::Duration::from_secs(1), inject_rx.recv())
+            .await
+            .unwrap()
+            .unwrap();
+
+        assert_eq!(msg.channel, "job_monitor");
+        assert_eq!(msg.user_id, "system");
+        assert!(msg.content.contains("I found a bug"));
+    }
+
+    #[tokio::test]
+    async fn test_monitor_ignores_other_jobs() {
+        let (event_tx, _) = broadcast::channel::<(Uuid, SseEvent)>(16);
+        let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);
+
+        let job_id = Uuid::new_v4();
+        let other_job_id = Uuid::new_v4();
+        let _handle = spawn_job_monitor(job_id, event_tx.subscribe(), inject_tx);
+
+        // Send a message for a different job
+        event_tx
+            .send((
+                other_job_id,
+                SseEvent::JobMessage {
+                    job_id: other_job_id.to_string(),
+                    role: "assistant".to_string(),
+                    content: "wrong job".to_string(),
+                },
+            ))
+            .unwrap();
+
+        // Should not receive anything
+        let result =
+            tokio::time::timeout(std::time::Duration::from_millis(100), inject_rx.recv()).await;
+        assert!(
+            result.is_err(),
+            "should have timed out, no message expected"
+        );
+    }
+
+    #[tokio::test]
+    async fn test_monitor_exits_on_job_result() {
+        let (event_tx, _) = broadcast::channel::<(Uuid, SseEvent)>(16);
+        let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);
+
+        let job_id = Uuid::new_v4();
+        let handle = spawn_job_monitor(job_id, event_tx.subscribe(), inject_tx);
+
+        // Send a completion event
+        event_tx
+            .send((
+                job_id,
+                SseEvent::JobResult {
+                    job_id: job_id.to_string(),
+                    status: "completed".to_string(),
+                    session_id: None,
+                },
+            ))
+            .unwrap();
+
+        // Should receive the completion message
+        let msg = tokio::time::timeout(std::time::Duration::from_secs(1), inject_rx.recv())
+            .await
+            .unwrap()
+            .unwrap();
+        assert!(msg.content.contains("finished"));
+
+        // The monitor task should exit
+        tokio::time::timeout(std::time::Duration::from_secs(1), handle)
+            .await
+            .expect("monitor should have exited")
+            .expect("monitor task should not panic");
+    }
+
+    #[tokio::test]
+    async fn test_monitor_skips_tool_events() {
+        let (event_tx, _) = broadcast::channel::<(Uuid, SseEvent)>(16);
+        let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);
+
+        let job_id = Uuid::new_v4();
+        let _handle = spawn_job_monitor(job_id, event_tx.subscribe(), inject_tx);
+
+        // Send tool use event (should be skipped)
+        event_tx
+            .send((
+                job_id,
+                SseEvent::JobToolUse {
+                    job_id: job_id.to_string(),
+                    tool_name: "shell".to_string(),
+                    input: serde_json::json!({"command": "ls"}),
+                },
+            ))
+            .unwrap();
+
+        // Send user message (should be skipped)
+        event_tx
+            .send((
+                job_id,
+                SseEvent::JobMessage {
+                    job_id: job_id.to_string(),
+                    role: "user".to_string(),
+                    content: "user prompt".to_string(),
+                },
+            ))
+            .unwrap();
+
+        // Should not receive anything for tool events or user messages
+        let result =
+            tokio::time::timeout(std::time::Duration::from_millis(100), inject_rx.recv()).await;
+        assert!(
+            result.is_err(),
+            "should have timed out, no message expected"
+        );
+    }
+}

src/agent/mod.rs

@@ -11,9 +11,13 @@
 //! - Context compaction for long conversations
 
 mod agent_loop;
+mod commands;
 pub mod compaction;
 pub mod context_monitor;
+pub mod cost_guard;
+mod dispatcher;
 mod heartbeat;
+pub mod job_monitor;
 mod router;
 pub mod routine;
 pub mod routine_engine;
@@ -23,6 +27,7 @@ pub mod session;
 mod session_manager;
 pub mod submission;
 pub mod task;
+mod thread_ops;
 pub mod undo;
 pub mod worker;
 
@@ -39,6 +44,6 @@ pub use self_repair::{BrokenTool, RepairResult, RepairTask, SelfRepair, StuckJob
 pub use session::{PendingApproval, PendingAuth, Session, Thread, ThreadState, Turn, TurnState};
 pub use session_manager::SessionManager;
 pub use submission::{Submission, SubmissionParser, SubmissionResult};
-pub use task::{Task, TaskContext, TaskHandler, TaskOutput, TaskStatus};
+pub use task::{Task, TaskContext, TaskHandler, TaskOutput};
 pub use undo::{Checkpoint, UndoManager};
 pub use worker::{Worker, WorkerDeps};

src/agent/routine.rs

@@ -26,6 +26,8 @@ use chrono::{DateTime, Utc};
 use serde::{Deserialize, Serialize};
 use uuid::Uuid;
 
+use crate::error::RoutineError;
+
 /// A routine is a named, persistent, user-owned task with a trigger and an action.
 #[derive(Debug, Clone, Serialize, Deserialize)]
 pub struct Routine {
@@ -86,13 +88,16 @@ impl Trigger {
     }
 
     /// Parse a trigger from its DB representation.
-    pub fn from_db(trigger_type: &str, config: serde_json::Value) -> Result<Self, String> {
+    pub fn from_db(trigger_type: &str, config: serde_json::Value) -> Result<Self, RoutineError> {
         match trigger_type {
             "cron" => {
                 let schedule = config
                     .get("schedule")
                     .and_then(|v| v.as_str())
-                    .ok_or("cron trigger missing 'schedule'")?
+                    .ok_or_else(|| RoutineError::MissingField {
+                        context: "cron trigger".into(),
+                        field: "schedule".into(),
+                    })?
                     .to_string();
                 Ok(Trigger::Cron { schedule })
             }
@@ -100,7 +105,10 @@ impl Trigger {
                 let pattern = config
                     .get("pattern")
                     .and_then(|v| v.as_str())
-                    .ok_or("event trigger missing 'pattern'")?
+                    .ok_or_else(|| RoutineError::MissingField {
+                        context: "event trigger".into(),
+                        field: "pattern".into(),
+                    })?
                     .to_string();
                 let channel = config
                     .get("channel")
@@ -120,7 +128,9 @@ impl Trigger {
                 Ok(Trigger::Webhook { path, secret })
             }
             "manual" => Ok(Trigger::Manual),
-            other => Err(format!("unknown trigger type: {other}")),
+            other => Err(RoutineError::UnknownTriggerType {
+                trigger_type: other.to_string(),
+            }),
         }
     }
 
@@ -186,13 +196,16 @@ impl RoutineAction {
     }
 
     /// Parse an action from its DB representation.
-    pub fn from_db(action_type: &str, config: serde_json::Value) -> Result<Self, String> {
+    pub fn from_db(action_type: &str, config: serde_json::Value) -> Result<Self, RoutineError> {
         match action_type {
             "lightweight" => {
                 let prompt = config
                     .get("prompt")
                     .and_then(|v| v.as_str())
-                    .ok_or("lightweight action missing 'prompt'")?
+                    .ok_or_else(|| RoutineError::MissingField {
+                        context: "lightweight action".into(),
+                        field: "prompt".into(),
+                    })?
                     .to_string();
                 let context_paths = config
                     .get("context_paths")
@@ -217,12 +230,18 @@ impl RoutineAction {
                 let title = config
                     .get("title")
                     .and_then(|v| v.as_str())
-                    .ok_or("full_job action missing 'title'")?
+                    .ok_or_else(|| RoutineError::MissingField {
+                        context: "full_job action".into(),
+                        field: "title".into(),
+                    })?
                     .to_string();
                 let description = config
                     .get("description")
                     .and_then(|v| v.as_str())
-                    .ok_or("full_job action missing 'description'")?
+                    .ok_or_else(|| RoutineError::MissingField {
+                        context: "full_job action".into(),
+                        field: "description".into(),
+                    })?
                     .to_string();
                 let max_iterations = config
                     .get("max_iterations")
@@ -235,7 +254,9 @@ impl RoutineAction {
                     max_iterations,
                 })
             }
-            other => Err(format!("unknown action type: {other}")),
+            other => Err(RoutineError::UnknownActionType {
+                action_type: other.to_string(),
+            }),
         }
     }
 
@@ -334,14 +355,16 @@ impl std::fmt::Display for RunStatus {
 }
 
 impl FromStr for RunStatus {
-    type Err = String;
+    type Err = RoutineError;
     fn from_str(s: &str) -> Result<Self, Self::Err> {
         match s {
             "running" => Ok(RunStatus::Running),
             "ok" => Ok(RunStatus::Ok),
             "attention" => Ok(RunStatus::Attention),
             "failed" => Ok(RunStatus::Failed),
-            other => Err(format!("unknown run status: {other}")),
+            other => Err(RoutineError::UnknownRunStatus {
+                status: other.to_string(),
+            }),
         }
     }
 }
@@ -370,9 +393,11 @@ pub fn content_hash(content: &str) -> u64 {
 }
 
 /// Parse a cron expression and compute the next fire time from now.
-pub fn next_cron_fire(schedule: &str) -> Result<Option<DateTime<Utc>>, String> {
+pub fn next_cron_fire(schedule: &str) -> Result<Option<DateTime<Utc>>, RoutineError> {
     let cron_schedule =
-        cron::Schedule::from_str(schedule).map_err(|e| format!("invalid cron: {e}"))?;
+        cron::Schedule::from_str(schedule).map_err(|e| RoutineError::InvalidCron {
+            reason: e.to_string(),
+        })?;
     Ok(cron_schedule.upcoming(Utc).next())
 }
 

src/agent/routine_engine.rs

@@ -25,6 +25,7 @@ use crate::agent::routine::{
 use crate::channels::{IncomingMessage, OutgoingResponse};
 use crate::config::RoutineConfig;
 use crate::db::Database;
+use crate::error::RoutineError;
 use crate::llm::{ChatMessage, CompletionRequest, FinishReason, LlmProvider};
 use crate::workspace::Workspace;
 
@@ -174,23 +175,26 @@ impl RoutineEngine {
     }
 
     /// Fire a routine manually (from tool call or CLI).
-    pub async fn fire_manual(&self, routine_id: Uuid) -> Result<Uuid, String> {
+    pub async fn fire_manual(&self, routine_id: Uuid) -> Result<Uuid, RoutineError> {
         let routine = self
             .store
             .get_routine(routine_id)
             .await
-            .map_err(|e| format!("DB error: {e}"))?
-            .ok_or_else(|| format!("routine {routine_id} not found"))?;
+            .map_err(|e| RoutineError::Database {
+                reason: e.to_string(),
+            })?
+            .ok_or(RoutineError::NotFound { id: routine_id })?;
 
         if !routine.enabled {
-            return Err(format!("routine '{}' is disabled", routine.name));
+            return Err(RoutineError::Disabled {
+                name: routine.name.clone(),
+            });
         }
 
         if !self.check_concurrent(&routine).await {
-            return Err(format!(
-                "routine '{}' already at max concurrent runs",
-                routine.name
-            ));
+            return Err(RoutineError::MaxConcurrent {
+                name: routine.name.clone(),
+            });
         }
 
         let run_id = Uuid::new_v4();
@@ -209,7 +213,9 @@ impl RoutineEngine {
         };
 
         if let Err(e) = self.store.create_routine_run(&run).await {
-            return Err(format!("failed to create run record: {e}"));
+            return Err(RoutineError::Database {
+                reason: format!("failed to create run record: {e}"),
+            });
         }
 
         // Execute inline for manual triggers (caller wants to wait)
@@ -313,13 +319,27 @@ async fn execute_routine(ctx: EngineContext, routine: Routine, run: RoutineRun)
             max_tokens,
         } => execute_lightweight(&ctx, &routine, prompt, context_paths, *max_tokens).await,
         RoutineAction::FullJob { description, .. } => {
-            // Full job mode: for now, execute as lightweight with the description
-            // as prompt. Full scheduler integration will come as a follow-up.
-            tracing::info!(
+            // Full job mode: scheduler integration not yet implemented.
+            // Execute as lightweight and prepend a warning to the summary.
+            tracing::warn!(
                 routine = %routine.name,
-                "FullJob mode executing as lightweight (scheduler integration pending)"
+                "FullJob mode not yet implemented; falling back to lightweight execution"
             );
-            execute_lightweight(&ctx, &routine, description, &[], ctx.max_lightweight_tokens).await
+            match execute_lightweight(&ctx, &routine, description, &[], ctx.max_lightweight_tokens)
+                .await
+            {
+                Ok((status, summary, tokens)) => {
+                    let warning = "[Note: FullJob mode is not yet implemented. This routine ran as \
+                         a single LLM call without tool access. Configure as 'lightweight' \
+                         or wait for full scheduler integration.]";
+                    let summary = match summary {
+                        Some(s) => Some(format!("{warning}\n\n{s}")),
+                        None => Some(warning.to_string()),
+                    };
+                    Ok((status, summary, tokens))
+                }
+                Err(e) => Err(e),
+            }
         }
     };
 
@@ -331,7 +351,7 @@ async fn execute_routine(ctx: EngineContext, routine: Routine, run: RoutineRun)
         Ok(execution) => execution,
         Err(e) => {
             tracing::error!(routine = %routine.name, "Execution failed: {}", e);
-            (RunStatus::Failed, Some(e), None)
+            (RunStatus::Failed, Some(e.to_string()), None)
         }
     };
 
@@ -384,6 +404,20 @@ async fn execute_routine(ctx: EngineContext, routine: Routine, run: RoutineRun)
     .await;
 }
 
+/// Sanitize a routine name for use in workspace paths.
+/// Only keeps alphanumeric, dash, and underscore characters; replaces everything else.
+fn sanitize_routine_name(name: &str) -> String {
+    name.chars()
+        .map(|c| {
+            if c.is_ascii_alphanumeric() || c == '-' || c == '_' {
+                c
+            } else {
+                '_'
+            }
+        })
+        .collect()
+}
+
 /// Execute a lightweight routine (single LLM call).
 async fn execute_lightweight(
     ctx: &EngineContext,
@@ -391,7 +425,7 @@ async fn execute_lightweight(
     prompt: &str,
     context_paths: &[String],
     max_tokens: u32,
-) -> Result<(RunStatus, Option<String>, Option<i32>), String> {
+) -> Result<(RunStatus, Option<String>, Option<i32>), RoutineError> {
     // Load context from workspace
     let mut context_parts = Vec::new();
     for path in context_paths {
@@ -408,8 +442,9 @@ async fn execute_lightweight(
         }
     }
 
-    // Load routine state from workspace
-    let state_path = format!("routines/{}/state.md", routine.name);
+    // Load routine state from workspace (name sanitized to prevent path traversal)
+    let safe_name = sanitize_routine_name(&routine.name);
+    let state_path = format!("routines/{safe_name}/state.md");
     let state_content = match ctx.workspace.read(&state_path).await {
         Ok(doc) => Some(doc.content),
         Err(_) => None,
@@ -469,7 +504,9 @@ async fn execute_lightweight(
         .llm
         .complete(request)
         .await
-        .map_err(|e| format!("LLM call failed: {e}"))?;
+        .map_err(|e| RoutineError::LlmFailed {
+            reason: e.to_string(),
+        })?;
 
     let content = response.content.trim();
     let tokens_used = Some((response.input_tokens + response.output_tokens) as i32);
@@ -477,13 +514,9 @@ async fn execute_lightweight(
     // Empty content guard (same as heartbeat)
     if content.is_empty() {
         return if response.finish_reason == FinishReason::Length {
-            Err(
-                "LLM response truncated (finish_reason=length) with no content. \
-                 Model may have exhausted token budget on reasoning."
-                    .to_string(),
-            )
+            Err(RoutineError::TruncatedResponse)
         } else {
-            Err("LLM returned empty content.".to_string())
+            Err(RoutineError::EmptyResponse)
         };
     }
 

src/agent/scheduler.rs

@@ -136,7 +136,9 @@ impl Scheduler {
             });
 
             // Start the worker
-            let _ = tx.send(WorkerMessage::Start).await;
+            if tx.send(WorkerMessage::Start).await.is_err() {
+                tracing::error!(job_id = %job_id, "Worker died before receiving Start message");
+            }
 
             // Insert while still holding the write lock
             jobs.insert(job_id, ScheduledJob { handle, tx });
@@ -418,10 +420,16 @@ impl Scheduler {
             // Update job state
             self.context_manager
                 .update_context(job_id, |ctx| {
-                    let _ = ctx.transition_to(
+                    if let Err(e) = ctx.transition_to(
                         JobState::Cancelled,
                         Some("Stopped by scheduler".to_string()),
-                    );
+                    ) {
+                        tracing::warn!(
+                            job_id = %job_id,
+                            error = %e,
+                            "Failed to transition job to Cancelled state"
+                        );
+                    }
                 })
                 .await?;
 

src/agent/self_repair.rs

@@ -66,12 +66,14 @@ pub trait SelfRepair: Send + Sync {
 /// Default self-repair implementation.
 pub struct DefaultSelfRepair {
     context_manager: Arc<ContextManager>,
-    #[allow(dead_code)] // Will be used for time-based stuck detection
+    // TODO: use for time-based stuck detection (currently only max_repair_attempts is checked)
+    #[allow(dead_code)]
     stuck_threshold: Duration,
     max_repair_attempts: u32,
     store: Option<Arc<dyn Database>>,
     builder: Option<Arc<dyn SoftwareBuilder>>,
-    #[allow(dead_code)] // Will be used for tool hot-reload after repair
+    // TODO: use for tool hot-reload after repair
+    #[allow(dead_code)]
     tools: Option<Arc<ToolRegistry>>,
 }
 
@@ -93,15 +95,15 @@ impl DefaultSelfRepair {
     }
 
     /// Add a Store for tool failure tracking.
-    #[allow(dead_code)] // Public API for configuring repair with persistence
-    pub fn with_store(mut self, store: Arc<dyn Database>) -> Self {
+    #[allow(dead_code)] // TODO: wire up in main.rs when persistence is needed
+    pub(crate) fn with_store(mut self, store: Arc<dyn Database>) -> Self {
         self.store = Some(store);
         self
     }
 
     /// Add a Builder and ToolRegistry for automatic tool repair.
-    #[allow(dead_code)] // Public API for enabling automatic tool repair
-    pub fn with_builder(
+    #[allow(dead_code)] // TODO: wire up in main.rs when auto-repair is needed
+    pub(crate) fn with_builder(
         mut self,
         builder: Arc<dyn SoftwareBuilder>,
         tools: Arc<ToolRegistry>,

src/agent/session.rs

@@ -16,7 +16,7 @@ use chrono::{DateTime, Utc};
 use serde::{Deserialize, Serialize};
 use uuid::Uuid;
 
-use crate::llm::ChatMessage;
+use crate::llm::{ChatMessage, ToolCall};
 
 /// A session containing one or more threads.
 #[derive(Debug, Clone, Serialize, Deserialize)]
@@ -70,10 +70,9 @@ impl Session {
     pub fn create_thread(&mut self) -> &mut Thread {
         let thread = Thread::new(self.id);
         let thread_id = thread.id;
-        self.threads.insert(thread_id, thread);
         self.active_thread = Some(thread_id);
         self.last_active_at = Utc::now();
-        self.threads.get_mut(&thread_id).expect("just inserted")
+        self.threads.entry(thread_id).or_insert(thread)
     }
 
     /// Get the active thread.
@@ -88,10 +87,19 @@ impl Session {
 
     /// Get or create the active thread.
     pub fn get_or_create_thread(&mut self) -> &mut Thread {
-        if self.active_thread.is_none() {
-            self.create_thread();
+        match self.active_thread {
+            None => self.create_thread(),
+            Some(id) => {
+                if self.threads.contains_key(&id) {
+                    // Safe: contains_key confirmed the entry exists.
+                    self.threads.get_mut(&id).unwrap()
+                } else {
+                    // Stale active_thread ID: create a new thread, which
+                    // updates self.active_thread to the new thread's ID.
+                    self.create_thread()
+                }
+            }
         }
-        self.active_thread_mut().expect("just created")
     }
 
     /// Switch to a different thread.
@@ -148,6 +156,10 @@ pub struct PendingApproval {
     pub tool_call_id: String,
     /// Context messages at the time of the request (to resume from).
     pub context_messages: Vec<ChatMessage>,
+    /// Remaining tool calls from the same assistant message that were not
+    /// executed yet when approval was requested.
+    #[serde(default)]
+    pub deferred_tool_calls: Vec<ToolCall>,
 }
 
 /// A conversation thread within a session.
@@ -173,10 +185,6 @@ pub struct Thread {
     /// Pending auth token request (thread is in auth mode).
     #[serde(default)]
     pub pending_auth: Option<PendingAuth>,
-    /// Last NEAR AI response ID for response chaining. Persisted to DB
-    /// metadata so we can resume chaining across restarts.
-    #[serde(default)]
-    pub last_response_id: Option<String>,
 }
 
 impl Thread {
@@ -193,7 +201,6 @@ impl Thread {
             metadata: serde_json::Value::Null,
             pending_approval: None,
             pending_auth: None,
-            last_response_id: None,
         }
     }
 
@@ -210,7 +217,6 @@ impl Thread {
             metadata: serde_json::Value::Null,
             pending_approval: None,
             pending_auth: None,
-            last_response_id: None,
         }
     }
 
@@ -236,7 +242,8 @@ impl Thread {
         self.turns.push(turn);
         self.state = ThreadState::Processing;
         self.updated_at = Utc::now();
-        self.turns.last_mut().expect("just pushed")
+        // turn_number was len() before push, so it's a valid index after push
+        &mut self.turns[turn_number]
     }
 
     /// Complete the current turn with a response.
@@ -349,8 +356,10 @@ impl Thread {
                 if let Some(next) = iter.peek()
                     && next.role == crate::llm::Role::Assistant
                 {
-                    let response = iter.next().expect("peeked");
-                    turn.complete(&response.content);
+                    // iter.next() is guaranteed Some after a successful peek()
+                    if let Some(response) = iter.next() {
+                        turn.complete(&response.content);
+                    }
                 }
 
                 self.turns.push(turn);
@@ -848,7 +857,6 @@ mod tests {
 
         thread.start_turn("hello");
         thread.complete_turn("world");
-        thread.last_response_id = Some("resp_abc123".to_string());
 
         let json = serde_json::to_string(&thread).unwrap();
         let restored: Thread = serde_json::from_str(&json).unwrap();
@@ -858,7 +866,6 @@ mod tests {
         assert_eq!(restored.turns.len(), 1);
         assert_eq!(restored.turns[0].user_input, "hello");
         assert_eq!(restored.turns[0].response, Some("world".to_string()));
-        assert_eq!(restored.last_response_id, Some("resp_abc123".to_string()));
     }
 
     #[test]
@@ -946,6 +953,7 @@ mod tests {
             description: "dangerous command".to_string(),
             tool_call_id: "call_123".to_string(),
             context_messages: vec![ChatMessage::user("do it")],
+            deferred_tool_calls: vec![],
         };
 
         thread.await_approval(approval);
@@ -969,6 +977,7 @@ mod tests {
             description: "test".to_string(),
             tool_call_id: "call_456".to_string(),
             context_messages: vec![],
+            deferred_tool_calls: vec![],
         };
 
         thread.await_approval(approval);

src/agent/session_manager.rs

@@ -13,6 +13,9 @@ use crate::agent::session::Session;
 use crate::agent::undo::UndoManager;
 use crate::hooks::HookRegistry;
 
+/// Warn when session count exceeds this threshold.
+const SESSION_COUNT_WARNING_THRESHOLD: usize = 1000;
+
 /// Key for mapping external thread IDs to internal ones.
 #[derive(Clone, Hash, Eq, PartialEq)]
 struct ThreadKey {
@@ -68,6 +71,14 @@ impl SessionManager {
         let session = Arc::new(Mutex::new(new_session));
         sessions.insert(user_id.to_string(), Arc::clone(&session));
 
+        if sessions.len() >= SESSION_COUNT_WARNING_THRESHOLD && sessions.len() % 100 == 0 {
+            tracing::warn!(
+                "High session count: {} active sessions. \
+                 Pruning runs every 10 minutes; consider reducing session_idle_timeout.",
+                sessions.len()
+            );
+        }
+
         // Fire OnSessionStart hook (fire-and-forget)
         if let Some(ref hooks) = self.hooks {
             let hooks = hooks.clone();

src/agent/submission.rs

@@ -118,19 +118,19 @@ impl SubmissionParser {
         // Approval responses (simple yes/no/always for pending approvals)
         // These are short enough to check explicitly
         match lower.as_str() {
-            "yes" | "y" | "approve" | "ok" => {
+            "yes" | "y" | "approve" | "ok" | "/approve" | "/yes" | "/y" => {
                 return Submission::ApprovalResponse {
                     approved: true,
                     always: false,
                 };
             }
-            "always" | "yes always" | "approve always" => {
+            "always" | "a" | "yes always" | "approve always" | "/always" | "/a" => {
                 return Submission::ApprovalResponse {
                     approved: true,
                     always: true,
                 };
             }
-            "no" | "n" | "deny" | "reject" | "cancel" => {
+            "no" | "n" | "deny" | "reject" | "cancel" | "/deny" | "/no" | "/n" => {
                 return Submission::ApprovalResponse {
                     approved: false,
                     always: false,
@@ -234,6 +234,7 @@ impl Submission {
     }
 
     /// Create an approval submission.
+    #[cfg(test)]
     pub fn approval(request_id: Uuid, approved: bool) -> Self {
         Self::ExecApproval {
             request_id,
@@ -243,6 +244,7 @@ impl Submission {
     }
 
     /// Create an "always approve" submission.
+    #[cfg(test)]
     pub fn always_approve(request_id: Uuid) -> Self {
         Self::ExecApproval {
             request_id,
@@ -252,26 +254,31 @@ impl Submission {
     }
 
     /// Create an interrupt submission.
+    #[cfg(test)]
     pub fn interrupt() -> Self {
         Self::Interrupt
     }
 
     /// Create a compact submission.
+    #[cfg(test)]
     pub fn compact() -> Self {
         Self::Compact
     }
 
     /// Create an undo submission.
+    #[cfg(test)]
     pub fn undo() -> Self {
         Self::Undo
     }
 
     /// Create a redo submission.
+    #[cfg(test)]
     pub fn redo() -> Self {
         Self::Redo
     }
 
     /// Check if this submission starts a new turn.
+    #[cfg(test)]
     pub fn starts_turn(&self) -> bool {
         matches!(self, Self::UserInput { .. })
     }
@@ -340,6 +347,7 @@ impl SubmissionResult {
     }
 
     /// Create an OK result.
+    #[cfg(test)]
     pub fn ok() -> Self {
         Self::Ok { message: None }
     }
@@ -475,6 +483,57 @@ mod tests {
         assert!(matches!(submission, Submission::UserInput { content } if content == "/unknown"));
     }
 
+    #[test]
+    fn test_parser_approval_response_aliases() {
+        // approve once
+        assert!(matches!(
+            SubmissionParser::parse("y"),
+            Submission::ApprovalResponse {
+                approved: true,
+                always: false
+            }
+        ));
+        assert!(matches!(
+            SubmissionParser::parse("/approve"),
+            Submission::ApprovalResponse {
+                approved: true,
+                always: false
+            }
+        ));
+
+        // approve always
+        assert!(matches!(
+            SubmissionParser::parse("a"),
+            Submission::ApprovalResponse {
+                approved: true,
+                always: true
+            }
+        ));
+        assert!(matches!(
+            SubmissionParser::parse("/always"),
+            Submission::ApprovalResponse {
+                approved: true,
+                always: true
+            }
+        ));
+
+        // deny
+        assert!(matches!(
+            SubmissionParser::parse("n"),
+            Submission::ApprovalResponse {
+                approved: false,
+                always: false
+            }
+        ));
+        assert!(matches!(
+            SubmissionParser::parse("/deny"),
+            Submission::ApprovalResponse {
+                approved: false,
+                always: false
+            }
+        ));
+    }
+
     #[test]
     fn test_parser_json_exec_approval() {
         let req_id = Uuid::new_v4();

src/agent/task.rs

@@ -29,6 +29,7 @@ impl TaskOutput {
     }
 
     /// Create a text result.
+    #[cfg(test)]
     pub fn text(text: impl Into<String>, duration: Duration) -> Self {
         Self {
             result: serde_json::Value::String(text.into()),
@@ -37,6 +38,7 @@ impl TaskOutput {
     }
 
     /// Create an empty success result.
+    #[cfg(test)]
     pub fn empty(duration: Duration) -> Self {
         Self {
             result: serde_json::Value::Null,
@@ -130,6 +132,7 @@ impl Task {
     }
 
     /// Create a new Job task with a specific ID.
+    #[cfg(test)]
     pub fn job_with_id(id: Uuid, title: impl Into<String>, description: impl Into<String>) -> Self {
         Self::Job {
             id,
@@ -152,6 +155,7 @@ impl Task {
     }
 
     /// Create a new Background task.
+    #[cfg(test)]
     pub fn background(handler: std::sync::Arc<dyn TaskHandler>) -> Self {
         Self::Background {
             id: Uuid::new_v4(),
@@ -160,6 +164,7 @@ impl Task {
     }
 
     /// Create a new Background task with a specific ID.
+    #[cfg(test)]
     pub fn background_with_id(id: Uuid, handler: std::sync::Arc<dyn TaskHandler>) -> Self {
         Self::Background { id, handler }
     }
@@ -174,6 +179,7 @@ impl Task {
     }
 
     /// Get the parent ID for sub-tasks.
+    #[cfg(test)]
     pub fn parent_id(&self) -> Option<Uuid> {
         match self {
             Self::Job { .. } => None,
@@ -225,6 +231,7 @@ impl fmt::Debug for Task {
 }
 
 /// Status of a scheduled task.
+#[cfg(test)]
 #[derive(Debug, Clone, Copy, PartialEq, Eq)]
 pub enum TaskStatus {
     /// Task is queued waiting for execution.

src/agent/undo.rs

@@ -43,6 +43,10 @@ impl Checkpoint {
 }
 
 /// Manager for undo/redo functionality.
+///
+/// Each undo/redo operation pops from one stack and pushes the current state
+/// onto the other, so `undo_count() + redo_count()` stays constant across
+/// undo/redo cycles (only `checkpoint()` and `clear()` change the total).
 pub struct UndoManager {
     /// Stack of past checkpoints (for undo).
     undo_stack: VecDeque<Checkpoint>,
@@ -63,11 +67,20 @@ impl UndoManager {
     }
 
     /// Create with a custom checkpoint limit.
+    #[cfg(test)]
     pub fn with_max_checkpoints(mut self, max: usize) -> Self {
         self.max_checkpoints = max;
         self
     }
 
+    /// Push a checkpoint onto the undo stack, trimming oldest entries if over limit.
+    fn push_undo(&mut self, checkpoint: Checkpoint) {
+        self.undo_stack.push_back(checkpoint);
+        while self.undo_stack.len() > self.max_checkpoints {
+            self.undo_stack.pop_front();
+        }
+    }
+
     /// Create a checkpoint at the current state.
     ///
     /// This clears the redo stack since we're creating a new history branch.
@@ -80,24 +93,23 @@ impl UndoManager {
         // Clear redo stack (new branch of history)
         self.redo_stack.clear();
 
-        // Create and push checkpoint
         let checkpoint = Checkpoint::new(turn_number, messages, description);
-        self.undo_stack.push_back(checkpoint);
-
-        // Trim if over limit
-        while self.undo_stack.len() > self.max_checkpoints {
-            self.undo_stack.pop_front();
-        }
+        self.push_undo(checkpoint);
     }
 
     /// Undo: pop the last checkpoint and return it.
     ///
-    /// The current state should be saved to redo stack before calling this.
+    /// Saves the current state to the redo stack and pops the most recent
+    /// checkpoint from the undo stack so that repeated undos walk backwards
+    /// through history.
+    ///
+    /// Takes ownership of `current_messages`; callers must clone first if
+    /// they need to retain a copy.
     pub fn undo(
         &mut self,
         current_turn: usize,
         current_messages: Vec<ChatMessage>,
-    ) -> Option<&Checkpoint> {
+    ) -> Option<Checkpoint> {
         if self.undo_stack.is_empty() {
             return None;
         }
@@ -110,18 +122,40 @@ impl UndoManager {
         );
         self.redo_stack.push(current);
 
-        // Return the most recent checkpoint without removing it
-        // (we keep it so multiple undos can work)
-        self.undo_stack.back()
+        // Pop and return the most recent checkpoint
+        self.undo_stack.pop_back()
     }
 
     /// Pop the last checkpoint from the undo stack.
+    #[cfg(test)]
     pub fn pop_undo(&mut self) -> Option<Checkpoint> {
         self.undo_stack.pop_back()
     }
 
     /// Redo: restore a previously undone state.
-    pub fn redo(&mut self) -> Option<Checkpoint> {
+    ///
+    /// Saves the current state to the undo stack and pops the most recent
+    /// checkpoint from the redo stack.
+    ///
+    /// Takes ownership of `current_messages`; callers must clone first if
+    /// they need to retain a copy.
+    pub fn redo(
+        &mut self,
+        current_turn: usize,
+        current_messages: Vec<ChatMessage>,
+    ) -> Option<Checkpoint> {
+        if self.redo_stack.is_empty() {
+            return None;
+        }
+
+        // Save current state to undo stack
+        let current = Checkpoint::new(
+            current_turn,
+            current_messages,
+            format!("Turn {}", current_turn),
+        );
+        self.push_undo(current);
+
         self.redo_stack.pop()
     }
 
@@ -146,6 +180,7 @@ impl UndoManager {
     }
 
     /// Get a checkpoint by ID.
+    #[cfg(test)]
     pub fn get_checkpoint(&self, id: Uuid) -> Option<&Checkpoint> {
         self.undo_stack
             .iter()
@@ -154,6 +189,7 @@ impl UndoManager {
     }
 
     /// List all available checkpoints (for UI display).
+    #[cfg(test)]
     pub fn list_checkpoints(&self) -> Vec<&Checkpoint> {
         self.undo_stack.iter().collect()
     }
@@ -214,14 +250,16 @@ mod tests {
         assert!(manager.can_undo());
         assert!(!manager.can_redo());
 
-        // Undo
+        // Undo - returns owned Checkpoint now
         let current = vec![ChatMessage::user("Hello"), ChatMessage::assistant("Hi")];
         let checkpoint = manager.undo(2, current);
         assert!(checkpoint.is_some());
+        let checkpoint = checkpoint.unwrap();
+        assert_eq!(checkpoint.turn_number, 1);
         assert!(manager.can_redo());
 
-        // Redo
-        let restored = manager.redo();
+        // Redo - now requires current state parameters
+        let restored = manager.redo(checkpoint.turn_number, checkpoint.messages);
         assert!(restored.is_some());
     }
 
@@ -249,4 +287,90 @@ mod tests {
         assert!(restored.is_some());
         assert_eq!(manager.undo_count(), 0);
     }
+
+    #[test]
+    fn test_repeated_undo_advances_through_stack() {
+        let mut manager = UndoManager::new();
+
+        // Create 3 checkpoints at turns 0, 1, 2
+        manager.checkpoint(0, vec![], "Turn 0");
+        manager.checkpoint(1, vec![ChatMessage::user("msg1")], "Turn 1");
+        manager.checkpoint(2, vec![ChatMessage::user("msg2")], "Turn 2");
+        assert_eq!(manager.undo_count(), 3);
+
+        // First undo: should return turn 2 checkpoint, stack shrinks to 2
+        let cp1 = manager
+            .undo(3, vec![ChatMessage::user("msg3")])
+            .expect("first undo should succeed");
+        assert_eq!(cp1.turn_number, 2);
+        assert_eq!(manager.undo_count(), 2);
+
+        // Second undo: should return turn 1 checkpoint (different!), stack shrinks to 1
+        let cp2 = manager
+            .undo(cp1.turn_number, cp1.messages)
+            .expect("second undo should succeed");
+        assert_eq!(cp2.turn_number, 1);
+        assert_eq!(manager.undo_count(), 1);
+
+        // Verify we walked backwards through distinct checkpoints
+        assert_ne!(cp1.turn_number, cp2.turn_number);
+    }
+
+    #[test]
+    fn test_undo_redo_cycle_preserves_state() {
+        let mut manager = UndoManager::new();
+
+        let msgs_t0: Vec<ChatMessage> = vec![];
+        let msgs_t1 = vec![ChatMessage::user("hello")];
+        let msgs_t2 = vec![ChatMessage::user("hello"), ChatMessage::assistant("hi")];
+
+        manager.checkpoint(0, msgs_t0, "Turn 0");
+        manager.checkpoint(1, msgs_t1, "Turn 1");
+
+        // Undo from turn 2 -> get turn 1 checkpoint
+        let cp_undo1 = manager
+            .undo(2, msgs_t2.clone())
+            .expect("undo should succeed");
+        assert_eq!(cp_undo1.turn_number, 1);
+
+        // Redo from turn 1 -> get turn 2 state back
+        let cp_redo = manager
+            .redo(cp_undo1.turn_number, cp_undo1.messages)
+            .expect("redo should succeed");
+        assert_eq!(cp_redo.turn_number, 2);
+        assert_eq!(cp_redo.messages.len(), 2);
+
+        // Undo again from turn 2 -> should go back to turn 1 again
+        let cp_undo2 = manager
+            .undo(cp_redo.turn_number, cp_redo.messages)
+            .expect("second undo should succeed");
+        assert_eq!(cp_undo2.turn_number, 1);
+    }
+
+    #[test]
+    fn test_undo_redo_stack_sizes_consistent() {
+        let mut manager = UndoManager::new();
+
+        manager.checkpoint(0, vec![], "Turn 0");
+        manager.checkpoint(1, vec![ChatMessage::user("a")], "Turn 1");
+        manager.checkpoint(2, vec![ChatMessage::user("b")], "Turn 2");
+
+        // Start: undo=3, redo=0, total=3
+        let total = manager.undo_count() + manager.redo_count();
+        assert_eq!(total, 3);
+
+        // After undo: total should still be 3 (one moved from undo to redo,
+        // plus the current state pushed to redo)
+        // Actually: undo pops one (3->2), pushes current to redo (0->1), total=3
+        let cp = manager.undo(3, vec![]).unwrap();
+        assert_eq!(manager.undo_count() + manager.redo_count(), 3);
+
+        // After redo: redo pops one (1->0), pushes current to undo (2->3), total=3
+        let cp2 = manager.redo(cp.turn_number, cp.messages).unwrap();
+        assert_eq!(manager.undo_count() + manager.redo_count(), 3);
+
+        // After another undo: same invariant
+        let _cp3 = manager.undo(cp2.turn_number, cp2.messages).unwrap();
+        assert_eq!(manager.undo_count() + manager.redo_count(), 3);
+    }
 }

src/agent/worker.rs

@@ -3,8 +3,8 @@
 use std::sync::Arc;
 use std::time::Duration;
 
-use futures::future::join_all;
 use tokio::sync::mpsc;
+use tokio::task::JoinSet;
 use uuid::Uuid;
 
 use crate::agent::scheduler::WorkerMessage;
@@ -292,19 +292,21 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
                                 tool_calls.clone(),
                             ));
 
-                        for tc in tool_calls {
-                            let result = self.execute_tool(&tc.name, &tc.arguments).await;
-
-                            // Create synthetic selection for process_tool_result
-                            let selection = ToolSelection {
+                        // Convert ToolCalls to ToolSelections and execute in parallel
+                        let selections: Vec<ToolSelection> = tool_calls
+                            .iter()
+                            .map(|tc| ToolSelection {
                                 tool_name: tc.name.clone(),
                                 parameters: tc.arguments.clone(),
                                 reasoning: String::new(),
                                 alternatives: vec![],
                                 tool_call_id: tc.id.clone(),
-                            };
+                            })
+                            .collect();
 
-                            self.process_tool_result(reason_ctx, &selection, result)
+                        let results = self.execute_tools_parallel(&selections).await;
+                        for (selection, result) in selections.iter().zip(results) {
+                            self.process_tool_result(reason_ctx, selection, result.result)
                                 .await?;
                         }
                     }
@@ -347,24 +349,71 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
         }
     }
 
-    /// Execute multiple tools in parallel.
+    /// Execute multiple tools in parallel using a JoinSet.
+    ///
+    /// Each task is tagged with its original index so results are returned
+    /// in the same order as `selections`, regardless of completion order.
     async fn execute_tools_parallel(&self, selections: &[ToolSelection]) -> Vec<ToolExecResult> {
-        let futures: Vec<_> = selections
-            .iter()
-            .map(|selection| {
-                let tool_name = selection.tool_name.clone();
-                let params = selection.parameters.clone();
-                let deps = self.deps.clone();
-                let job_id = self.job_id;
+        let count = selections.len();
 
-                async move {
-                    let result = Self::execute_tool_inner(&deps, job_id, &tool_name, &params).await;
-                    ToolExecResult { result }
+        // Short-circuit for single tool: execute directly without JoinSet overhead
+        if count <= 1 {
+            let mut results = Vec::with_capacity(count);
+            for selection in selections {
+                let result = Self::execute_tool_inner(
+                    &self.deps,
+                    self.job_id,
+                    &selection.tool_name,
+                    &selection.parameters,
+                )
+                .await;
+                results.push(ToolExecResult { result });
+            }
+            return results;
+        }
+
+        let mut join_set = JoinSet::new();
+
+        for (idx, selection) in selections.iter().enumerate() {
+            let deps = self.deps.clone();
+            let job_id = self.job_id;
+            let tool_name = selection.tool_name.clone();
+            let params = selection.parameters.clone();
+            join_set.spawn(async move {
+                let result = Self::execute_tool_inner(&deps, job_id, &tool_name, &params).await;
+                (idx, ToolExecResult { result })
+            });
+        }
+
+        // Collect and reorder by original index
+        let mut results: Vec<Option<ToolExecResult>> = (0..count).map(|_| None).collect();
+        while let Some(join_result) = join_set.join_next().await {
+            match join_result {
+                Ok((idx, exec_result)) => results[idx] = Some(exec_result),
+                Err(e) => {
+                    if e.is_panic() {
+                        tracing::error!("Tool execution task panicked: {}", e);
+                    } else {
+                        tracing::error!("Tool execution task cancelled: {}", e);
+                    }
                 }
-            })
-            .collect();
+            }
+        }
 
-        join_all(futures).await
+        // Fill any panicked slots with error results
+        results
+            .into_iter()
+            .enumerate()
+            .map(|(i, opt)| {
+                opt.unwrap_or_else(|| ToolExecResult {
+                    result: Err(crate::error::ToolError::ExecutionFailed {
+                        name: selections[i].tool_name.clone(),
+                        reason: "Task failed during execution".to_string(),
+                    }
+                    .into()),
+                })
+            })
+            .collect()
     }
 
     /// Inner tool execution logic that can be called from both single and parallel paths.
@@ -505,7 +554,8 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
                 let output_str = serde_json::to_string_pretty(&output.result)
                     .ok()
                     .map(|s| deps.safety.sanitize_tool_output(tool_name, &s).content);
-                deps.context_manager
+                match deps
+                    .context_manager
                     .update_memory(job_id, |mem| {
                         let rec = mem.create_action(tool_name, params.clone()).succeed(
                             output_str.clone(),
@@ -516,30 +566,52 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
                         rec
                     })
                     .await
-                    .ok()
+                {
+                    Ok(rec) => Some(rec),
+                    Err(e) => {
+                        tracing::warn!(job_id = %job_id, tool = tool_name, "Failed to record action in memory: {e}");
+                        None
+                    }
+                }
+            }
+            Ok(Err(e)) => {
+                match deps
+                    .context_manager
+                    .update_memory(job_id, |mem| {
+                        let rec = mem
+                            .create_action(tool_name, params.clone())
+                            .fail(e.to_string(), elapsed);
+                        mem.record_action(rec.clone());
+                        rec
+                    })
+                    .await
+                {
+                    Ok(rec) => Some(rec),
+                    Err(e) => {
+                        tracing::warn!(job_id = %job_id, tool = tool_name, "Failed to record action in memory: {e}");
+                        None
+                    }
+                }
+            }
+            Err(_) => {
+                match deps
+                    .context_manager
+                    .update_memory(job_id, |mem| {
+                        let rec = mem
+                            .create_action(tool_name, params.clone())
+                            .fail("Execution timeout", elapsed);
+                        mem.record_action(rec.clone());
+                        rec
+                    })
+                    .await
+                {
+                    Ok(rec) => Some(rec),
+                    Err(e) => {
+                        tracing::warn!(job_id = %job_id, tool = tool_name, "Failed to record action in memory: {e}");
+                        None
+                    }
+                }
             }
-            Ok(Err(e)) => deps
-                .context_manager
-                .update_memory(job_id, |mem| {
-                    let rec = mem
-                        .create_action(tool_name, params.clone())
-                        .fail(e.to_string(), elapsed);
-                    mem.record_action(rec.clone());
-                    rec
-                })
-                .await
-                .ok(),
-            Err(_) => deps
-                .context_manager
-                .update_memory(job_id, |mem| {
-                    let rec = mem
-                        .create_action(tool_name, params.clone())
-                        .fail("Execution timeout", elapsed);
-                    mem.record_action(rec.clone());
-                    rec
-                })
-                .await
-                .ok(),
         };
 
         // Persist action to database (fire-and-forget)
@@ -800,6 +872,102 @@ mod tests {
     use crate::llm::ToolSelection;
     use crate::util::llm_signals_completion;
 
+    use super::*;
+    use crate::config::SafetyConfig;
+    use crate::context::JobContext;
+    use crate::llm::{
+        CompletionRequest, CompletionResponse, LlmProvider, ToolCompletionRequest,
+        ToolCompletionResponse,
+    };
+    use crate::safety::SafetyLayer;
+    use crate::tools::{Tool, ToolError, ToolOutput};
+
+    /// A test tool that sleeps for a configurable duration before returning.
+    struct SlowTool {
+        tool_name: String,
+        delay: Duration,
+    }
+
+    #[async_trait::async_trait]
+    impl Tool for SlowTool {
+        fn name(&self) -> &str {
+            &self.tool_name
+        }
+        fn description(&self) -> &str {
+            "Test tool with configurable delay"
+        }
+        fn parameters_schema(&self) -> serde_json::Value {
+            serde_json::json!({"type": "object", "properties": {}})
+        }
+        async fn execute(
+            &self,
+            _params: serde_json::Value,
+            _ctx: &JobContext,
+        ) -> Result<ToolOutput, ToolError> {
+            let start = std::time::Instant::now();
+            tokio::time::sleep(self.delay).await;
+            Ok(ToolOutput::text(
+                format!("done_{}", self.tool_name),
+                start.elapsed(),
+            ))
+        }
+        fn requires_sanitization(&self) -> bool {
+            false
+        }
+    }
+
+    /// Stub LLM provider (never called in these tests).
+    struct StubLlm;
+
+    #[async_trait::async_trait]
+    impl LlmProvider for StubLlm {
+        fn model_name(&self) -> &str {
+            "stub"
+        }
+        fn cost_per_token(&self) -> (rust_decimal::Decimal, rust_decimal::Decimal) {
+            (rust_decimal::Decimal::ZERO, rust_decimal::Decimal::ZERO)
+        }
+        async fn complete(
+            &self,
+            _req: CompletionRequest,
+        ) -> Result<CompletionResponse, crate::error::LlmError> {
+            unimplemented!("stub")
+        }
+        async fn complete_with_tools(
+            &self,
+            _req: ToolCompletionRequest,
+        ) -> Result<ToolCompletionResponse, crate::error::LlmError> {
+            unimplemented!("stub")
+        }
+    }
+
+    /// Build a Worker wired to a ToolRegistry containing the given tools.
+    async fn make_worker(tools: Vec<Arc<dyn Tool>>) -> Worker {
+        let registry = ToolRegistry::new();
+        for t in tools {
+            registry.register(t).await;
+        }
+
+        let cm = Arc::new(crate::context::ContextManager::new(5));
+        let job_id = cm.create_job("test", "test job").await.unwrap();
+
+        let deps = WorkerDeps {
+            context_manager: cm,
+            llm: Arc::new(StubLlm),
+            safety: Arc::new(SafetyLayer::new(&SafetyConfig {
+                max_output_length: 100_000,
+                injection_check_enabled: false,
+            })),
+            tools: Arc::new(registry),
+            store: None,
+            hooks: Arc::new(crate::hooks::HookRegistry::new()),
+            timeout: Duration::from_secs(30),
+            use_planning: false,
+        };
+
+        Worker::new(job_id, deps)
+    }
+
     #[test]
     fn test_tool_selection_preserves_call_id() {
         let selection = ToolSelection {
@@ -876,4 +1044,119 @@ mod tests {
             "The tool returned: TASK_COMPLETE signal"
         ));
     }
+
+    #[tokio::test]
+    async fn test_parallel_speedup() {
+        // 3 tools each sleeping 200ms should finish in roughly 200ms (parallel),
+        // not ~600ms (sequential).
+        let tools: Vec<Arc<dyn Tool>> = (0..3)
+            .map(|i| {
+                Arc::new(SlowTool {
+                    tool_name: format!("slow_{}", i),
+                    delay: Duration::from_millis(200),
+                }) as Arc<dyn Tool>
+            })
+            .collect();
+
+        let worker = make_worker(tools).await;
+
+        let selections: Vec<ToolSelection> = (0..3)
+            .map(|i| ToolSelection {
+                tool_name: format!("slow_{}", i),
+                parameters: serde_json::json!({}),
+                reasoning: String::new(),
+                alternatives: vec![],
+                tool_call_id: format!("call_{}", i),
+            })
+            .collect();
+
+        let start = std::time::Instant::now();
+        let results = worker.execute_tools_parallel(&selections).await;
+        let elapsed = start.elapsed();
+
+        assert_eq!(results.len(), 3);
+        for r in &results {
+            assert!(r.result.is_ok(), "Tool should succeed");
+        }
+        // Parallel should complete well under the sequential 600ms threshold.
+        assert!(
+            elapsed < Duration::from_millis(500),
+            "Parallel execution took {:?}, expected < 500ms",
+            elapsed
+        );
+    }
+
+    #[tokio::test]
+    async fn test_result_ordering_preserved() {
+        // Tools with different delays finish in different order.
+        // Results must be returned in the original request order.
+        let tools: Vec<Arc<dyn Tool>> = vec![
+            Arc::new(SlowTool {
+                tool_name: "tool_a".into(),
+                delay: Duration::from_millis(300),
+            }),
+            Arc::new(SlowTool {
+                tool_name: "tool_b".into(),
+                delay: Duration::from_millis(100),
+            }),
+            Arc::new(SlowTool {
+                tool_name: "tool_c".into(),
+                delay: Duration::from_millis(200),
+            }),
+        ];
+
+        let worker = make_worker(tools).await;
+
+        let selections = vec![
+            ToolSelection {
+                tool_name: "tool_a".into(),
+                parameters: serde_json::json!({}),
+                reasoning: String::new(),
+                alternatives: vec![],
+                tool_call_id: "call_a".into(),
+            },
+            ToolSelection {
+                tool_name: "tool_b".into(),
+                parameters: serde_json::json!({}),
+                reasoning: String::new(),
+                alternatives: vec![],
+                tool_call_id: "call_b".into(),
+            },
+            ToolSelection {
+                tool_name: "tool_c".into(),
+                parameters: serde_json::json!({}),
+                reasoning: String::new(),
+                alternatives: vec![],
+                tool_call_id: "call_c".into(),
+            },
+        ];
+
+        let results = worker.execute_tools_parallel(&selections).await;
+
+        // Results must be in same order as selections, not completion order.
+        assert!(results[0].result.as_ref().unwrap().contains("done_tool_a"));
+        assert!(results[1].result.as_ref().unwrap().contains("done_tool_b"));
+        assert!(results[2].result.as_ref().unwrap().contains("done_tool_c"));
+    }
+
+    #[tokio::test]
+    async fn test_missing_tool_produces_error_not_panic() {
+        // If a tool doesn't exist, the result slot should contain an error.
+        let worker = make_worker(vec![]).await;
+
+        let selections = vec![ToolSelection {
+            tool_name: "nonexistent_tool".into(),
+            parameters: serde_json::json!({}),
+            reasoning: String::new(),
+            alternatives: vec![],
+            tool_call_id: "call_x".into(),
+        }];
+
+        let results = worker.execute_tools_parallel(&selections).await;
+        assert_eq!(results.len(), 1);
+        assert!(
+            results[0].result.is_err(),
+            "Missing tool should produce an error, not a panic"
+        );
+    }
 }

src/app.rs

@@ -0,0 +1,780 @@
+//! Application builder for initializing core IronClaw components.
+//!
+//! Extracts the mechanical initialization phases from `main.rs` into a
+//! reusable builder so that:
+//!
+//! - Tests can construct a full `AppComponents` without wiring channels
+//! - Main stays focused on CLI dispatch and channel setup
+//! - Each init phase is independently testable
+
+use std::sync::Arc;
+
+use crate::channels::web::log_layer::LogBroadcaster;
+use crate::config::Config;
+use crate::context::ContextManager;
+use crate::db::Database;
+use crate::extensions::ExtensionManager;
+use crate::hooks::HookRegistry;
+use crate::llm::{LlmProvider, SessionManager};
+use crate::safety::SafetyLayer;
+use crate::secrets::SecretsStore;
+use crate::skills::SkillRegistry;
+use crate::skills::catalog::SkillCatalog;
+use crate::tools::ToolRegistry;
+use crate::tools::mcp::McpSessionManager;
+use crate::tools::wasm::WasmToolRuntime;
+use crate::workspace::{EmbeddingProvider, Workspace};
+
+/// Fully initialized application components, ready for channel wiring
+/// and agent construction.
+pub struct AppComponents {
+    /// The (potentially mutated) config after DB reload and secret injection.
+    pub config: Config,
+    pub db: Option<Arc<dyn Database>>,
+    pub secrets_store: Option<Arc<dyn SecretsStore + Send + Sync>>,
+    pub llm: Arc<dyn LlmProvider>,
+    pub cheap_llm: Option<Arc<dyn LlmProvider>>,
+    pub safety: Arc<SafetyLayer>,
+    pub tools: Arc<ToolRegistry>,
+    pub embeddings: Option<Arc<dyn EmbeddingProvider>>,
+    pub workspace: Option<Arc<Workspace>>,
+    pub extension_manager: Option<Arc<ExtensionManager>>,
+    pub mcp_session_manager: Arc<McpSessionManager>,
+    pub wasm_tool_runtime: Option<Arc<WasmToolRuntime>>,
+    pub log_broadcaster: Arc<LogBroadcaster>,
+    pub context_manager: Arc<ContextManager>,
+    pub hooks: Arc<HookRegistry>,
+    pub skill_registry: Option<Arc<std::sync::RwLock<SkillRegistry>>>,
+    pub skill_catalog: Option<Arc<SkillCatalog>>,
+    pub cost_guard: Arc<crate::agent::cost_guard::CostGuard>,
+    pub session: Arc<SessionManager>,
+}
+
+/// Options that control optional init phases.
+#[derive(Default)]
+pub struct AppBuilderFlags {
+    pub no_db: bool,
+}
+
+/// Builder that orchestrates the 5 mechanical init phases.
+pub struct AppBuilder {
+    config: Config,
+    flags: AppBuilderFlags,
+    toml_path: Option<std::path::PathBuf>,
+    session: Arc<SessionManager>,
+    log_broadcaster: Arc<LogBroadcaster>,
+
+    // Accumulated state
+    db: Option<Arc<dyn Database>>,
+    secrets_store: Option<Arc<dyn SecretsStore + Send + Sync>>,
+
+    // Backend-specific handles needed by secrets store
+    #[cfg(feature = "postgres")]
+    pg_pool: Option<deadpool_postgres::Pool>,
+    #[cfg(feature = "libsql")]
+    libsql_db: Option<Arc<libsql::Database>>,
+}
+
+impl AppBuilder {
+    /// Create a new builder.
+    ///
+    /// The `session` and `log_broadcaster` are created before the builder
+    /// because tracing must be initialized before any init phase runs,
+    /// and the log broadcaster is part of the tracing layer.
+    pub fn new(
+        config: Config,
+        flags: AppBuilderFlags,
+        toml_path: Option<std::path::PathBuf>,
+        session: Arc<SessionManager>,
+        log_broadcaster: Arc<LogBroadcaster>,
+    ) -> Self {
+        Self {
+            config,
+            flags,
+            toml_path,
+            session,
+            log_broadcaster,
+            db: None,
+            secrets_store: None,
+            #[cfg(feature = "postgres")]
+            pg_pool: None,
+            #[cfg(feature = "libsql")]
+            libsql_db: None,
+        }
+    }
+
+    /// Phase 1: Initialize database backend.
+    ///
+    /// Creates the database connection, runs migrations, reloads config
+    /// from DB, attaches DB to session manager, and cleans up stale jobs.
+    pub async fn init_database(&mut self) -> Result<(), anyhow::Error> {
+        if self.flags.no_db {
+            tracing::warn!("Running without database connection");
+            return Ok(());
+        }
+
+        let db: Arc<dyn Database> = match self.config.database.backend {
+            #[cfg(feature = "libsql")]
+            crate::config::DatabaseBackend::LibSql => {
+                use crate::db::Database as _;
+                use crate::db::libsql::LibSqlBackend;
+                use secrecy::ExposeSecret as _;
+
+                let default_path = crate::config::default_libsql_path();
+                let db_path = self
+                    .config
+                    .database
+                    .libsql_path
+                    .as_deref()
+                    .unwrap_or(&default_path);
+
+                let backend = if let Some(ref url) = self.config.database.libsql_url {
+                    let token =
+                        self.config
+                            .database
+                            .libsql_auth_token
+                            .as_ref()
+                            .ok_or_else(|| {
+                                anyhow::anyhow!(
+                                    "LIBSQL_AUTH_TOKEN is required when LIBSQL_URL is set"
+                                )
+                            })?;
+                    LibSqlBackend::new_remote_replica(db_path, url, token.expose_secret()).await?
+                } else {
+                    LibSqlBackend::new_local(db_path).await?
+                };
+                backend.run_migrations().await?;
+                tracing::info!("libSQL database connected and migrations applied");
+
+                #[cfg(feature = "libsql")]
+                {
+                    self.libsql_db = Some(backend.shared_db());
+                }
+
+                Arc::new(backend) as Arc<dyn Database>
+            }
+            #[cfg(feature = "postgres")]
+            _ => {
+                use crate::db::Database as _;
+                let pg = crate::db::postgres::PgBackend::new(&self.config.database)
+                    .await
+                    .map_err(|e| anyhow::anyhow!("{}", e))?;
+                pg.run_migrations()
+                    .await
+                    .map_err(|e| anyhow::anyhow!("{}", e))?;
+                tracing::info!("PostgreSQL database connected and migrations applied");
+
+                #[cfg(feature = "postgres")]
+                {
+                    self.pg_pool = Some(pg.pool());
+                }
+
+                Arc::new(pg) as Arc<dyn Database>
+            }
+            #[cfg(not(feature = "postgres"))]
+            _ => {
+                anyhow::bail!(
+                    "No database backend available. Enable 'postgres' or 'libsql' feature."
+                );
+            }
+        };
+
+        // Post-init: migrate disk config, reload config from DB, attach session, cleanup
+        if let Err(e) = crate::bootstrap::migrate_disk_to_db(db.as_ref(), "default").await {
+            tracing::warn!("Disk-to-DB settings migration failed: {}", e);
+        }
+
+        let toml_path = self.toml_path.as_deref();
+        match Config::from_db_with_toml(db.as_ref(), "default", toml_path).await {
+            Ok(db_config) => {
+                self.config = db_config;
+                tracing::info!("Configuration reloaded from database");
+            }
+            Err(e) => {
+                tracing::warn!(
+                    "Failed to reload config from DB, keeping env-based config: {}",
+                    e
+                );
+            }
+        }
+
+        self.session.attach_store(db.clone(), "default").await;
+
+        if let Err(e) = db.cleanup_stale_sandbox_jobs().await {
+            tracing::warn!("Failed to cleanup stale sandbox jobs: {}", e);
+        }
+
+        self.db = Some(db);
+        Ok(())
+    }
+
+    /// Phase 2: Create secrets store.
+    ///
+    /// Requires a master key and a backend-specific DB handle. After creating
+    /// the store, injects any encrypted LLM API keys into the config overlay
+    /// and re-resolves config.
+    pub async fn init_secrets(&mut self) -> Result<(), anyhow::Error> {
+        let master_key = match self.config.secrets.master_key() {
+            Some(k) => k,
+            None => {
+                // Consume unused handles
+                #[cfg(feature = "libsql")]
+                {
+                    self.libsql_db.take();
+                }
+                return Ok(());
+            }
+        };
+
+        let crypto = match crate::secrets::SecretsCrypto::new(master_key.clone()) {
+            Ok(c) => Arc::new(c),
+            Err(e) => {
+                tracing::warn!("Failed to initialize secrets crypto: {}", e);
+                #[cfg(feature = "libsql")]
+                {
+                    self.libsql_db.take();
+                }
+                return Ok(());
+            }
+        };
+
+        let store: Option<Arc<dyn SecretsStore + Send + Sync>> = None;
+
+        #[cfg(feature = "libsql")]
+        let store = store.or_else(|| {
+            self.libsql_db.take().map(|db| {
+                Arc::new(crate::secrets::LibSqlSecretsStore::new(
+                    db,
+                    Arc::clone(&crypto),
+                )) as Arc<dyn SecretsStore + Send + Sync>
+            })
+        });
+
+        #[cfg(feature = "postgres")]
+        let store = store.or_else(|| {
+            self.pg_pool.as_ref().map(|pool| {
+                Arc::new(crate::secrets::PostgresSecretsStore::new(
+                    pool.clone(),
+                    Arc::clone(&crypto),
+                )) as Arc<dyn SecretsStore + Send + Sync>
+            })
+        });
+
+        if let Some(ref secrets) = store {
+            // Inject LLM API keys from encrypted storage
+            crate::config::inject_llm_keys_from_secrets(secrets.as_ref(), "default").await;
+
+            // Re-resolve config with newly available keys
+            if let Some(ref db) = self.db {
+                let toml_path = self.toml_path.as_deref();
+                match Config::from_db_with_toml(db.as_ref(), "default", toml_path).await {
+                    Ok(refreshed) => {
+                        self.config = refreshed;
+                        tracing::debug!("LlmConfig re-resolved after secret injection");
+                    }
+                    Err(e) => {
+                        tracing::warn!("Failed to re-resolve config after secret injection: {}", e);
+                    }
+                }
+            }
+        }
+
+        self.secrets_store = store;
+        Ok(())
+    }
+
+    /// Phase 3: Initialize LLM provider chain.
+    ///
+    /// Creates the primary provider, then wraps with failover, circuit
+    /// breaker, and response cache as configured.
+    #[allow(clippy::type_complexity)]
+    pub fn init_llm(
+        &self,
+    ) -> Result<(Arc<dyn LlmProvider>, Option<Arc<dyn LlmProvider>>), anyhow::Error> {
+        use crate::llm::{
+            CachedProvider, CircuitBreakerConfig, CircuitBreakerProvider, CooldownConfig,
+            FailoverProvider, ResponseCacheConfig, create_cheap_llm_provider, create_llm_provider,
+            create_llm_provider_with_config,
+        };
+
+        let llm = create_llm_provider(&self.config.llm, self.session.clone())?;
+        tracing::info!("LLM provider initialized: {}", llm.model_name());
+
+        // Wrap in failover if a fallback model is configured
+        let llm: Arc<dyn LlmProvider> = if let Some(fallback_model) =
+            self.config.llm.nearai.fallback_model.as_ref()
+        {
+            if fallback_model == &self.config.llm.nearai.model {
+                tracing::warn!(
+                    "fallback_model is the same as primary model, failover may not be effective"
+                );
+            }
+            let mut fallback_config = self.config.llm.nearai.clone();
+            fallback_config.model = fallback_model.clone();
+            let fallback = create_llm_provider_with_config(&fallback_config, self.session.clone())?;
+            tracing::info!(
+                primary = %llm.model_name(),
+                fallback = %fallback.model_name(),
+                "LLM failover enabled"
+            );
+            let cooldown_config = CooldownConfig {
+                cooldown_duration: std::time::Duration::from_secs(
+                    self.config.llm.nearai.failover_cooldown_secs,
+                ),
+                failure_threshold: self.config.llm.nearai.failover_cooldown_threshold,
+            };
+            Arc::new(FailoverProvider::with_cooldown(
+                vec![llm, fallback],
+                cooldown_config,
+            )?)
+        } else {
+            llm
+        };
+
+        // Wrap in circuit breaker if configured
+        let llm: Arc<dyn LlmProvider> =
+            if let Some(threshold) = self.config.llm.nearai.circuit_breaker_threshold {
+                let cb_config = CircuitBreakerConfig {
+                    failure_threshold: threshold,
+                    recovery_timeout: std::time::Duration::from_secs(
+                        self.config.llm.nearai.circuit_breaker_recovery_secs,
+                    ),
+                    ..CircuitBreakerConfig::default()
+                };
+                tracing::info!(
+                    threshold,
+                    recovery_secs = self.config.llm.nearai.circuit_breaker_recovery_secs,
+                    "LLM circuit breaker enabled"
+                );
+                Arc::new(CircuitBreakerProvider::new(llm, cb_config))
+            } else {
+                llm
+            };
+
+        // Wrap in response cache if configured
+        let llm: Arc<dyn LlmProvider> = if self.config.llm.nearai.response_cache_enabled {
+            let rc_config = ResponseCacheConfig {
+                ttl: std::time::Duration::from_secs(self.config.llm.nearai.response_cache_ttl_secs),
+                max_entries: self.config.llm.nearai.response_cache_max_entries,
+            };
+            tracing::info!(
+                ttl_secs = self.config.llm.nearai.response_cache_ttl_secs,
+                max_entries = self.config.llm.nearai.response_cache_max_entries,
+                "LLM response cache enabled"
+            );
+            Arc::new(CachedProvider::new(llm, rc_config))
+        } else {
+            llm
+        };
+
+        // Cheap LLM for lightweight tasks
+        let cheap_llm = create_cheap_llm_provider(&self.config.llm, self.session.clone())?;
+        if let Some(ref cheap) = cheap_llm {
+            tracing::info!("Cheap LLM provider initialized: {}", cheap.model_name());
+        }
+
+        Ok((llm, cheap_llm))
+    }
+
+    /// Phase 4: Initialize safety, tools, embeddings, and workspace.
+    pub async fn init_tools(
+        &self,
+        llm: &Arc<dyn LlmProvider>,
+    ) -> Result<
+        (
+            Arc<SafetyLayer>,
+            Arc<ToolRegistry>,
+            Option<Arc<dyn EmbeddingProvider>>,
+            Option<Arc<Workspace>>,
+        ),
+        anyhow::Error,
+    > {
+        use crate::workspace::{NearAiEmbeddings, OpenAiEmbeddings};
+
+        let safety = Arc::new(SafetyLayer::new(&self.config.safety));
+        tracing::info!("Safety layer initialized");
+
+        let tools = Arc::new(ToolRegistry::new());
+        tools.register_builtin_tools();
+
+        // Create embeddings provider if configured
+        let embeddings: Option<Arc<dyn EmbeddingProvider>> = if self.config.embeddings.enabled {
+            match self.config.embeddings.provider.as_str() {
+                "nearai" => {
+                    tracing::info!(
+                        "Embeddings enabled via NEAR AI (model: {})",
+                        self.config.embeddings.model
+                    );
+                    Some(Arc::new(
+                        NearAiEmbeddings::new(
+                            &self.config.llm.nearai.base_url,
+                            self.session.clone(),
+                        )
+                        .with_model(&self.config.embeddings.model, 1536),
+                    ))
+                }
+                _ => {
+                    if let Some(api_key) = self.config.embeddings.openai_api_key() {
+                        tracing::info!(
+                            "Embeddings enabled via OpenAI (model: {})",
+                            self.config.embeddings.model
+                        );
+                        Some(Arc::new(OpenAiEmbeddings::with_model(
+                            api_key,
+                            &self.config.embeddings.model,
+                            match self.config.embeddings.model.as_str() {
+                                "text-embedding-3-large" => 3072,
+                                _ => 1536,
+                            },
+                        )))
+                    } else {
+                        tracing::warn!("Embeddings configured but OPENAI_API_KEY not set");
+                        None
+                    }
+                }
+            }
+        } else {
+            tracing::info!("Embeddings disabled (set OPENAI_API_KEY or EMBEDDING_ENABLED=true)");
+            None
+        };
+
+        // Register memory tools if database is available
+        let workspace = if let Some(ref db) = self.db {
+            let mut ws = Workspace::new_with_db("default", db.clone());
+            if let Some(ref emb) = embeddings {
+                ws = ws.with_embeddings(emb.clone());
+            }
+            let ws = Arc::new(ws);
+            tools.register_memory_tools(Arc::clone(&ws));
+            Some(ws)
+        } else {
+            None
+        };
+
+        // Register builder tool if enabled
+        if self.config.builder.enabled
+            && (self.config.agent.allow_local_tools || !self.config.sandbox.enabled)
+        {
+            tools
+                .register_builder_tool(
+                    llm.clone(),
+                    safety.clone(),
+                    Some(self.config.builder.to_builder_config()),
+                )
+                .await;
+            tracing::info!("Builder mode enabled");
+        }
+
+        Ok((safety, tools, embeddings, workspace))
+    }
+
+    /// Phase 5: Load WASM tools, MCP servers, and create extension manager.
+    pub async fn init_extensions(
+        &self,
+        tools: &Arc<ToolRegistry>,
+        hooks: &Arc<HookRegistry>,
+    ) -> Result<
+        (
+            Arc<McpSessionManager>,
+            Option<Arc<WasmToolRuntime>>,
+            Option<Arc<ExtensionManager>>,
+        ),
+        anyhow::Error,
+    > {
+        use crate::tools::mcp::{McpClient, config::load_mcp_servers_from_db, is_authenticated};
+        use crate::tools::wasm::{WasmToolLoader, load_dev_tools};
+
+        let mcp_session_manager = Arc::new(McpSessionManager::new());
+
+        // Create WASM tool runtime
+        let wasm_tool_runtime: Option<Arc<WasmToolRuntime>> =
+            if self.config.wasm.enabled && self.config.wasm.tools_dir.exists() {
+                match WasmToolRuntime::new(self.config.wasm.to_runtime_config()) {
+                    Ok(runtime) => Some(Arc::new(runtime)),
+                    Err(e) => {
+                        tracing::warn!("Failed to initialize WASM runtime: {}", e);
+                        None
+                    }
+                }
+            } else {
+                None
+            };
+
+        // Load WASM tools and MCP servers concurrently
+        let wasm_tools_future = {
+            let wasm_tool_runtime = wasm_tool_runtime.clone();
+            let secrets_store = self.secrets_store.clone();
+            let tools = Arc::clone(tools);
+            let wasm_config = self.config.wasm.clone();
+            async move {
+                if let Some(ref runtime) = wasm_tool_runtime {
+                    let mut loader = WasmToolLoader::new(Arc::clone(runtime), Arc::clone(&tools));
+                    if let Some(ref secrets) = secrets_store {
+                        loader = loader.with_secrets_store(Arc::clone(secrets));
+                    }
+
+                    match loader.load_from_dir(&wasm_config.tools_dir).await {
+                        Ok(results) => {
+                            if !results.loaded.is_empty() {
+                                tracing::info!(
+                                    "Loaded {} WASM tools from {}",
+                                    results.loaded.len(),
+                                    wasm_config.tools_dir.display()
+                                );
+                            }
+                            for (path, err) in &results.errors {
+                                tracing::warn!(
+                                    "Failed to load WASM tool {}: {}",
+                                    path.display(),
+                                    err
+                                );
+                            }
+                        }
+                        Err(e) => {
+                            tracing::warn!("Failed to scan WASM tools directory: {}", e);
+                        }
+                    }
+
+                    match load_dev_tools(&loader, &wasm_config.tools_dir).await {
+                        Ok(results) => {
+                            if !results.loaded.is_empty() {
+                                tracing::info!(
+                                    "Loaded {} dev WASM tools from build artifacts",
+                                    results.loaded.len()
+                                );
+                            }
+                        }
+                        Err(e) => {
+                            tracing::debug!("No dev WASM tools found: {}", e);
+                        }
+                    }
+                }
+            }
+        };
+
+        let mcp_servers_future = {
+            let secrets_store = self.secrets_store.clone();
+            let db = self.db.clone();
+            let tools = Arc::clone(tools);
+            let mcp_sm = Arc::clone(&mcp_session_manager);
+            async move {
+                if let Some(ref secrets) = secrets_store {
+                    let servers_result = if let Some(ref d) = db {
+                        load_mcp_servers_from_db(d.as_ref(), "default").await
+                    } else {
+                        crate::tools::mcp::config::load_mcp_servers().await
+                    };
+                    match servers_result {
+                        Ok(servers) => {
+                            let enabled: Vec<_> = servers.enabled_servers().cloned().collect();
+                            if !enabled.is_empty() {
+                                tracing::info!(
+                                    "Loading {} configured MCP server(s)...",
+                                    enabled.len()
+                                );
+                            }
+
+                            let mut join_set = tokio::task::JoinSet::new();
+                            for server in enabled {
+                                let mcp_sm = Arc::clone(&mcp_sm);
+                                let secrets = Arc::clone(secrets);
+                                let tools = Arc::clone(&tools);
+
+                                join_set.spawn(async move {
+                                    let server_name = server.name.clone();
+                                    let has_tokens =
+                                        is_authenticated(&server, &secrets, "default").await;
+
+                                    let client = if has_tokens || server.requires_auth() {
+                                        McpClient::new_authenticated(
+                                            server, mcp_sm, secrets, "default",
+                                        )
+                                    } else {
+                                        McpClient::new_with_name(&server_name, &server.url)
+                                    };
+
+                                    match client.list_tools().await {
+                                        Ok(mcp_tools) => {
+                                            let tool_count = mcp_tools.len();
+                                            match client.create_tools().await {
+                                                Ok(tool_impls) => {
+                                                    for tool in tool_impls {
+                                                        tools.register(tool).await;
+                                                    }
+                                                    tracing::info!(
+                                                        "Loaded {} tools from MCP server '{}'",
+                                                        tool_count,
+                                                        server_name
+                                                    );
+                                                }
+                                                Err(e) => {
+                                                    tracing::warn!(
+                                                        "Failed to create tools from MCP server '{}': {}",
+                                                        server_name,
+                                                        e
+                                                    );
+                                                }
+                                            }
+                                        }
+                                        Err(e) => {
+                                            let err_str = e.to_string();
+                                            if err_str.contains("401")
+                                                || err_str.contains("authentication")
+                                            {
+                                                tracing::warn!(
+                                                    "MCP server '{}' requires authentication. \
+                                                     Run: ironclaw mcp auth {}",
+                                                    server_name,
+                                                    server_name
+                                                );
+                                            } else {
+                                                tracing::warn!(
+                                                    "Failed to connect to MCP server '{}': {}",
+                                                    server_name,
+                                                    e
+                                                );
+                                            }
+                                        }
+                                    }
+                                });
+                            }
+
+                            while let Some(result) = join_set.join_next().await {
+                                if let Err(e) = result {
+                                    tracing::warn!("MCP server loading task panicked: {}", e);
+                                }
+                            }
+                        }
+                        Err(e) => {
+                            tracing::debug!("No MCP servers configured ({})", e);
+                        }
+                    }
+                }
+            }
+        };
+
+        tokio::join!(wasm_tools_future, mcp_servers_future);
+
+        // Create extension manager
+        let extension_manager = if let Some(ref secrets) = self.secrets_store {
+            let manager = Arc::new(ExtensionManager::new(
+                Arc::clone(&mcp_session_manager),
+                Arc::clone(secrets),
+                Arc::clone(tools),
+                Some(Arc::clone(hooks)),
+                wasm_tool_runtime.clone(),
+                self.config.wasm.tools_dir.clone(),
+                self.config.channels.wasm_channels_dir.clone(),
+                self.config.tunnel.public_url.clone(),
+                "default".to_string(),
+                self.db.clone(),
+            ));
+            tools.register_extension_tools(Arc::clone(&manager));
+            tracing::info!("Extension manager initialized with in-chat discovery tools");
+            Some(manager)
+        } else {
+            tracing::debug!(
+                "Extension manager not available (no secrets store). \
+                 Extension tools won't be registered."
+            );
+            None
+        };
+
+        // register_builder_tool() already calls register_dev_tools() internally,
+        // so only register them here when the builder didn't already do it.
+        let builder_registered_dev_tools = self.config.builder.enabled
+            && (self.config.agent.allow_local_tools || !self.config.sandbox.enabled);
+        if self.config.agent.allow_local_tools && !builder_registered_dev_tools {
+            tools.register_dev_tools();
+        }
+
+        Ok((mcp_session_manager, wasm_tool_runtime, extension_manager))
+    }
+
+    /// Run all init phases in order and return the assembled components.
+    pub async fn build_all(mut self) -> Result<AppComponents, anyhow::Error> {
+        self.init_database().await?;
+        self.init_secrets().await?;
+
+        let (llm, cheap_llm) = self.init_llm()?;
+        let (safety, tools, embeddings, workspace) = self.init_tools(&llm).await?;
+
+        // Create hook registry early so runtime extension activation can register hooks.
+        let hooks = Arc::new(HookRegistry::new());
+
+        let (mcp_session_manager, wasm_tool_runtime, extension_manager) =
+            self.init_extensions(&tools, &hooks).await?;
+
+        // Seed workspace and backfill embeddings
+        if let Some(ref ws) = workspace {
+            match ws.seed_if_empty().await {
+                Ok(_) => {}
+                Err(e) => {
+                    tracing::warn!("Failed to seed workspace: {}", e);
+                }
+            }
+
+            if embeddings.is_some() {
+                match ws.backfill_embeddings().await {
+                    Ok(count) if count > 0 => {
+                        tracing::info!("Backfilled embeddings for {} chunks", count);
+                    }
+                    Ok(_) => {}
+                    Err(e) => {
+                        tracing::warn!("Failed to backfill embeddings: {}", e);
+                    }
+                }
+            }
+        }
+
+        // Skills system
+        let (skill_registry, skill_catalog) = if self.config.skills.enabled {
+            let mut registry = SkillRegistry::new(self.config.skills.local_dir.clone());
+            let loaded = registry.discover_all().await;
+            if !loaded.is_empty() {
+                tracing::info!("Loaded {} skill(s): {}", loaded.len(), loaded.join(", "));
+            }
+            let registry = Arc::new(std::sync::RwLock::new(registry));
+            let catalog = crate::skills::catalog::shared_catalog();
+            tools.register_skill_tools(Arc::clone(&registry), Arc::clone(&catalog));
+            (Some(registry), Some(catalog))
+        } else {
+            (None, None)
+        };
+
+        let context_manager = Arc::new(ContextManager::new(self.config.agent.max_parallel_jobs));
+        let cost_guard = Arc::new(crate::agent::cost_guard::CostGuard::new(
+            crate::agent::cost_guard::CostGuardConfig {
+                max_cost_per_day_cents: self.config.agent.max_cost_per_day_cents,
+                max_actions_per_hour: self.config.agent.max_actions_per_hour,
+            },
+        ));
+
+        tracing::info!(
+            "Tool registry initialized with {} total tools",
+            tools.count()
+        );
+
+        Ok(AppComponents {
+            config: self.config,
+            db: self.db,
+            secrets_store: self.secrets_store,
+            llm,
+            cheap_llm,
+            safety,
+            tools,
+            embeddings,
+            workspace,
+            extension_manager,
+            mcp_session_manager,
+            wasm_tool_runtime,
+            log_broadcaster: self.log_broadcaster,
+            context_manager,
+            hooks,
+            skill_registry,
+            skill_catalog,
+            cost_guard,
+            session: self.session,
+        })
+    }
+}

src/boot_screen.rs

@@ -23,6 +23,10 @@ pub struct BootInfo {
     pub claude_code_enabled: bool,
     pub routines_enabled: bool,
     pub channels: Vec<String>,
+    /// Public URL from a managed tunnel (e.g., "https://abc.ngrok.io").
+    pub tunnel_url: Option<String>,
+    /// Provider name for the managed tunnel (e.g., "ngrok").
+    pub tunnel_provider: Option<String>,
 }
 
 /// Print the boot screen to stdout.
@@ -116,6 +120,16 @@ pub fn print_boot_screen(info: &BootInfo) {
         println!("  {dim}gateway{reset}   {yellow_underline}{url}{reset}");
     }
 
+    // Tunnel URL
+    if let Some(ref url) = info.tunnel_url {
+        let provider_tag = info
+            .tunnel_provider
+            .as_deref()
+            .map(|p| format!(" {dim}({p}){reset}"))
+            .unwrap_or_default();
+        println!("  {dim}tunnel{reset}    {yellow_underline}{url}{reset}{provider_tag}");
+    }
+
     println!();
     println!("{border}");
     println!();
@@ -151,6 +165,8 @@ mod tests {
                 "gateway".to_string(),
                 "telegram".to_string(),
             ],
+            tunnel_url: Some("https://abc123.ngrok.io".to_string()),
+            tunnel_provider: Some("ngrok".to_string()),
         };
         // Should not panic
         print_boot_screen(&info);
@@ -176,6 +192,8 @@ mod tests {
             claude_code_enabled: false,
             routines_enabled: false,
             channels: vec![],
+            tunnel_url: None,
+            tunnel_provider: None,
         };
         // Should not panic
         print_boot_screen(&info);
@@ -201,6 +219,8 @@ mod tests {
             claude_code_enabled: false,
             routines_enabled: false,
             channels: vec!["repl".to_string()],
+            tunnel_url: None,
+            tunnel_provider: None,
         };
         // Should not panic
         print_boot_screen(&info);

src/bootstrap.rs

@@ -98,9 +98,72 @@ pub fn save_bootstrap_env(vars: &[(&str, &str)]) -> std::io::Result<()> {
     }
     let mut content = String::new();
     for (key, value) in vars {
-        content.push_str(&format!("{}=\"{}\"\n", key, value));
+        // Escape backslashes and double quotes to prevent env var injection
+        // (e.g. a value containing `"\nINJECTED="x` would break out of quotes).
+        let escaped = value.replace('\\', "\\\\").replace('"', "\\\"");
+        content.push_str(&format!("{}=\"{}\"\n", key, escaped));
     }
-    std::fs::write(&path, content)
+    std::fs::write(&path, &content)?;
+    restrict_file_permissions(&path)?;
+    Ok(())
+}
+
+/// Update or add a single variable in `~/.ironclaw/.env`, preserving existing content.
+///
+/// Unlike `save_bootstrap_env` (which overwrites the entire file), this
+/// reads the current `.env`, replaces the line for `key` if it exists,
+/// or appends it otherwise. Use this when writing a single bootstrap var
+/// outside the wizard (which manages the full set via `save_bootstrap_env`).
+pub fn upsert_bootstrap_var(key: &str, value: &str) -> std::io::Result<()> {
+    let path = ironclaw_env_path();
+    if let Some(parent) = path.parent() {
+        std::fs::create_dir_all(parent)?;
+    }
+
+    let escaped = value.replace('\\', "\\\\").replace('"', "\\\"");
+    let new_line = format!("{}=\"{}\"", key, escaped);
+    let prefix = format!("{}=", key);
+
+    let existing = std::fs::read_to_string(&path).unwrap_or_default();
+
+    let mut found = false;
+    let mut result = String::new();
+    for line in existing.lines() {
+        if line.starts_with(&prefix) {
+            if !found {
+                result.push_str(&new_line);
+                result.push('\n');
+                found = true;
+            }
+            // Skip duplicate lines for this key
+            continue;
+        }
+        result.push_str(line);
+        result.push('\n');
+    }
+
+    if !found {
+        result.push_str(&new_line);
+        result.push('\n');
+    }
+
+    std::fs::write(&path, result)?;
+    restrict_file_permissions(&path)?;
+    Ok(())
+}
+
+/// Set restrictive file permissions (0o600) on Unix systems.
+///
+/// The `.env` file may contain database credentials and API keys,
+/// so it should only be readable by the owner.
+fn restrict_file_permissions(_path: &std::path::Path) -> std::io::Result<()> {
+    #[cfg(unix)]
+    {
+        use std::os::unix::fs::PermissionsExt;
+        let perms = std::fs::Permissions::from_mode(0o600);
+        std::fs::set_permissions(_path, perms)?;
+    }
+    Ok(())
 }
 
 /// Write `DATABASE_URL` to `~/.ironclaw/.env`.
@@ -323,6 +386,34 @@ mod tests {
         assert!(content.contains("DATABASE_URL=postgres://test"));
     }
 
+    #[test]
+    fn test_save_bootstrap_env_escapes_quotes() {
+        let dir = tempdir().unwrap();
+        let env_path = dir.path().join(".env");
+
+        // A malicious URL attempting to inject a second env var
+        let malicious = r#"http://evil.com"
+INJECTED="pwned"#;
+        let mut content = String::new();
+        let escaped = malicious.replace('\\', "\\\\").replace('"', "\\\"");
+        content.push_str(&format!("LLM_BASE_URL=\"{}\"\n", escaped));
+        std::fs::write(&env_path, &content).unwrap();
+
+        let parsed: Vec<(String, String)> = dotenvy::from_path_iter(&env_path)
+            .unwrap()
+            .filter_map(|r| r.ok())
+            .collect();
+
+        // Must parse as exactly one variable, not two
+        assert_eq!(parsed.len(), 1, "injection must not create extra vars");
+        assert_eq!(parsed[0].0, "LLM_BASE_URL");
+        // The value should contain the original malicious content (unescaped by dotenvy)
+        assert!(
+            parsed[0].1.contains("INJECTED"),
+            "value should contain the literal injection attempt, not execute it"
+        );
+    }
+
     #[test]
     fn test_ironclaw_env_path() {
         let path = ironclaw_env_path();
@@ -461,4 +552,32 @@ mod tests {
         assert_eq!(parsed.len(), 2);
         assert!(parsed.iter().all(|(k, _)| k != "DATABASE_URL"));
     }
+
+    #[test]
+    fn test_onboard_completed_round_trips_through_env() {
+        let dir = tempdir().unwrap();
+        let env_path = dir.path().join(".env");
+
+        // Simulate what the wizard writes: bootstrap vars + ONBOARD_COMPLETED
+        let vars = [
+            ("DATABASE_BACKEND", "libsql"),
+            ("ONBOARD_COMPLETED", "true"),
+        ];
+        let mut content = String::new();
+        for (key, value) in &vars {
+            let escaped = value.replace('\\', "\\\\").replace('"', "\\\"");
+            content.push_str(&format!("{}=\"{}\"\n", key, escaped));
+        }
+        std::fs::write(&env_path, &content).unwrap();
+
+        // Verify dotenvy parses ONBOARD_COMPLETED correctly
+        let parsed: Vec<(String, String)> = dotenvy::from_path_iter(&env_path)
+            .unwrap()
+            .filter_map(|r| r.ok())
+            .collect();
+        assert_eq!(parsed.len(), 2);
+        let onboard = parsed.iter().find(|(k, _)| k == "ONBOARD_COMPLETED");
+        assert!(onboard.is_some(), "ONBOARD_COMPLETED must be present");
+        assert_eq!(onboard.unwrap().1, "true");
+    }
 }

src/channels/http.rs

@@ -12,6 +12,7 @@ use axum::{
 };
 use secrecy::ExposeSecret;
 use serde::{Deserialize, Serialize};
+use subtle::ConstantTimeEq;
 use tokio::sync::{RwLock, mpsc, oneshot};
 use tokio_stream::wrappers::ReceiverStream;
 use uuid::Uuid;
@@ -173,7 +174,7 @@ async fn webhook_handler(
     // Validate secret if configured
     if let Some(ref expected_secret) = state.webhook_secret {
         match &req.secret {
-            Some(provided) if provided == expected_secret => {
+            Some(provided) if bool::from(provided.as_bytes().ct_eq(expected_secret.as_bytes())) => {
                 // Secret matches, continue
             }
             Some(_) => {
@@ -356,19 +357,89 @@ impl Channel for HttpChannel {
 
 #[cfg(test)]
 mod tests {
+    use axum::body::Body;
+    use axum::http::Request;
+    use secrecy::SecretString;
+    use tower::ServiceExt;
+
     use super::*;
 
+    fn test_channel(secret: Option<&str>) -> HttpChannel {
+        HttpChannel::new(HttpConfig {
+            host: "127.0.0.1".to_string(),
+            port: 0,
+            webhook_secret: secret.map(|s| SecretString::from(s.to_string())),
+            user_id: "http".to_string(),
+        })
+    }
+
     #[tokio::test]
     async fn test_http_channel_requires_secret() {
-        let config = HttpConfig {
-            host: "127.0.0.1".to_string(),
-            port: 0,
-            webhook_secret: None,
-            user_id: "http".to_string(),
-        };
-
-        let channel = HttpChannel::new(config);
+        let channel = test_channel(None);
         let result = channel.start().await;
         assert!(result.is_err());
     }
+
+    #[tokio::test]
+    async fn webhook_correct_secret_returns_ok() {
+        let channel = test_channel(Some("test-secret-123"));
+        // Start the channel so the tx sender is populated (otherwise 503).
+        let _stream = channel.start().await.unwrap();
+        let app = channel.routes();
+
+        let body = serde_json::json!({
+            "content": "hello",
+            "secret": "test-secret-123"
+        });
+        let req = Request::builder()
+            .method("POST")
+            .uri("/webhook")
+            .header("content-type", "application/json")
+            .body(Body::from(serde_json::to_vec(&body).unwrap()))
+            .unwrap();
+
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::OK);
+    }
+
+    #[tokio::test]
+    async fn webhook_wrong_secret_returns_unauthorized() {
+        let channel = test_channel(Some("correct-secret"));
+        let _stream = channel.start().await.unwrap();
+        let app = channel.routes();
+
+        let body = serde_json::json!({
+            "content": "hello",
+            "secret": "wrong-secret"
+        });
+        let req = Request::builder()
+            .method("POST")
+            .uri("/webhook")
+            .header("content-type", "application/json")
+            .body(Body::from(serde_json::to_vec(&body).unwrap()))
+            .unwrap();
+
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::UNAUTHORIZED);
+    }
+
+    #[tokio::test]
+    async fn webhook_missing_secret_returns_unauthorized() {
+        let channel = test_channel(Some("correct-secret"));
+        let _stream = channel.start().await.unwrap();
+        let app = channel.routes();
+
+        let body = serde_json::json!({
+            "content": "hello"
+        });
+        let req = Request::builder()
+            .method("POST")
+            .uri("/webhook")
+            .header("content-type", "application/json")
+            .body(Body::from(serde_json::to_vec(&body).unwrap()))
+            .unwrap();
+
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::UNAUTHORIZED);
+    }
 }

src/channels/manager.rs

@@ -4,24 +4,41 @@ use std::collections::HashMap;
 use std::sync::Arc;
 
 use futures::stream;
-use tokio::sync::RwLock;
+use tokio::sync::{RwLock, mpsc};
 
 use crate::channels::{Channel, IncomingMessage, MessageStream, OutgoingResponse, StatusUpdate};
 use crate::error::ChannelError;
 
 /// Manages multiple input channels and merges their message streams.
+///
+/// Includes an injection channel so background tasks (e.g., job monitors) can
+/// push messages into the agent loop without being a full `Channel` impl.
 pub struct ChannelManager {
     channels: Arc<RwLock<HashMap<String, Box<dyn Channel>>>>,
+    inject_tx: mpsc::Sender<IncomingMessage>,
+    /// Taken once in `start_all()` and merged into the stream.
+    inject_rx: tokio::sync::Mutex<Option<mpsc::Receiver<IncomingMessage>>>,
 }
 
 impl ChannelManager {
     /// Create a new channel manager.
     pub fn new() -> Self {
+        let (inject_tx, inject_rx) = mpsc::channel(64);
         Self {
             channels: Arc::new(RwLock::new(HashMap::new())),
+            inject_tx,
+            inject_rx: tokio::sync::Mutex::new(Some(inject_rx)),
         }
     }
 
+    /// Get a clone of the injection sender.
+    ///
+    /// Background tasks (like job monitors) use this to push messages into the
+    /// agent loop without being a full `Channel` implementation.
+    pub fn inject_sender(&self) -> mpsc::Sender<IncomingMessage> {
+        self.inject_tx.clone()
+    }
+
     /// Add a channel to the manager.
     pub fn add(&mut self, channel: Box<dyn Channel>) {
         let name = channel.name().to_string();
@@ -36,9 +53,12 @@ impl ChannelManager {
     }
 
     /// Start all channels and return a merged stream of messages.
+    ///
+    /// Also merges the injection channel so background tasks can push messages
+    /// into the same stream.
     pub async fn start_all(&self) -> Result<MessageStream, ChannelError> {
         let channels = self.channels.read().await;
-        let mut streams = Vec::new();
+        let mut streams: Vec<MessageStream> = Vec::new();
 
         for (name, channel) in channels.iter() {
             match channel.start().await {
@@ -60,6 +80,13 @@ impl ChannelManager {
             });
         }
 
+        // Take the injection receiver (can only be taken once)
+        if let Some(inject_rx) = self.inject_rx.lock().await.take() {
+            let inject_stream = tokio_stream::wrappers::ReceiverStream::new(inject_rx);
+            streams.push(Box::pin(inject_stream));
+            tracing::debug!("Injection channel merged into message stream");
+        }
+
         // Merge all streams into one
         let merged = stream::select_all(streams);
         Ok(Box::pin(merged))

src/channels/repl.rs

@@ -330,7 +330,13 @@ impl Channel for ReplChannel {
                         // Handle local REPL commands (only commands that need
                         // immediate local handling stay here)
                         match line.to_lowercase().as_str() {
-                            "/quit" | "/exit" => break,
+                            "/quit" | "/exit" => {
+                                // Forward shutdown command so the agent loop exits even
+                                // when other channels (e.g. web gateway) are still active.
+                                let msg = IncomingMessage::new("repl", "default", "/quit");
+                                let _ = tx.blocking_send(msg);
+                                break;
+                            }
                             "/help" => {
                                 print_help();
                                 continue;

src/channels/wasm/host.rs

@@ -300,6 +300,51 @@ impl ChannelHostState {
     }
 }
 
+/// In-memory workspace store for WASM channels.
+///
+/// Persists workspace writes across callback invocations within a single
+/// channel lifetime. This allows WASM channels to maintain state (e.g.,
+/// Telegram polling offsets) between poll ticks without requiring a
+/// full database-backed workspace.
+///
+/// Uses `std::sync::RwLock` (not tokio) because WASM execution runs
+/// inside `spawn_blocking`.
+pub struct ChannelWorkspaceStore {
+    data: std::sync::RwLock<std::collections::HashMap<String, String>>,
+}
+
+impl ChannelWorkspaceStore {
+    /// Create a new empty workspace store.
+    pub fn new() -> Self {
+        Self {
+            data: std::sync::RwLock::new(std::collections::HashMap::new()),
+        }
+    }
+
+    /// Commit pending writes from a callback execution into the store.
+    pub fn commit_writes(&self, writes: &[PendingWorkspaceWrite]) {
+        if writes.is_empty() {
+            return;
+        }
+        if let Ok(mut data) = self.data.write() {
+            for write in writes {
+                tracing::debug!(
+                    path = %write.path,
+                    content_len = write.content.len(),
+                    "Committing workspace write to channel store"
+                );
+                data.insert(write.path.clone(), write.content.clone());
+            }
+        }
+    }
+}
+
+impl crate::tools::wasm::WorkspaceReader for ChannelWorkspaceStore {
+    fn read(&self, path: &str) -> Option<String> {
+        self.data.read().ok()?.get(path).cloned()
+    }
+}
+
 /// Rate limiter for channel message emission.
 ///
 /// Tracks emission rates across multiple executions.
@@ -497,4 +542,56 @@ mod tests {
 
         assert_eq!(state.channel_name(), "telegram");
     }
+
+    #[test]
+    fn test_channel_workspace_store_commit_and_read() {
+        use crate::channels::wasm::host::{ChannelWorkspaceStore, PendingWorkspaceWrite};
+        use crate::tools::wasm::WorkspaceReader;
+
+        let store = ChannelWorkspaceStore::new();
+
+        // Initially empty
+        assert!(store.read("channels/telegram/offset").is_none());
+
+        // Commit some writes
+        let writes = vec![
+            PendingWorkspaceWrite {
+                path: "channels/telegram/offset".to_string(),
+                content: "103".to_string(),
+            },
+            PendingWorkspaceWrite {
+                path: "channels/telegram/state.json".to_string(),
+                content: r#"{"ok":true}"#.to_string(),
+            },
+        ];
+        store.commit_writes(&writes);
+
+        // Should be readable
+        assert_eq!(
+            store.read("channels/telegram/offset"),
+            Some("103".to_string())
+        );
+        assert_eq!(
+            store.read("channels/telegram/state.json"),
+            Some(r#"{"ok":true}"#.to_string())
+        );
+
+        // Overwrite a value
+        let writes2 = vec![PendingWorkspaceWrite {
+            path: "channels/telegram/offset".to_string(),
+            content: "200".to_string(),
+        }];
+        store.commit_writes(&writes2);
+        assert_eq!(
+            store.read("channels/telegram/offset"),
+            Some("200".to_string())
+        );
+
+        // Empty writes are a no-op
+        store.commit_writes(&[]);
+        assert_eq!(
+            store.read("channels/telegram/offset"),
+            Some("200".to_string())
+        );
+    }
 }

src/channels/wasm/wrapper.rs

@@ -42,7 +42,9 @@ use wasmtime_wasi::{ResourceTable, WasiCtx, WasiCtxBuilder, WasiView};
 
 use crate::channels::wasm::capabilities::ChannelCapabilities;
 use crate::channels::wasm::error::WasmChannelError;
-use crate::channels::wasm::host::{ChannelEmitRateLimiter, ChannelHostState, EmittedMessage};
+use crate::channels::wasm::host::{
+    ChannelEmitRateLimiter, ChannelHostState, ChannelWorkspaceStore, EmittedMessage,
+};
 use crate::channels::wasm::router::RegisteredEndpoint;
 use crate::channels::wasm::runtime::{PreparedChannelModule, WasmChannelRuntime};
 use crate::channels::wasm::schema::ChannelConfig;
@@ -547,6 +549,10 @@ pub struct WasmChannel {
 
     /// Pairing store for DM pairing (guest access control).
     pairing_store: Arc<PairingStore>,
+
+    /// In-memory workspace store persisting writes across callback invocations.
+    /// Ensures WASM channels can maintain state (e.g., polling offsets) between ticks.
+    workspace_store: Arc<ChannelWorkspaceStore>,
 }
 
 impl WasmChannel {
@@ -577,6 +583,7 @@ impl WasmChannel {
             credentials: Arc::new(RwLock::new(HashMap::new())),
             typing_task: RwLock::new(None),
             pairing_store,
+            workspace_store: Arc::new(ChannelWorkspaceStore::new()),
         }
     }
 
@@ -634,6 +641,26 @@ impl WasmChannel {
         self.endpoints.read().await.clone()
     }
 
+    /// Inject the workspace store as the reader into a capabilities clone.
+    ///
+    /// Ensures `workspace_read` capability is present with the store as its reader,
+    /// so WASM callbacks can read previously written workspace state.
+    fn inject_workspace_reader(
+        capabilities: &ChannelCapabilities,
+        store: &Arc<ChannelWorkspaceStore>,
+    ) -> ChannelCapabilities {
+        let mut caps = capabilities.clone();
+        let ws_cap = caps
+            .tool_capabilities
+            .workspace_read
+            .get_or_insert_with(|| crate::tools::wasm::WorkspaceCapability {
+                allowed_prefixes: Vec::new(),
+                reader: None,
+            });
+        ws_cap.reader = Some(Arc::clone(store) as Arc<dyn crate::tools::wasm::WorkspaceReader>);
+        caps
+    }
+
     /// Add channel host functions to the linker using generated bindings.
     ///
     /// Uses the wasmtime::component::bindgen! generated `add_to_linker` function
@@ -765,12 +792,13 @@ impl WasmChannel {
 
         let runtime = Arc::clone(&self.runtime);
         let prepared = Arc::clone(&self.prepared);
-        let capabilities = self.capabilities.clone();
+        let capabilities = Self::inject_workspace_reader(&self.capabilities, &self.workspace_store);
         let config_json = self.config_json.read().await.clone();
         let timeout = self.runtime.config().callback_timeout;
         let channel_name = self.name.clone();
         let credentials = self.get_credentials().await;
         let pairing_store = self.pairing_store.clone();
+        let workspace_store = self.workspace_store.clone();
 
         // Execute in blocking task with timeout
         let result = tokio::time::timeout(timeout, async move {
@@ -801,8 +829,13 @@ impl WasmChannel {
                     }
                 };
 
-                let host_state =
+                let mut host_state =
                     Self::extract_host_state(&mut store, &prepared.name, &capabilities);
+
+                // Commit pending workspace writes to the persistent store
+                let pending_writes = host_state.take_pending_writes();
+                workspace_store.commit_writes(&pending_writes);
+
                 Ok((config, host_state))
             })
             .await
@@ -897,10 +930,11 @@ impl WasmChannel {
 
         let runtime = Arc::clone(&self.runtime);
         let prepared = Arc::clone(&self.prepared);
-        let capabilities = self.capabilities.clone();
+        let capabilities = Self::inject_workspace_reader(&self.capabilities, &self.workspace_store);
         let timeout = self.runtime.config().callback_timeout;
         let credentials = self.get_credentials().await;
         let pairing_store = self.pairing_store.clone();
+        let workspace_store = self.workspace_store.clone();
 
         // Prepare request data
         let method = method.to_string();
@@ -940,8 +974,13 @@ impl WasmChannel {
                     .map_err(|e| Self::map_wasm_error(e, &prepared.name, prepared.limits.fuel))?;
 
                 let response = convert_http_response(wit_response);
-                let host_state =
+                let mut host_state =
                     Self::extract_host_state(&mut store, &prepared.name, &capabilities);
+
+                // Commit pending workspace writes to the persistent store
+                let pending_writes = host_state.take_pending_writes();
+                workspace_store.commit_writes(&pending_writes);
+
                 Ok((response, host_state))
             })
             .await
@@ -989,11 +1028,12 @@ impl WasmChannel {
 
         let runtime = Arc::clone(&self.runtime);
         let prepared = Arc::clone(&self.prepared);
-        let capabilities = self.capabilities.clone();
+        let capabilities = Self::inject_workspace_reader(&self.capabilities, &self.workspace_store);
         let timeout = self.runtime.config().callback_timeout;
         let channel_name = self.name.clone();
         let credentials = self.get_credentials().await;
         let pairing_store = self.pairing_store.clone();
+        let workspace_store = self.workspace_store.clone();
 
         // Execute in blocking task with timeout
         let result = tokio::time::timeout(timeout, async move {
@@ -1013,8 +1053,13 @@ impl WasmChannel {
                     .call_on_poll(&mut store)
                     .map_err(|e| Self::map_wasm_error(e, &prepared.name, prepared.limits.fuel))?;
 
-                let host_state =
+                let mut host_state =
                     Self::extract_host_state(&mut store, &prepared.name, &capabilities);
+
+                // Commit pending workspace writes to the persistent store
+                let pending_writes = host_state.take_pending_writes();
+                workspace_store.commit_writes(&pending_writes);
+
                 Ok(((), host_state))
             })
             .await
@@ -1501,6 +1546,7 @@ impl WasmChannel {
         let credentials = self.credentials.clone();
         let pairing_store = self.pairing_store.clone();
         let callback_timeout = self.runtime.config().callback_timeout;
+        let workspace_store = self.workspace_store.clone();
 
         tokio::spawn(async move {
             let mut interval_timer = tokio::time::interval(interval);
@@ -1523,6 +1569,7 @@ impl WasmChannel {
                             &credentials,
                             pairing_store.clone(),
                             callback_timeout,
+                            &workspace_store,
                         ).await;
 
                         match result {
@@ -1565,7 +1612,10 @@ impl WasmChannel {
 
     /// Execute a single poll callback with a fresh WASM instance.
     ///
-    /// Returns any emitted messages from the callback.
+    /// Returns any emitted messages from the callback. Pending workspace writes
+    /// are committed to the shared `ChannelWorkspaceStore` so state persists
+    /// across poll ticks (e.g., Telegram polling offset).
+    #[allow(clippy::too_many_arguments)]
     async fn execute_poll(
         channel_name: &str,
         runtime: &Arc<WasmChannelRuntime>,
@@ -1574,6 +1624,7 @@ impl WasmChannel {
         credentials: &RwLock<HashMap<String, String>>,
         pairing_store: Arc<PairingStore>,
         timeout: Duration,
+        workspace_store: &Arc<ChannelWorkspaceStore>,
     ) -> Result<Vec<EmittedMessage>, WasmChannelError> {
         // Skip if no WASM bytes (testing mode)
         if prepared.component_bytes.is_empty() {
@@ -1586,9 +1637,10 @@ impl WasmChannel {
 
         let runtime = Arc::clone(runtime);
         let prepared = Arc::clone(prepared);
-        let capabilities = capabilities.clone();
+        let capabilities = Self::inject_workspace_reader(capabilities, workspace_store);
         let credentials_snapshot = credentials.read().await.clone();
         let channel_name_owned = channel_name.to_string();
+        let workspace_store = Arc::clone(workspace_store);
 
         // Execute in blocking task with timeout
         let result = tokio::time::timeout(timeout, async move {
@@ -1608,8 +1660,13 @@ impl WasmChannel {
                     .call_on_poll(&mut store)
                     .map_err(|e| Self::map_wasm_error(e, &prepared.name, prepared.limits.fuel))?;
 
-                let host_state =
+                let mut host_state =
                     Self::extract_host_state(&mut store, &prepared.name, &capabilities);
+
+                // Commit pending workspace writes to the persistent store
+                let pending_writes = host_state.take_pending_writes();
+                workspace_store.commit_writes(&pending_writes);
+
                 Ok(host_state)
             })
             .await
@@ -2230,6 +2287,8 @@ mod tests {
         let credentials = Arc::new(tokio::sync::RwLock::new(std::collections::HashMap::new()));
         let timeout = std::time::Duration::from_secs(5);
 
+        let workspace_store = Arc::new(crate::channels::wasm::host::ChannelWorkspaceStore::new());
+
         let result = WasmChannel::execute_poll(
             "poll-test",
             &runtime,
@@ -2238,6 +2297,7 @@ mod tests {
             &credentials,
             Arc::new(PairingStore::new()),
             timeout,
+            &workspace_store,
         )
         .await;
 

src/channels/web/handlers/chat.rs

@@ -0,0 +1,633 @@
+//! Chat handlers: send, approval, auth, SSE events, WebSocket, history, threads.
+
+use std::sync::Arc;
+
+use axum::{
+    Json,
+    extract::{Query, State, WebSocketUpgrade},
+    http::StatusCode,
+    response::IntoResponse,
+};
+use serde::Deserialize;
+use uuid::Uuid;
+
+use crate::channels::IncomingMessage;
+use crate::channels::web::server::GatewayState;
+use crate::channels::web::types::*;
+
+pub async fn chat_send_handler(
+    State(state): State<Arc<GatewayState>>,
+    Json(req): Json<SendMessageRequest>,
+) -> Result<(StatusCode, Json<SendMessageResponse>), (StatusCode, String)> {
+    if !state.chat_rate_limiter.check() {
+        return Err((
+            StatusCode::TOO_MANY_REQUESTS,
+            "Rate limit exceeded. Try again shortly.".to_string(),
+        ));
+    }
+
+    let mut msg = IncomingMessage::new("gateway", &state.user_id, &req.content);
+
+    if let Some(ref thread_id) = req.thread_id {
+        msg = msg.with_thread(thread_id);
+        msg = msg.with_metadata(serde_json::json!({"thread_id": thread_id}));
+    }
+
+    let msg_id = msg.id;
+
+    let tx_guard = state.msg_tx.read().await;
+    let tx = tx_guard.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Channel not started".to_string(),
+    ))?;
+
+    tx.send(msg).await.map_err(|_| {
+        (
+            StatusCode::INTERNAL_SERVER_ERROR,
+            "Channel closed".to_string(),
+        )
+    })?;
+
+    Ok((
+        StatusCode::ACCEPTED,
+        Json(SendMessageResponse {
+            message_id: msg_id,
+            status: "accepted",
+        }),
+    ))
+}
+
+pub async fn chat_approval_handler(
+    State(state): State<Arc<GatewayState>>,
+    Json(req): Json<ApprovalRequest>,
+) -> Result<(StatusCode, Json<SendMessageResponse>), (StatusCode, String)> {
+    let (approved, always) = match req.action.as_str() {
+        "approve" => (true, false),
+        "always" => (true, true),
+        "deny" => (false, false),
+        other => {
+            return Err((
+                StatusCode::BAD_REQUEST,
+                format!("Unknown action: {}", other),
+            ));
+        }
+    };
+
+    let request_id = Uuid::parse_str(&req.request_id).map_err(|_| {
+        (
+            StatusCode::BAD_REQUEST,
+            "Invalid request_id (expected UUID)".to_string(),
+        )
+    })?;
+
+    // Build a structured ExecApproval submission as JSON, sent through the
+    // existing message pipeline so the agent loop picks it up.
+    let approval = crate::agent::submission::Submission::ExecApproval {
+        request_id,
+        approved,
+        always,
+    };
+    let content = serde_json::to_string(&approval).map_err(|e| {
+        (
+            StatusCode::INTERNAL_SERVER_ERROR,
+            format!("Failed to serialize approval: {}", e),
+        )
+    })?;
+
+    let mut msg = IncomingMessage::new("gateway", &state.user_id, content);
+
+    if let Some(ref thread_id) = req.thread_id {
+        msg = msg.with_thread(thread_id);
+    }
+
+    let msg_id = msg.id;
+
+    let tx_guard = state.msg_tx.read().await;
+    let tx = tx_guard.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Channel not started".to_string(),
+    ))?;
+
+    tx.send(msg).await.map_err(|_| {
+        (
+            StatusCode::INTERNAL_SERVER_ERROR,
+            "Channel closed".to_string(),
+        )
+    })?;
+
+    Ok((
+        StatusCode::ACCEPTED,
+        Json(SendMessageResponse {
+            message_id: msg_id,
+            status: "accepted",
+        }),
+    ))
+}
+
+/// Submit an auth token directly to the extension manager, bypassing the message pipeline.
+///
+/// The token never touches the LLM, chat history, or SSE stream.
+pub async fn chat_auth_token_handler(
+    State(state): State<Arc<GatewayState>>,
+    Json(req): Json<AuthTokenRequest>,
+) -> Result<Json<ActionResponse>, (StatusCode, String)> {
+    let ext_mgr = state.extension_manager.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Extension manager not available".to_string(),
+    ))?;
+
+    let result = ext_mgr
+        .auth(&req.extension_name, Some(&req.token))
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    if result.status == "authenticated" {
+        // Auto-activate so tools are available immediately
+        let msg = match ext_mgr.activate(&req.extension_name).await {
+            Ok(r) => format!(
+                "{} authenticated ({} tools loaded)",
+                req.extension_name,
+                r.tools_loaded.len()
+            ),
+            Err(e) => format!(
+                "{} authenticated but activation failed: {}",
+                req.extension_name, e
+            ),
+        };
+
+        // Clear auth mode on the active thread
+        clear_auth_mode(&state).await;
+
+        state.sse.broadcast(SseEvent::AuthCompleted {
+            extension_name: req.extension_name,
+            success: true,
+            message: msg.clone(),
+        });
+
+        Ok(Json(ActionResponse::ok(msg)))
+    } else {
+        // Re-emit auth_required for retry
+        state.sse.broadcast(SseEvent::AuthRequired {
+            extension_name: req.extension_name.clone(),
+            instructions: result.instructions.clone(),
+            auth_url: result.auth_url.clone(),
+            setup_url: result.setup_url.clone(),
+        });
+        Ok(Json(ActionResponse::fail(
+            result
+                .instructions
+                .unwrap_or_else(|| "Invalid token".to_string()),
+        )))
+    }
+}
+
+/// Cancel an in-progress auth flow.
+pub async fn chat_auth_cancel_handler(
+    State(state): State<Arc<GatewayState>>,
+    Json(_req): Json<AuthCancelRequest>,
+) -> Result<Json<ActionResponse>, (StatusCode, String)> {
+    clear_auth_mode(&state).await;
+    Ok(Json(ActionResponse::ok("Auth cancelled")))
+}
+
+/// Clear pending auth mode on the active thread.
+pub async fn clear_auth_mode(state: &GatewayState) {
+    if let Some(ref sm) = state.session_manager {
+        let session = sm.get_or_create_session(&state.user_id).await;
+        let mut sess = session.lock().await;
+        if let Some(thread_id) = sess.active_thread
+            && let Some(thread) = sess.threads.get_mut(&thread_id)
+        {
+            thread.pending_auth = None;
+        }
+    }
+}
+
+pub async fn chat_events_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<impl IntoResponse, (StatusCode, String)> {
+    state.sse.subscribe().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Too many connections".to_string(),
+    ))
+}
+
+pub async fn chat_ws_handler(
+    headers: axum::http::HeaderMap,
+    ws: WebSocketUpgrade,
+    State(state): State<Arc<GatewayState>>,
+) -> Result<impl IntoResponse, (StatusCode, String)> {
+    // Validate Origin header to prevent cross-site WebSocket hijacking.
+    let origin = headers
+        .get("origin")
+        .and_then(|v| v.to_str().ok())
+        .ok_or_else(|| {
+            (
+                StatusCode::FORBIDDEN,
+                "WebSocket Origin header required".to_string(),
+            )
+        })?;
+
+    let host = origin
+        .strip_prefix("http://")
+        .or_else(|| origin.strip_prefix("https://"))
+        .and_then(|rest| rest.split(':').next()?.split('/').next())
+        .unwrap_or("");
+
+    let is_local = matches!(host, "localhost" | "127.0.0.1" | "[::1]");
+    if !is_local {
+        return Err((
+            StatusCode::FORBIDDEN,
+            "WebSocket origin not allowed".to_string(),
+        ));
+    }
+    Ok(ws.on_upgrade(move |socket| crate::channels::web::ws::handle_ws_connection(socket, state)))
+}
+
+#[derive(Deserialize)]
+pub struct HistoryQuery {
+    pub thread_id: Option<String>,
+    pub limit: Option<usize>,
+    pub before: Option<String>,
+}
+
+pub async fn chat_history_handler(
+    State(state): State<Arc<GatewayState>>,
+    Query(query): Query<HistoryQuery>,
+) -> Result<Json<HistoryResponse>, (StatusCode, String)> {
+    let session_manager = state.session_manager.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Session manager not available".to_string(),
+    ))?;
+
+    let session = session_manager.get_or_create_session(&state.user_id).await;
+    let sess = session.lock().await;
+
+    let limit = query.limit.unwrap_or(50);
+    let before_cursor = query
+        .before
+        .as_deref()
+        .map(|s| {
+            chrono::DateTime::parse_from_rfc3339(s)
+                .map(|dt| dt.with_timezone(&chrono::Utc))
+                .map_err(|_| {
+                    (
+                        StatusCode::BAD_REQUEST,
+                        "Invalid 'before' timestamp".to_string(),
+                    )
+                })
+        })
+        .transpose()?;
+
+    // Find the thread
+    let thread_id = if let Some(ref tid) = query.thread_id {
+        Uuid::parse_str(tid)
+            .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid thread_id".to_string()))?
+    } else {
+        sess.active_thread
+            .ok_or((StatusCode::NOT_FOUND, "No active thread".to_string()))?
+    };
+
+    // Verify the thread belongs to the authenticated user before returning any data.
+    if query.thread_id.is_some()
+        && let Some(ref store) = state.store
+    {
+        let owned = store
+            .conversation_belongs_to_user(thread_id, &state.user_id)
+            .await
+            .unwrap_or(false);
+        if !owned && !sess.threads.contains_key(&thread_id) {
+            return Err((StatusCode::NOT_FOUND, "Thread not found".to_string()));
+        }
+    }
+
+    // For paginated requests (before cursor set), always go to DB
+    if before_cursor.is_some()
+        && let Some(ref store) = state.store
+    {
+        let (messages, has_more) = store
+            .list_conversation_messages_paginated(thread_id, before_cursor, limit as i64)
+            .await
+            .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+        let oldest_timestamp = messages.first().map(|m| m.created_at.to_rfc3339());
+        let turns = build_turns_from_db_messages(&messages);
+        return Ok(Json(HistoryResponse {
+            thread_id,
+            turns,
+            has_more,
+            oldest_timestamp,
+        }));
+    }
+
+    // Try in-memory first (freshest data for active threads)
+    if let Some(thread) = sess.threads.get(&thread_id)
+        && !thread.turns.is_empty()
+    {
+        let turns: Vec<TurnInfo> = thread
+            .turns
+            .iter()
+            .map(|t| TurnInfo {
+                turn_number: t.turn_number,
+                user_input: t.user_input.clone(),
+                response: t.response.clone(),
+                state: format!("{:?}", t.state),
+                started_at: t.started_at.to_rfc3339(),
+                completed_at: t.completed_at.map(|dt| dt.to_rfc3339()),
+                tool_calls: t
+                    .tool_calls
+                    .iter()
+                    .map(|tc| ToolCallInfo {
+                        name: tc.name.clone(),
+                        has_result: tc.result.is_some(),
+                        has_error: tc.error.is_some(),
+                    })
+                    .collect(),
+            })
+            .collect();
+
+        return Ok(Json(HistoryResponse {
+            thread_id,
+            turns,
+            has_more: false,
+            oldest_timestamp: None,
+        }));
+    }
+
+    // Fall back to DB for historical threads not in memory (paginated)
+    if let Some(ref store) = state.store {
+        let (messages, has_more) = store
+            .list_conversation_messages_paginated(thread_id, None, limit as i64)
+            .await
+            .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+        if !messages.is_empty() {
+            let oldest_timestamp = messages.first().map(|m| m.created_at.to_rfc3339());
+            let turns = build_turns_from_db_messages(&messages);
+            return Ok(Json(HistoryResponse {
+                thread_id,
+                turns,
+                has_more,
+                oldest_timestamp,
+            }));
+        }
+    }
+
+    // Empty thread (just created, no messages yet)
+    Ok(Json(HistoryResponse {
+        thread_id,
+        turns: Vec::new(),
+        has_more: false,
+        oldest_timestamp: None,
+    }))
+}
+
+/// Build TurnInfo pairs from flat DB messages (alternating user/assistant).
+pub fn build_turns_from_db_messages(
+    messages: &[crate::history::ConversationMessage],
+) -> Vec<TurnInfo> {
+    let mut turns = Vec::new();
+    let mut turn_number = 0;
+    let mut iter = messages.iter().peekable();
+
+    while let Some(msg) = iter.next() {
+        if msg.role == "user" {
+            let mut turn = TurnInfo {
+                turn_number,
+                user_input: msg.content.clone(),
+                response: None,
+                state: "Completed".to_string(),
+                started_at: msg.created_at.to_rfc3339(),
+                completed_at: None,
+                tool_calls: Vec::new(),
+            };
+
+            // Check if next message is an assistant response
+            if let Some(next) = iter.peek()
+                && next.role == "assistant"
+            {
+                let assistant_msg = iter.next().expect("peeked");
+                turn.response = Some(assistant_msg.content.clone());
+                turn.completed_at = Some(assistant_msg.created_at.to_rfc3339());
+            }
+
+            // Incomplete turn (user message without response)
+            if turn.response.is_none() {
+                turn.state = "Failed".to_string();
+            }
+
+            turns.push(turn);
+            turn_number += 1;
+        }
+    }
+
+    turns
+}
+
+pub async fn chat_threads_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<Json<ThreadListResponse>, (StatusCode, String)> {
+    let session_manager = state.session_manager.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Session manager not available".to_string(),
+    ))?;
+
+    let session = session_manager.get_or_create_session(&state.user_id).await;
+    let sess = session.lock().await;
+
+    // Try DB first for persistent thread list
+    if let Some(ref store) = state.store {
+        // Auto-create assistant thread if it doesn't exist
+        let assistant_id = store
+            .get_or_create_assistant_conversation(&state.user_id, "gateway")
+            .await
+            .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+        if let Ok(summaries) = store
+            .list_conversations_with_preview(&state.user_id, "gateway", 50)
+            .await
+        {
+            let mut assistant_thread = None;
+            let mut threads = Vec::new();
+
+            for s in &summaries {
+                let info = ThreadInfo {
+                    id: s.id,
+                    state: "Idle".to_string(),
+                    turn_count: (s.message_count / 2).max(0) as usize,
+                    created_at: s.started_at.to_rfc3339(),
+                    updated_at: s.last_activity.to_rfc3339(),
+                    title: s.title.clone(),
+                    thread_type: s.thread_type.clone(),
+                };
+
+                if s.id == assistant_id {
+                    assistant_thread = Some(info);
+                } else {
+                    threads.push(info);
+                }
+            }
+
+            // If assistant wasn't in the list (0 messages), synthesize it
+            if assistant_thread.is_none() {
+                assistant_thread = Some(ThreadInfo {
+                    id: assistant_id,
+                    state: "Idle".to_string(),
+                    turn_count: 0,
+                    created_at: chrono::Utc::now().to_rfc3339(),
+                    updated_at: chrono::Utc::now().to_rfc3339(),
+                    title: None,
+                    thread_type: Some("assistant".to_string()),
+                });
+            }
+
+            return Ok(Json(ThreadListResponse {
+                assistant_thread,
+                threads,
+                active_thread: sess.active_thread,
+            }));
+        }
+    }
+
+    // Fallback: in-memory only (no assistant thread without DB)
+    let threads: Vec<ThreadInfo> = sess
+        .threads
+        .values()
+        .map(|t| ThreadInfo {
+            id: t.id,
+            state: format!("{:?}", t.state),
+            turn_count: t.turns.len(),
+            created_at: t.created_at.to_rfc3339(),
+            updated_at: t.updated_at.to_rfc3339(),
+            title: None,
+            thread_type: None,
+        })
+        .collect();
+
+    Ok(Json(ThreadListResponse {
+        assistant_thread: None,
+        threads,
+        active_thread: sess.active_thread,
+    }))
+}
+
+pub async fn chat_new_thread_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<Json<ThreadInfo>, (StatusCode, String)> {
+    let session_manager = state.session_manager.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Session manager not available".to_string(),
+    ))?;
+
+    let session = session_manager.get_or_create_session(&state.user_id).await;
+    let mut sess = session.lock().await;
+    let thread = sess.create_thread();
+    let thread_id = thread.id;
+    let info = ThreadInfo {
+        id: thread.id,
+        state: format!("{:?}", thread.state),
+        turn_count: thread.turns.len(),
+        created_at: thread.created_at.to_rfc3339(),
+        updated_at: thread.updated_at.to_rfc3339(),
+        title: None,
+        thread_type: Some("thread".to_string()),
+    };
+
+    // Persist the empty conversation row with thread_type metadata
+    if let Some(ref store) = state.store {
+        let store = Arc::clone(store);
+        let user_id = state.user_id.clone();
+        tokio::spawn(async move {
+            if let Err(e) = store
+                .ensure_conversation(thread_id, "gateway", &user_id, None)
+                .await
+            {
+                tracing::warn!("Failed to persist new thread: {}", e);
+            }
+            let metadata_val = serde_json::json!("thread");
+            if let Err(e) = store
+                .update_conversation_metadata_field(thread_id, "thread_type", &metadata_val)
+                .await
+            {
+                tracing::warn!("Failed to set thread_type metadata: {}", e);
+            }
+        });
+    }
+
+    Ok(Json(info))
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn test_build_turns_from_db_messages_complete() {
+        let now = chrono::Utc::now();
+        let messages = vec![
+            crate::history::ConversationMessage {
+                id: Uuid::new_v4(),
+                role: "user".to_string(),
+                content: "Hello".to_string(),
+                created_at: now,
+            },
+            crate::history::ConversationMessage {
+                id: Uuid::new_v4(),
+                role: "assistant".to_string(),
+                content: "Hi there!".to_string(),
+                created_at: now + chrono::TimeDelta::seconds(1),
+            },
+            crate::history::ConversationMessage {
+                id: Uuid::new_v4(),
+                role: "user".to_string(),
+                content: "How are you?".to_string(),
+                created_at: now + chrono::TimeDelta::seconds(2),
+            },
+            crate::history::ConversationMessage {
+                id: Uuid::new_v4(),
+                role: "assistant".to_string(),
+                content: "Doing well!".to_string(),
+                created_at: now + chrono::TimeDelta::seconds(3),
+            },
+        ];
+
+        let turns = build_turns_from_db_messages(&messages);
+        assert_eq!(turns.len(), 2);
+        assert_eq!(turns[0].user_input, "Hello");
+        assert_eq!(turns[0].response.as_deref(), Some("Hi there!"));
+        assert_eq!(turns[0].state, "Completed");
+        assert_eq!(turns[1].user_input, "How are you?");
+        assert_eq!(turns[1].response.as_deref(), Some("Doing well!"));
+    }
+
+    #[test]
+    fn test_build_turns_from_db_messages_incomplete_last() {
+        let now = chrono::Utc::now();
+        let messages = vec![
+            crate::history::ConversationMessage {
+                id: Uuid::new_v4(),
+                role: "user".to_string(),
+                content: "Hello".to_string(),
+                created_at: now,
+            },
+            crate::history::ConversationMessage {
+                id: Uuid::new_v4(),
+                role: "assistant".to_string(),
+                content: "Hi!".to_string(),
+                created_at: now + chrono::TimeDelta::seconds(1),
+            },
+            crate::history::ConversationMessage {
+                id: Uuid::new_v4(),
+                role: "user".to_string(),
+                content: "Lost message".to_string(),
+                created_at: now + chrono::TimeDelta::seconds(2),
+            },
+        ];
+
+        let turns = build_turns_from_db_messages(&messages);
+        assert_eq!(turns.len(), 2);
+        assert_eq!(turns[1].user_input, "Lost message");
+        assert!(turns[1].response.is_none());
+        assert_eq!(turns[1].state, "Failed");
+    }
+}

src/channels/web/handlers/extensions.rs

@@ -0,0 +1,153 @@
+//! Extension management API handlers.
+
+use std::sync::Arc;
+
+use axum::{
+    Json,
+    extract::{Path, State},
+    http::StatusCode,
+};
+
+use crate::channels::web::server::GatewayState;
+use crate::channels::web::types::*;
+
+pub async fn extensions_list_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<Json<ExtensionListResponse>, (StatusCode, String)> {
+    let ext_mgr = state.extension_manager.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Extension manager not available (secrets store required)".to_string(),
+    ))?;
+
+    let installed = ext_mgr
+        .list(None)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    let extensions = installed
+        .into_iter()
+        .map(|ext| ExtensionInfo {
+            name: ext.name,
+            kind: ext.kind.to_string(),
+            description: ext.description,
+            url: ext.url,
+            authenticated: ext.authenticated,
+            active: ext.active,
+            tools: ext.tools,
+        })
+        .collect();
+
+    Ok(Json(ExtensionListResponse { extensions }))
+}
+
+pub async fn extensions_tools_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<Json<ToolListResponse>, (StatusCode, String)> {
+    let registry = state.tool_registry.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Tool registry not available".to_string(),
+    ))?;
+
+    let definitions = registry.tool_definitions().await;
+    let tools = definitions
+        .into_iter()
+        .map(|td| ToolInfo {
+            name: td.name,
+            description: td.description,
+        })
+        .collect();
+
+    Ok(Json(ToolListResponse { tools }))
+}
+
+pub async fn extensions_install_handler(
+    State(state): State<Arc<GatewayState>>,
+    Json(req): Json<InstallExtensionRequest>,
+) -> Result<Json<ActionResponse>, (StatusCode, String)> {
+    let ext_mgr = state.extension_manager.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Extension manager not available (secrets store required)".to_string(),
+    ))?;
+
+    let kind_hint = req.kind.as_deref().and_then(|k| match k {
+        "mcp_server" => Some(crate::extensions::ExtensionKind::McpServer),
+        "wasm_tool" => Some(crate::extensions::ExtensionKind::WasmTool),
+        "wasm_channel" => Some(crate::extensions::ExtensionKind::WasmChannel),
+        _ => None,
+    });
+
+    match ext_mgr
+        .install(&req.name, req.url.as_deref(), kind_hint)
+        .await
+    {
+        Ok(result) => Ok(Json(ActionResponse::ok(result.message))),
+        Err(e) => Ok(Json(ActionResponse::fail(e.to_string()))),
+    }
+}
+
+pub async fn extensions_activate_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(name): Path<String>,
+) -> Result<Json<ActionResponse>, (StatusCode, String)> {
+    let ext_mgr = state.extension_manager.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Extension manager not available (secrets store required)".to_string(),
+    ))?;
+
+    match ext_mgr.activate(&name).await {
+        Ok(result) => Ok(Json(ActionResponse::ok(result.message))),
+        Err(activate_err) => {
+            let err_str = activate_err.to_string();
+            let needs_auth = err_str.contains("authentication")
+                || err_str.contains("401")
+                || err_str.contains("Unauthorized");
+
+            if !needs_auth {
+                return Ok(Json(ActionResponse::fail(err_str)));
+            }
+
+            // Activation failed due to auth; try authenticating first.
+            match ext_mgr.auth(&name, None).await {
+                Ok(auth_result) if auth_result.status == "authenticated" => {
+                    // Auth succeeded, retry activation.
+                    match ext_mgr.activate(&name).await {
+                        Ok(result) => Ok(Json(ActionResponse::ok(result.message))),
+                        Err(e) => Ok(Json(ActionResponse::fail(e.to_string()))),
+                    }
+                }
+                Ok(auth_result) => {
+                    // Auth in progress (OAuth URL or awaiting manual token).
+                    let mut resp = ActionResponse::fail(
+                        auth_result
+                            .instructions
+                            .clone()
+                            .unwrap_or_else(|| format!("'{}' requires authentication.", name)),
+                    );
+                    resp.auth_url = auth_result.auth_url;
+                    resp.awaiting_token = Some(auth_result.awaiting_token);
+                    resp.instructions = auth_result.instructions;
+                    Ok(Json(resp))
+                }
+                Err(auth_err) => Ok(Json(ActionResponse::fail(format!(
+                    "Authentication failed: {}",
+                    auth_err
+                )))),
+            }
+        }
+    }
+}
+
+pub async fn extensions_remove_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(name): Path<String>,
+) -> Result<Json<ActionResponse>, (StatusCode, String)> {
+    let ext_mgr = state.extension_manager.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Extension manager not available (secrets store required)".to_string(),
+    ))?;
+
+    match ext_mgr.remove(&name).await {
+        Ok(message) => Ok(Json(ActionResponse::ok(message))),
+        Err(e) => Ok(Json(ActionResponse::fail(e.to_string()))),
+    }
+}

src/channels/web/handlers/jobs.rs

@@ -0,0 +1,518 @@
+//! Job and sandbox API handlers.
+
+use std::sync::Arc;
+
+use axum::{
+    Json,
+    extract::{Path, Query, State},
+    http::StatusCode,
+};
+use serde::Deserialize;
+use uuid::Uuid;
+
+use crate::channels::web::server::GatewayState;
+use crate::channels::web::types::*;
+
+pub async fn jobs_list_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<Json<JobListResponse>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    // Fetch sandbox jobs scoped to the authenticated user.
+    let sandbox_jobs = store
+        .list_sandbox_jobs_for_user(&state.user_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    // Scope jobs to the authenticated user.
+    let mut jobs: Vec<JobInfo> = sandbox_jobs
+        .iter()
+        .filter(|j| j.user_id == state.user_id)
+        .map(|j| {
+            let ui_state = match j.status.as_str() {
+                "creating" => "pending",
+                "running" => "in_progress",
+                s => s,
+            };
+            JobInfo {
+                id: j.id,
+                title: j.task.clone(),
+                state: ui_state.to_string(),
+                user_id: j.user_id.clone(),
+                created_at: j.created_at.to_rfc3339(),
+                started_at: j.started_at.map(|dt| dt.to_rfc3339()),
+            }
+        })
+        .collect();
+
+    // Most recent first.
+    jobs.sort_by(|a, b| b.created_at.cmp(&a.created_at));
+
+    Ok(Json(JobListResponse { jobs }))
+}
+
+pub async fn jobs_summary_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<Json<JobSummaryResponse>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let s = store
+        .sandbox_job_summary_for_user(&state.user_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    Ok(Json(JobSummaryResponse {
+        total: s.total,
+        pending: s.creating,
+        in_progress: s.running,
+        completed: s.completed,
+        failed: s.failed + s.interrupted,
+        stuck: 0,
+    }))
+}
+
+pub async fn jobs_detail_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(id): Path<String>,
+) -> Result<Json<JobDetailResponse>, (StatusCode, String)> {
+    let job_id = Uuid::parse_str(&id)
+        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid job ID".to_string()))?;
+
+    // Try sandbox job from DB first, scoped to the authenticated user.
+    if let Some(ref store) = state.store
+        && let Ok(Some(job)) = store.get_sandbox_job(job_id).await
+    {
+        if job.user_id != state.user_id {
+            return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+        }
+        let browse_id = std::path::Path::new(&job.project_dir)
+            .file_name()
+            .map(|n| n.to_string_lossy().to_string())
+            .unwrap_or_else(|| job.id.to_string());
+
+        let ui_state = match job.status.as_str() {
+            "creating" => "pending",
+            "running" => "in_progress",
+            s => s,
+        };
+
+        let elapsed_secs = job.started_at.map(|start| {
+            let end = job.completed_at.unwrap_or_else(chrono::Utc::now);
+            (end - start).num_seconds().max(0) as u64
+        });
+
+        // Synthesize transitions from timestamps.
+        let mut transitions = Vec::new();
+        if let Some(started) = job.started_at {
+            transitions.push(TransitionInfo {
+                from: "creating".to_string(),
+                to: "running".to_string(),
+                timestamp: started.to_rfc3339(),
+                reason: None,
+            });
+        }
+        if let Some(completed) = job.completed_at {
+            transitions.push(TransitionInfo {
+                from: "running".to_string(),
+                to: job.status.clone(),
+                timestamp: completed.to_rfc3339(),
+                reason: job.failure_reason.clone(),
+            });
+        }
+
+        return Ok(Json(JobDetailResponse {
+            id: job.id,
+            title: job.task.clone(),
+            description: String::new(),
+            state: ui_state.to_string(),
+            user_id: job.user_id.clone(),
+            created_at: job.created_at.to_rfc3339(),
+            started_at: job.started_at.map(|dt| dt.to_rfc3339()),
+            completed_at: job.completed_at.map(|dt| dt.to_rfc3339()),
+            elapsed_secs,
+            project_dir: Some(job.project_dir.clone()),
+            browse_url: Some(format!("/projects/{}/", browse_id)),
+            job_mode: {
+                let mode = store.get_sandbox_job_mode(job.id).await.ok().flatten();
+                mode.filter(|m| m != "worker")
+            },
+            transitions,
+        }));
+    }
+
+    Err((StatusCode::NOT_FOUND, "Job not found".to_string()))
+}
+
+pub async fn jobs_cancel_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(id): Path<String>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let job_id = Uuid::parse_str(&id)
+        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid job ID".to_string()))?;
+
+    // Try sandbox job cancellation, scoped to the authenticated user.
+    if let Some(ref store) = state.store
+        && let Ok(Some(job)) = store.get_sandbox_job(job_id).await
+    {
+        if job.user_id != state.user_id {
+            return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+        }
+        if job.status == "running" || job.status == "creating" {
+            // Stop the container if we have a job manager.
+            if let Some(ref jm) = state.job_manager
+                && let Err(e) = jm.stop_job(job_id).await
+            {
+                tracing::warn!(job_id = %job_id, error = %e, "Failed to stop container during cancellation");
+            }
+            store
+                .update_sandbox_job_status(
+                    job_id,
+                    "failed",
+                    Some(false),
+                    Some("Cancelled by user"),
+                    None,
+                    Some(chrono::Utc::now()),
+                )
+                .await
+                .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+        }
+        return Ok(Json(serde_json::json!({
+            "status": "cancelled",
+            "job_id": job_id,
+        })));
+    }
+
+    Err((StatusCode::NOT_FOUND, "Job not found".to_string()))
+}
+
+pub async fn jobs_restart_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(id): Path<String>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+    let jm = state.job_manager.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Sandbox not enabled".to_string(),
+    ))?;
+
+    let old_job_id = Uuid::parse_str(&id)
+        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid job ID".to_string()))?;
+
+    let old_job = store
+        .get_sandbox_job(old_job_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "Job not found".to_string()))?;
+
+    // Scope to the authenticated user.
+    if old_job.user_id != state.user_id {
+        return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+    }
+
+    if old_job.status != "interrupted" && old_job.status != "failed" {
+        return Err((
+            StatusCode::CONFLICT,
+            format!("Cannot restart job in state '{}'", old_job.status),
+        ));
+    }
+
+    // Create a new job with the same task and project_dir.
+    let new_job_id = Uuid::new_v4();
+    let now = chrono::Utc::now();
+
+    let record = crate::history::SandboxJobRecord {
+        id: new_job_id,
+        task: old_job.task.clone(),
+        status: "creating".to_string(),
+        user_id: old_job.user_id.clone(),
+        project_dir: old_job.project_dir.clone(),
+        success: None,
+        failure_reason: None,
+        created_at: now,
+        started_at: None,
+        completed_at: None,
+        credential_grants_json: old_job.credential_grants_json.clone(),
+    };
+    store
+        .save_sandbox_job(&record)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    // Look up the original job's mode so the restart uses the same mode.
+    let mode = match store.get_sandbox_job_mode(old_job_id).await {
+        Ok(Some(m)) if m == "claude_code" => crate::orchestrator::job_manager::JobMode::ClaudeCode,
+        _ => crate::orchestrator::job_manager::JobMode::Worker,
+    };
+
+    // Restore credential grants from the original job so the restarted container
+    // has access to the same secrets.
+    let credential_grants: Vec<crate::orchestrator::auth::CredentialGrant> =
+        serde_json::from_str(&old_job.credential_grants_json).unwrap_or_else(|e| {
+            tracing::warn!(
+                job_id = %old_job.id,
+                "Failed to deserialize credential grants from stored job: {}. \
+                 Restarted job will have no credentials.",
+                e
+            );
+            vec![]
+        });
+
+    let project_dir = std::path::PathBuf::from(&old_job.project_dir);
+    let _token = jm
+        .create_job(
+            new_job_id,
+            &old_job.task,
+            Some(project_dir),
+            mode,
+            credential_grants,
+        )
+        .await
+        .map_err(|e| {
+            (
+                StatusCode::INTERNAL_SERVER_ERROR,
+                format!("Failed to create container: {}", e),
+            )
+        })?;
+
+    store
+        .update_sandbox_job_status(new_job_id, "running", None, None, Some(now), None)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    Ok(Json(serde_json::json!({
+        "status": "restarted",
+        "old_job_id": old_job_id,
+        "new_job_id": new_job_id,
+    })))
+}
+
+/// Submit a follow-up prompt to a running Claude Code sandbox job.
+pub async fn jobs_prompt_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(id): Path<String>,
+    Json(body): Json<serde_json::Value>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let prompt_queue = state.prompt_queue.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Claude Code not configured".to_string(),
+    ))?;
+
+    let job_id: uuid::Uuid = id
+        .parse()
+        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid job ID".to_string()))?;
+
+    // Verify user owns this job.
+    if let Some(ref store) = state.store
+        && !store
+            .sandbox_job_belongs_to_user(job_id, &state.user_id)
+            .await
+            .unwrap_or(false)
+    {
+        return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+    }
+
+    let content = body
+        .get("content")
+        .and_then(|v| v.as_str())
+        .ok_or((
+            StatusCode::BAD_REQUEST,
+            "Missing 'content' field".to_string(),
+        ))?
+        .to_string();
+
+    let done = body.get("done").and_then(|v| v.as_bool()).unwrap_or(false);
+
+    let prompt = crate::orchestrator::api::PendingPrompt { content, done };
+
+    {
+        let mut queue = prompt_queue.lock().await;
+        queue.entry(job_id).or_default().push_back(prompt);
+    }
+
+    Ok(Json(serde_json::json!({
+        "status": "queued",
+        "job_id": job_id.to_string(),
+    })))
+}
+
+/// Load persisted job events for a job (for history replay on page open).
+pub async fn jobs_events_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(id): Path<String>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Database not available".to_string(),
+    ))?;
+
+    let job_id: uuid::Uuid = id
+        .parse()
+        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid job ID".to_string()))?;
+
+    // Verify user owns this job.
+    if !store
+        .sandbox_job_belongs_to_user(job_id, &state.user_id)
+        .await
+        .unwrap_or(false)
+    {
+        return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+    }
+
+    let events = store
+        .list_job_events(job_id, None)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    let events_json: Vec<serde_json::Value> = events
+        .into_iter()
+        .map(|e| {
+            serde_json::json!({
+                "id": e.id,
+                "event_type": e.event_type,
+                "data": e.data,
+                "created_at": e.created_at.to_rfc3339(),
+            })
+        })
+        .collect();
+
+    Ok(Json(serde_json::json!({
+        "job_id": job_id.to_string(),
+        "events": events_json,
+    })))
+}
+
+// --- Project file handlers for sandbox jobs ---
+
+#[derive(Deserialize)]
+pub struct FilePathQuery {
+    pub path: Option<String>,
+}
+
+pub async fn job_files_list_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(id): Path<String>,
+    Query(query): Query<FilePathQuery>,
+) -> Result<Json<ProjectFilesResponse>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let job_id = Uuid::parse_str(&id)
+        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid job ID".to_string()))?;
+
+    let job = store
+        .get_sandbox_job(job_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "Job not found".to_string()))?;
+
+    // Verify user owns this job.
+    if job.user_id != state.user_id {
+        return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+    }
+
+    let base = std::path::PathBuf::from(&job.project_dir);
+    let rel_path = query.path.as_deref().unwrap_or("");
+    let target = base.join(rel_path);
+
+    // Path traversal guard.
+    let canonical = target
+        .canonicalize()
+        .map_err(|_| (StatusCode::NOT_FOUND, "Path not found".to_string()))?;
+    let base_canonical = base
+        .canonicalize()
+        .map_err(|_| (StatusCode::NOT_FOUND, "Project dir not found".to_string()))?;
+    if !canonical.starts_with(&base_canonical) {
+        return Err((StatusCode::FORBIDDEN, "Forbidden".to_string()));
+    }
+
+    let mut entries = Vec::new();
+    let mut read_dir = tokio::fs::read_dir(&canonical)
+        .await
+        .map_err(|_| (StatusCode::NOT_FOUND, "Cannot read directory".to_string()))?;
+
+    while let Ok(Some(entry)) = read_dir.next_entry().await {
+        let name = entry.file_name().to_string_lossy().to_string();
+        let is_dir = entry
+            .file_type()
+            .await
+            .map(|ft| ft.is_dir())
+            .unwrap_or(false);
+        let rel = if rel_path.is_empty() {
+            name.clone()
+        } else {
+            format!("{}/{}", rel_path, name)
+        };
+        entries.push(ProjectFileEntry {
+            name,
+            path: rel,
+            is_dir,
+        });
+    }
+
+    entries.sort_by(|a, b| b.is_dir.cmp(&a.is_dir).then_with(|| a.name.cmp(&b.name)));
+
+    Ok(Json(ProjectFilesResponse { entries }))
+}
+
+pub async fn job_files_read_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(id): Path<String>,
+    Query(query): Query<FilePathQuery>,
+) -> Result<Json<ProjectFileReadResponse>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let job_id = Uuid::parse_str(&id)
+        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid job ID".to_string()))?;
+
+    let job = store
+        .get_sandbox_job(job_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "Job not found".to_string()))?;
+
+    // Verify user owns this job.
+    if job.user_id != state.user_id {
+        return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+    }
+
+    let path = query.path.as_deref().ok_or((
+        StatusCode::BAD_REQUEST,
+        "path parameter required".to_string(),
+    ))?;
+
+    let base = std::path::PathBuf::from(&job.project_dir);
+    let file_path = base.join(path);
+
+    let canonical = file_path
+        .canonicalize()
+        .map_err(|_| (StatusCode::NOT_FOUND, "File not found".to_string()))?;
+    let base_canonical = base
+        .canonicalize()
+        .map_err(|_| (StatusCode::NOT_FOUND, "Project dir not found".to_string()))?;
+    if !canonical.starts_with(&base_canonical) {
+        return Err((StatusCode::FORBIDDEN, "Forbidden".to_string()));
+    }
+
+    let content = tokio::fs::read_to_string(&canonical)
+        .await
+        .map_err(|_| (StatusCode::NOT_FOUND, "Cannot read file".to_string()))?;
+
+    Ok(Json(ProjectFileReadResponse {
+        path: path.to_string(),
+        content,
+    }))
+}

src/channels/web/handlers/memory.rs

@@ -0,0 +1,171 @@
+//! Memory/workspace API handlers.
+
+use std::sync::Arc;
+
+use axum::{
+    Json,
+    extract::{Query, State},
+    http::StatusCode,
+};
+use serde::Deserialize;
+
+use crate::channels::web::server::GatewayState;
+use crate::channels::web::types::*;
+
+#[derive(Deserialize)]
+pub struct TreeQuery {
+    #[allow(dead_code)]
+    pub depth: Option<usize>,
+}
+
+pub async fn memory_tree_handler(
+    State(state): State<Arc<GatewayState>>,
+    Query(_query): Query<TreeQuery>,
+) -> Result<Json<MemoryTreeResponse>, (StatusCode, String)> {
+    let workspace = state.workspace.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Workspace not available".to_string(),
+    ))?;
+
+    // Build tree from list_all (flat list of all paths)
+    let all_paths = workspace
+        .list_all()
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    // Collect unique directories and files
+    let mut entries: Vec<TreeEntry> = Vec::new();
+    let mut seen_dirs: std::collections::HashSet<String> = std::collections::HashSet::new();
+
+    for path in &all_paths {
+        // Add parent directories
+        let parts: Vec<&str> = path.split('/').collect();
+        for i in 0..parts.len().saturating_sub(1) {
+            let dir_path = parts[..=i].join("/");
+            if seen_dirs.insert(dir_path.clone()) {
+                entries.push(TreeEntry {
+                    path: dir_path,
+                    is_dir: true,
+                });
+            }
+        }
+        // Add the file itself
+        entries.push(TreeEntry {
+            path: path.clone(),
+            is_dir: false,
+        });
+    }
+
+    entries.sort_by(|a, b| a.path.cmp(&b.path));
+
+    Ok(Json(MemoryTreeResponse { entries }))
+}
+
+#[derive(Deserialize)]
+pub struct ListQuery {
+    pub path: Option<String>,
+}
+
+pub async fn memory_list_handler(
+    State(state): State<Arc<GatewayState>>,
+    Query(query): Query<ListQuery>,
+) -> Result<Json<MemoryListResponse>, (StatusCode, String)> {
+    let workspace = state.workspace.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Workspace not available".to_string(),
+    ))?;
+
+    let path = query.path.as_deref().unwrap_or("");
+    let entries = workspace
+        .list(path)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    let list_entries: Vec<ListEntry> = entries
+        .iter()
+        .map(|e| ListEntry {
+            name: e.path.rsplit('/').next().unwrap_or(&e.path).to_string(),
+            path: e.path.clone(),
+            is_dir: e.is_directory,
+            updated_at: e.updated_at.map(|dt| dt.to_rfc3339()),
+        })
+        .collect();
+
+    Ok(Json(MemoryListResponse {
+        path: path.to_string(),
+        entries: list_entries,
+    }))
+}
+
+#[derive(Deserialize)]
+pub struct ReadQuery {
+    pub path: String,
+}
+
+pub async fn memory_read_handler(
+    State(state): State<Arc<GatewayState>>,
+    Query(query): Query<ReadQuery>,
+) -> Result<Json<MemoryReadResponse>, (StatusCode, String)> {
+    let workspace = state.workspace.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Workspace not available".to_string(),
+    ))?;
+
+    let doc = workspace
+        .read(&query.path)
+        .await
+        .map_err(|e| (StatusCode::NOT_FOUND, e.to_string()))?;
+
+    Ok(Json(MemoryReadResponse {
+        path: query.path,
+        content: doc.content,
+        updated_at: Some(doc.updated_at.to_rfc3339()),
+    }))
+}
+
+pub async fn memory_write_handler(
+    State(state): State<Arc<GatewayState>>,
+    Json(req): Json<MemoryWriteRequest>,
+) -> Result<Json<MemoryWriteResponse>, (StatusCode, String)> {
+    let workspace = state.workspace.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Workspace not available".to_string(),
+    ))?;
+
+    workspace
+        .write(&req.path, &req.content)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    Ok(Json(MemoryWriteResponse {
+        path: req.path,
+        status: "written",
+    }))
+}
+
+pub async fn memory_search_handler(
+    State(state): State<Arc<GatewayState>>,
+    Json(req): Json<MemorySearchRequest>,
+) -> Result<Json<MemorySearchResponse>, (StatusCode, String)> {
+    let workspace = state.workspace.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Workspace not available".to_string(),
+    ))?;
+
+    let limit = req.limit.unwrap_or(10);
+    let results = workspace
+        .search(&req.query, limit)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    let hits: Vec<SearchHit> = results
+        .iter()
+        .map(|r| SearchHit {
+            path: r.document_id.to_string(),
+            content: r.content.clone(),
+            score: r.score as f64,
+        })
+        .collect();
+
+    Ok(Json(MemorySearchResponse { results: hits }))
+}

src/channels/web/handlers/mod.rs

@@ -0,0 +1,23 @@
+//! Handler modules for the web gateway API.
+//!
+//! Each module groups related endpoint handlers by domain.
+
+pub mod chat;
+pub mod extensions;
+pub mod jobs;
+pub mod memory;
+pub mod routines;
+pub mod settings;
+pub mod skills;
+pub mod static_files;
+
+// Re-export all handler functions so `server.rs` can reference them
+// as `handlers::chat_send_handler`, etc.
+pub use chat::*;
+pub use extensions::*;
+pub use jobs::*;
+pub use memory::*;
+pub use routines::*;
+pub use settings::*;
+pub use skills::*;
+pub use static_files::*;

src/channels/web/handlers/routines.rs

@@ -0,0 +1,330 @@
+//! Routine management API handlers.
+
+use std::sync::Arc;
+
+use axum::{
+    Json,
+    extract::{Path, State},
+    http::StatusCode,
+};
+use serde::Deserialize;
+use uuid::Uuid;
+
+use crate::channels::IncomingMessage;
+use crate::channels::web::server::GatewayState;
+use crate::channels::web::types::*;
+
+pub async fn routines_list_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<Json<RoutineListResponse>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let routines = store
+        .list_routines(&state.user_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    let items: Vec<RoutineInfo> = routines.iter().map(routine_to_info).collect();
+
+    Ok(Json(RoutineListResponse { routines: items }))
+}
+
+pub async fn routines_summary_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<Json<RoutineSummaryResponse>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let routines = store
+        .list_routines(&state.user_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    let total = routines.len() as u64;
+    let enabled = routines.iter().filter(|r| r.enabled).count() as u64;
+    let disabled = total - enabled;
+    let failing = routines
+        .iter()
+        .filter(|r| r.consecutive_failures > 0)
+        .count() as u64;
+
+    let today_start = chrono::Utc::now()
+        .date_naive()
+        .and_hms_opt(0, 0, 0)
+        .map(|dt| dt.and_utc());
+    let runs_today = if let Some(start) = today_start {
+        routines
+            .iter()
+            .filter(|r| r.last_run_at.is_some_and(|ts| ts >= start))
+            .count() as u64
+    } else {
+        0
+    };
+
+    Ok(Json(RoutineSummaryResponse {
+        total,
+        enabled,
+        disabled,
+        failing,
+        runs_today,
+    }))
+}
+
+pub async fn routines_detail_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(id): Path<String>,
+) -> Result<Json<RoutineDetailResponse>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let routine_id = Uuid::parse_str(&id)
+        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid routine ID".to_string()))?;
+
+    let routine = store
+        .get_routine(routine_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "Routine not found".to_string()))?;
+
+    let runs = store
+        .list_routine_runs(routine_id, 20)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    let recent_runs: Vec<RoutineRunInfo> = runs
+        .iter()
+        .map(|run| RoutineRunInfo {
+            id: run.id,
+            trigger_type: run.trigger_type.clone(),
+            started_at: run.started_at.to_rfc3339(),
+            completed_at: run.completed_at.map(|dt| dt.to_rfc3339()),
+            status: format!("{:?}", run.status),
+            result_summary: run.result_summary.clone(),
+            tokens_used: run.tokens_used,
+        })
+        .collect();
+
+    Ok(Json(RoutineDetailResponse {
+        id: routine.id,
+        name: routine.name.clone(),
+        description: routine.description.clone(),
+        enabled: routine.enabled,
+        trigger: serde_json::to_value(&routine.trigger).unwrap_or_default(),
+        action: serde_json::to_value(&routine.action).unwrap_or_default(),
+        guardrails: serde_json::to_value(&routine.guardrails).unwrap_or_default(),
+        notify: serde_json::to_value(&routine.notify).unwrap_or_default(),
+        last_run_at: routine.last_run_at.map(|dt| dt.to_rfc3339()),
+        next_fire_at: routine.next_fire_at.map(|dt| dt.to_rfc3339()),
+        run_count: routine.run_count,
+        consecutive_failures: routine.consecutive_failures,
+        created_at: routine.created_at.to_rfc3339(),
+        recent_runs,
+    }))
+}
+
+pub async fn routines_trigger_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(id): Path<String>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let routine_id = Uuid::parse_str(&id)
+        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid routine ID".to_string()))?;
+
+    let routine = store
+        .get_routine(routine_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "Routine not found".to_string()))?;
+
+    // Send the routine prompt through the message pipeline as a manual trigger.
+    let prompt = match &routine.action {
+        crate::agent::routine::RoutineAction::Lightweight { prompt, .. } => prompt.clone(),
+        crate::agent::routine::RoutineAction::FullJob {
+            title, description, ..
+        } => format!("{}: {}", title, description),
+    };
+
+    let content = format!("[routine:{}] {}", routine.name, prompt);
+    let msg = IncomingMessage::new("gateway", &state.user_id, content);
+
+    let tx_guard = state.msg_tx.read().await;
+    let tx = tx_guard.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Channel not started".to_string(),
+    ))?;
+
+    tx.send(msg).await.map_err(|_| {
+        (
+            StatusCode::INTERNAL_SERVER_ERROR,
+            "Channel closed".to_string(),
+        )
+    })?;
+
+    Ok(Json(serde_json::json!({
+        "status": "triggered",
+        "routine_id": routine_id,
+    })))
+}
+
+#[derive(Deserialize)]
+pub struct ToggleRequest {
+    pub enabled: Option<bool>,
+}
+
+pub async fn routines_toggle_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(id): Path<String>,
+    body: Option<Json<ToggleRequest>>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let routine_id = Uuid::parse_str(&id)
+        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid routine ID".to_string()))?;
+
+    let mut routine = store
+        .get_routine(routine_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "Routine not found".to_string()))?;
+
+    // If a specific value was provided, use it; otherwise toggle.
+    routine.enabled = match body {
+        Some(Json(req)) => req.enabled.unwrap_or(!routine.enabled),
+        None => !routine.enabled,
+    };
+
+    store
+        .update_routine(&routine)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    Ok(Json(serde_json::json!({
+        "status": if routine.enabled { "enabled" } else { "disabled" },
+        "routine_id": routine_id,
+    })))
+}
+
+pub async fn routines_delete_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(id): Path<String>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let routine_id = Uuid::parse_str(&id)
+        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid routine ID".to_string()))?;
+
+    let deleted = store
+        .delete_routine(routine_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    if deleted {
+        Ok(Json(serde_json::json!({
+            "status": "deleted",
+            "routine_id": routine_id,
+        })))
+    } else {
+        Err((StatusCode::NOT_FOUND, "Routine not found".to_string()))
+    }
+}
+
+pub async fn routines_runs_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(id): Path<String>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let routine_id = Uuid::parse_str(&id)
+        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid routine ID".to_string()))?;
+
+    let runs = store
+        .list_routine_runs(routine_id, 50)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    let run_infos: Vec<RoutineRunInfo> = runs
+        .iter()
+        .map(|run| RoutineRunInfo {
+            id: run.id,
+            trigger_type: run.trigger_type.clone(),
+            started_at: run.started_at.to_rfc3339(),
+            completed_at: run.completed_at.map(|dt| dt.to_rfc3339()),
+            status: format!("{:?}", run.status),
+            result_summary: run.result_summary.clone(),
+            tokens_used: run.tokens_used,
+        })
+        .collect();
+
+    Ok(Json(serde_json::json!({
+        "routine_id": routine_id,
+        "runs": run_infos,
+    })))
+}
+
+/// Convert a Routine to the trimmed RoutineInfo for list display.
+fn routine_to_info(r: &crate::agent::routine::Routine) -> RoutineInfo {
+    let (trigger_type, trigger_summary) = match &r.trigger {
+        crate::agent::routine::Trigger::Cron { schedule } => {
+            ("cron".to_string(), format!("cron: {}", schedule))
+        }
+        crate::agent::routine::Trigger::Event {
+            pattern, channel, ..
+        } => {
+            let ch = channel.as_deref().unwrap_or("any");
+            ("event".to_string(), format!("on {} /{}/", ch, pattern))
+        }
+        crate::agent::routine::Trigger::Webhook { path, .. } => {
+            let p = path.as_deref().unwrap_or("/");
+            ("webhook".to_string(), format!("webhook: {}", p))
+        }
+        crate::agent::routine::Trigger::Manual => ("manual".to_string(), "manual only".to_string()),
+    };
+
+    let action_type = match &r.action {
+        crate::agent::routine::RoutineAction::Lightweight { .. } => "lightweight",
+        crate::agent::routine::RoutineAction::FullJob { .. } => "full_job",
+    };
+
+    let status = if !r.enabled {
+        "disabled"
+    } else if r.consecutive_failures > 0 {
+        "failing"
+    } else {
+        "active"
+    };
+
+    RoutineInfo {
+        id: r.id,
+        name: r.name.clone(),
+        description: r.description.clone(),
+        enabled: r.enabled,
+        trigger_type,
+        trigger_summary,
+        action_type: action_type.to_string(),
+        last_run_at: r.last_run_at.map(|dt| dt.to_rfc3339()),
+        next_fire_at: r.next_fire_at.map(|dt| dt.to_rfc3339()),
+        run_count: r.run_count,
+        consecutive_failures: r.consecutive_failures,
+        status: status.to_string(),
+    }
+}

src/channels/web/handlers/settings.rs

@@ -0,0 +1,133 @@
+//! Settings API handlers.
+
+use std::sync::Arc;
+
+use axum::{
+    Json,
+    extract::{Path, State},
+    http::StatusCode,
+};
+
+use crate::channels::web::server::GatewayState;
+use crate::channels::web::types::*;
+
+pub async fn settings_list_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<Json<SettingsListResponse>, StatusCode> {
+    let store = state
+        .store
+        .as_ref()
+        .ok_or(StatusCode::SERVICE_UNAVAILABLE)?;
+    let rows = store.list_settings(&state.user_id).await.map_err(|e| {
+        tracing::error!("Failed to list settings: {}", e);
+        StatusCode::INTERNAL_SERVER_ERROR
+    })?;
+
+    let settings = rows
+        .into_iter()
+        .map(|r| SettingResponse {
+            key: r.key,
+            value: r.value,
+            updated_at: r.updated_at.to_rfc3339(),
+        })
+        .collect();
+
+    Ok(Json(SettingsListResponse { settings }))
+}
+
+pub async fn settings_get_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(key): Path<String>,
+) -> Result<Json<SettingResponse>, StatusCode> {
+    let store = state
+        .store
+        .as_ref()
+        .ok_or(StatusCode::SERVICE_UNAVAILABLE)?;
+    let row = store
+        .get_setting_full(&state.user_id, &key)
+        .await
+        .map_err(|e| {
+            tracing::error!("Failed to get setting '{}': {}", key, e);
+            StatusCode::INTERNAL_SERVER_ERROR
+        })?
+        .ok_or(StatusCode::NOT_FOUND)?;
+
+    Ok(Json(SettingResponse {
+        key: row.key,
+        value: row.value,
+        updated_at: row.updated_at.to_rfc3339(),
+    }))
+}
+
+pub async fn settings_set_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(key): Path<String>,
+    Json(body): Json<SettingWriteRequest>,
+) -> Result<StatusCode, StatusCode> {
+    let store = state
+        .store
+        .as_ref()
+        .ok_or(StatusCode::SERVICE_UNAVAILABLE)?;
+    store
+        .set_setting(&state.user_id, &key, &body.value)
+        .await
+        .map_err(|e| {
+            tracing::error!("Failed to set setting '{}': {}", key, e);
+            StatusCode::INTERNAL_SERVER_ERROR
+        })?;
+
+    Ok(StatusCode::NO_CONTENT)
+}
+
+pub async fn settings_delete_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path(key): Path<String>,
+) -> Result<StatusCode, StatusCode> {
+    let store = state
+        .store
+        .as_ref()
+        .ok_or(StatusCode::SERVICE_UNAVAILABLE)?;
+    store
+        .delete_setting(&state.user_id, &key)
+        .await
+        .map_err(|e| {
+            tracing::error!("Failed to delete setting '{}': {}", key, e);
+            StatusCode::INTERNAL_SERVER_ERROR
+        })?;
+
+    Ok(StatusCode::NO_CONTENT)
+}
+
+pub async fn settings_export_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<Json<SettingsExportResponse>, StatusCode> {
+    let store = state
+        .store
+        .as_ref()
+        .ok_or(StatusCode::SERVICE_UNAVAILABLE)?;
+    let settings = store.get_all_settings(&state.user_id).await.map_err(|e| {
+        tracing::error!("Failed to export settings: {}", e);
+        StatusCode::INTERNAL_SERVER_ERROR
+    })?;
+
+    Ok(Json(SettingsExportResponse { settings }))
+}
+
+pub async fn settings_import_handler(
+    State(state): State<Arc<GatewayState>>,
+    Json(body): Json<SettingsImportRequest>,
+) -> Result<StatusCode, StatusCode> {
+    let store = state
+        .store
+        .as_ref()
+        .ok_or(StatusCode::SERVICE_UNAVAILABLE)?;
+    store
+        .set_all_settings(&state.user_id, &body.settings)
+        .await
+        .map_err(|e| {
+            tracing::error!("Failed to import settings: {}", e);
+            StatusCode::INTERNAL_SERVER_ERROR
+        })?;
+
+    Ok(StatusCode::NO_CONTENT)
+}

src/channels/web/handlers/skills.rs

@@ -0,0 +1,257 @@
+//! Skills management API handlers.
+
+use std::sync::Arc;
+
+use axum::{
+    Json,
+    extract::{Path, State},
+    http::StatusCode,
+};
+
+use crate::channels::web::server::GatewayState;
+use crate::channels::web::types::*;
+
+pub async fn skills_list_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<Json<SkillListResponse>, (StatusCode, String)> {
+    let registry = state.skill_registry.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Skills system not enabled".to_string(),
+    ))?;
+
+    let guard = registry.read().map_err(|e| {
+        (
+            StatusCode::INTERNAL_SERVER_ERROR,
+            format!("Skill registry lock poisoned: {}", e),
+        )
+    })?;
+
+    let skills: Vec<SkillInfo> = guard
+        .skills()
+        .iter()
+        .map(|s| SkillInfo {
+            name: s.manifest.name.clone(),
+            description: s.manifest.description.clone(),
+            version: s.manifest.version.clone(),
+            trust: s.trust.to_string(),
+            source: format!("{:?}", s.source),
+            keywords: s.manifest.activation.keywords.clone(),
+        })
+        .collect();
+
+    let count = skills.len();
+    Ok(Json(SkillListResponse { skills, count }))
+}
+
+pub async fn skills_search_handler(
+    State(state): State<Arc<GatewayState>>,
+    Json(req): Json<SkillSearchRequest>,
+) -> Result<Json<SkillSearchResponse>, (StatusCode, String)> {
+    let registry = state.skill_registry.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Skills system not enabled".to_string(),
+    ))?;
+
+    let catalog = state.skill_catalog.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Skill catalog not available".to_string(),
+    ))?;
+
+    // Search ClawHub catalog
+    let catalog_results = catalog.search(&req.query).await;
+    let catalog_json: Vec<serde_json::Value> = catalog_results
+        .into_iter()
+        .map(|e| {
+            serde_json::json!({
+                "slug": e.slug,
+                "name": e.name,
+                "description": e.description,
+                "version": e.version,
+                "score": e.score,
+            })
+        })
+        .collect();
+
+    // Search local skills
+    let query_lower = req.query.to_lowercase();
+    let installed: Vec<SkillInfo> = {
+        let guard = registry.read().map_err(|e| {
+            (
+                StatusCode::INTERNAL_SERVER_ERROR,
+                format!("Skill registry lock poisoned: {}", e),
+            )
+        })?;
+        guard
+            .skills()
+            .iter()
+            .filter(|s| {
+                s.manifest.name.to_lowercase().contains(&query_lower)
+                    || s.manifest.description.to_lowercase().contains(&query_lower)
+            })
+            .map(|s| SkillInfo {
+                name: s.manifest.name.clone(),
+                description: s.manifest.description.clone(),
+                version: s.manifest.version.clone(),
+                trust: s.trust.to_string(),
+                source: format!("{:?}", s.source),
+                keywords: s.manifest.activation.keywords.clone(),
+            })
+            .collect()
+    };
+
+    Ok(Json(SkillSearchResponse {
+        catalog: catalog_json,
+        installed,
+        registry_url: catalog.registry_url().to_string(),
+    }))
+}
+
+pub async fn skills_install_handler(
+    State(state): State<Arc<GatewayState>>,
+    headers: axum::http::HeaderMap,
+    Json(req): Json<SkillInstallRequest>,
+) -> Result<Json<ActionResponse>, (StatusCode, String)> {
+    // Require explicit confirmation header to prevent accidental installs.
+    // Chat tools have requires_approval(); this is the equivalent for the web API.
+    if headers
+        .get("x-confirm-action")
+        .and_then(|v| v.to_str().ok())
+        != Some("true")
+    {
+        return Err((
+            StatusCode::BAD_REQUEST,
+            "Skill install requires X-Confirm-Action: true header".to_string(),
+        ));
+    }
+
+    let registry = state.skill_registry.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Skills system not enabled".to_string(),
+    ))?;
+
+    let content = if let Some(ref raw) = req.content {
+        raw.clone()
+    } else if let Some(ref url) = req.url {
+        // Fetch from explicit URL (with SSRF protection)
+        crate::tools::builtin::skill_tools::fetch_skill_content(url)
+            .await
+            .map_err(|e| (StatusCode::BAD_REQUEST, e.to_string()))?
+    } else if let Some(ref catalog) = state.skill_catalog {
+        let url = crate::skills::catalog::skill_download_url(catalog.registry_url(), &req.name);
+        crate::tools::builtin::skill_tools::fetch_skill_content(&url)
+            .await
+            .map_err(|e| (StatusCode::BAD_GATEWAY, e.to_string()))?
+    } else {
+        return Ok(Json(ActionResponse::fail(
+            "Provide 'content' or 'url' to install a skill".to_string(),
+        )));
+    };
+
+    // Parse, check duplicates, and get user_dir under a brief read lock.
+    let (user_dir, skill_name_from_parse) = {
+        let guard = registry.read().map_err(|e| {
+            (
+                StatusCode::INTERNAL_SERVER_ERROR,
+                format!("Skill registry lock poisoned: {}", e),
+            )
+        })?;
+
+        let normalized = crate::skills::normalize_line_endings(&content);
+        let parsed = crate::skills::parser::parse_skill_md(&normalized)
+            .map_err(|e| (StatusCode::BAD_REQUEST, e.to_string()))?;
+        let skill_name = parsed.manifest.name.clone();
+
+        if guard.has(&skill_name) {
+            return Ok(Json(ActionResponse::fail(format!(
+                "Skill '{}' already exists",
+                skill_name
+            ))));
+        }
+
+        (guard.user_dir().to_path_buf(), skill_name)
+    };
+
+    // Perform async I/O (write to disk, load) with no lock held.
+    let normalized = crate::skills::normalize_line_endings(&content);
+    let (skill_name, loaded_skill) =
+        crate::skills::registry::SkillRegistry::prepare_install_to_disk(
+            &user_dir,
+            &skill_name_from_parse,
+            &normalized,
+        )
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    // Commit: brief write lock for in-memory addition
+    let mut guard = registry.write().map_err(|e| {
+        (
+            StatusCode::INTERNAL_SERVER_ERROR,
+            format!("Skill registry lock poisoned: {}", e),
+        )
+    })?;
+
+    match guard.commit_install(&skill_name, loaded_skill) {
+        Ok(()) => Ok(Json(ActionResponse::ok(format!(
+            "Skill '{}' installed",
+            skill_name
+        )))),
+        Err(e) => Ok(Json(ActionResponse::fail(e.to_string()))),
+    }
+}
+
+pub async fn skills_remove_handler(
+    State(state): State<Arc<GatewayState>>,
+    headers: axum::http::HeaderMap,
+    Path(name): Path<String>,
+) -> Result<Json<ActionResponse>, (StatusCode, String)> {
+    // Require explicit confirmation header to prevent accidental removals.
+    if headers
+        .get("x-confirm-action")
+        .and_then(|v| v.to_str().ok())
+        != Some("true")
+    {
+        return Err((
+            StatusCode::BAD_REQUEST,
+            "Skill removal requires X-Confirm-Action: true header".to_string(),
+        ));
+    }
+
+    let registry = state.skill_registry.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Skills system not enabled".to_string(),
+    ))?;
+
+    // Validate removal under a brief read lock
+    let skill_path = {
+        let guard = registry.read().map_err(|e| {
+            (
+                StatusCode::INTERNAL_SERVER_ERROR,
+                format!("Skill registry lock poisoned: {}", e),
+            )
+        })?;
+        guard
+            .validate_remove(&name)
+            .map_err(|e| (StatusCode::BAD_REQUEST, e.to_string()))?
+    };
+
+    // Delete files from disk (async I/O, no lock held)
+    crate::skills::registry::SkillRegistry::delete_skill_files(&skill_path)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    // Remove from in-memory registry under a brief write lock
+    let mut guard = registry.write().map_err(|e| {
+        (
+            StatusCode::INTERNAL_SERVER_ERROR,
+            format!("Skill registry lock poisoned: {}", e),
+        )
+    })?;
+
+    match guard.commit_remove(&name) {
+        Ok(()) => Ok(Json(ActionResponse::ok(format!(
+            "Skill '{}' removed",
+            name
+        )))),
+        Err(e) => Ok(Json(ActionResponse::fail(e.to_string()))),
+    }
+}

src/channels/web/handlers/static_files.rs

@@ -0,0 +1,178 @@
+//! Static file and health handlers.
+
+use axum::{
+    Json,
+    http::{StatusCode, header},
+    response::{Html, IntoResponse},
+};
+
+use crate::channels::web::types::*;
+
+// --- Static file handlers ---
+
+pub async fn index_handler() -> Html<&'static str> {
+    Html(include_str!("../static/index.html"))
+}
+
+pub async fn css_handler() -> impl IntoResponse {
+    (
+        [(header::CONTENT_TYPE, "text/css")],
+        include_str!("../static/style.css"),
+    )
+}
+
+pub async fn js_handler() -> impl IntoResponse {
+    (
+        [(header::CONTENT_TYPE, "application/javascript")],
+        include_str!("../static/app.js"),
+    )
+}
+
+// --- Health ---
+
+pub async fn health_handler() -> Json<HealthResponse> {
+    Json(HealthResponse {
+        status: "healthy",
+        channel: "gateway",
+    })
+}
+
+// --- Project file serving handlers ---
+
+use axum::extract::Path;
+
+/// Redirect `/projects/{id}` to `/projects/{id}/` so relative paths in
+/// the served HTML resolve within the project namespace.
+pub async fn project_redirect_handler(Path(project_id): Path<String>) -> impl IntoResponse {
+    axum::response::Redirect::permanent(&format!("/projects/{project_id}/"))
+}
+
+/// Serve `index.html` when hitting `/projects/{project_id}/`.
+pub async fn project_index_handler(Path(project_id): Path<String>) -> impl IntoResponse {
+    serve_project_file(&project_id, "index.html").await
+}
+
+/// Serve any file under `/projects/{project_id}/{path}`.
+pub async fn project_file_handler(
+    Path((project_id, path)): Path<(String, String)>,
+) -> impl IntoResponse {
+    serve_project_file(&project_id, &path).await
+}
+
+/// Shared logic: resolve the file inside `~/.ironclaw/projects/{project_id}/`,
+/// guard against path traversal, and stream the content with the right MIME type.
+async fn serve_project_file(project_id: &str, path: &str) -> axum::response::Response {
+    // Reject project_id values that could escape the projects directory.
+    if project_id.contains('/')
+        || project_id.contains('\\')
+        || project_id.contains("..")
+        || project_id.is_empty()
+    {
+        return (StatusCode::BAD_REQUEST, "Invalid project ID").into_response();
+    }
+
+    let base = dirs::home_dir()
+        .unwrap_or_else(|| std::path::PathBuf::from("."))
+        .join(".ironclaw")
+        .join("projects")
+        .join(project_id);
+
+    let file_path = base.join(path);
+
+    // Path traversal guard
+    let canonical = match file_path.canonicalize() {
+        Ok(p) => p,
+        Err(_) => return (StatusCode::NOT_FOUND, "Not found").into_response(),
+    };
+    let base_canonical = match base.canonicalize() {
+        Ok(p) => p,
+        Err(_) => return (StatusCode::NOT_FOUND, "Not found").into_response(),
+    };
+    if !canonical.starts_with(&base_canonical) {
+        return (StatusCode::FORBIDDEN, "Forbidden").into_response();
+    }
+
+    match tokio::fs::read(&canonical).await {
+        Ok(contents) => {
+            let mime = mime_guess::from_path(&canonical)
+                .first_or_octet_stream()
+                .to_string();
+            ([(header::CONTENT_TYPE, mime)], contents).into_response()
+        }
+        Err(_) => (StatusCode::NOT_FOUND, "Not found").into_response(),
+    }
+}
+
+// --- Logs ---
+
+use std::convert::Infallible;
+use std::sync::Arc;
+
+use axum::extract::State;
+use axum::response::sse::{Event, KeepAlive, Sse};
+use tokio_stream::StreamExt;
+
+use crate::channels::web::server::GatewayState;
+
+pub async fn logs_events_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<
+    Sse<impl futures::Stream<Item = Result<Event, Infallible>> + Send + 'static>,
+    (StatusCode, String),
+> {
+    let broadcaster = state.log_broadcaster.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Log broadcaster not available".to_string(),
+    ))?;
+
+    // Replay recent history so late-joining browsers see startup logs.
+    // Subscribe BEFORE snapshotting to avoid a gap between history and live.
+    let rx = broadcaster.subscribe();
+    let history = broadcaster.recent_entries();
+
+    let history_stream = futures::stream::iter(history).map(|entry| {
+        let data = serde_json::to_string(&entry).unwrap_or_default();
+        Ok(Event::default().event("log").data(data))
+    });
+
+    let live_stream = tokio_stream::wrappers::BroadcastStream::new(rx)
+        .filter_map(|result| result.ok())
+        .map(|entry| {
+            let data = serde_json::to_string(&entry).unwrap_or_default();
+            Ok(Event::default().event("log").data(data))
+        });
+
+    let stream = history_stream.chain(live_stream);
+
+    Ok(Sse::new(stream).keep_alive(
+        KeepAlive::new()
+            .interval(std::time::Duration::from_secs(30))
+            .text(""),
+    ))
+}
+
+// --- Gateway status ---
+
+pub async fn gateway_status_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Json<GatewayStatusResponse> {
+    let sse_connections = state.sse.connection_count();
+    let ws_connections = state
+        .ws_tracker
+        .as_ref()
+        .map(|t| t.connection_count())
+        .unwrap_or(0);
+
+    Json(GatewayStatusResponse {
+        sse_connections,
+        ws_connections,
+        total_connections: sse_connections + ws_connections,
+    })
+}
+
+#[derive(serde::Serialize)]
+pub struct GatewayStatusResponse {
+    pub sse_connections: u64,
+    pub ws_connections: u64,
+    pub total_connections: u64,
+}

src/channels/web/log_layer.rs

@@ -22,7 +22,9 @@ use std::sync::{Arc, Mutex};
 use serde::Serialize;
 use tokio::sync::broadcast;
 use tracing::field::{Field, Visit};
-use tracing_subscriber::Layer;
+use tracing_subscriber::layer::SubscriberExt;
+use tracing_subscriber::util::SubscriberInitExt;
+use tracing_subscriber::{EnvFilter, Layer, reload};
 
 use crate::safety::LeakDetector;
 
@@ -102,6 +104,115 @@ impl Default for LogBroadcaster {
     }
 }
 
+/// Handle for changing the tracing `EnvFilter` at runtime.
+///
+/// Wraps a `reload::Handle` so the gateway can switch between log levels
+/// (e.g. `ironclaw=debug`) without restarting the process.
+pub struct LogLevelHandle {
+    handle: reload::Handle<EnvFilter, tracing_subscriber::Registry>,
+    current_level: Mutex<String>,
+    base_filter: String,
+}
+
+impl LogLevelHandle {
+    pub fn new(
+        handle: reload::Handle<EnvFilter, tracing_subscriber::Registry>,
+        initial_level: String,
+        base_filter: String,
+    ) -> Self {
+        Self {
+            handle,
+            current_level: Mutex::new(initial_level),
+            base_filter,
+        }
+    }
+
+    /// Change the `ironclaw=<level>` directive at runtime.
+    ///
+    /// `level` must be one of: trace, debug, info, warn, error.
+    pub fn set_level(&self, level: &str) -> Result<(), String> {
+        const VALID: &[&str] = &["trace", "debug", "info", "warn", "error"];
+        let level = level.to_lowercase();
+        if !VALID.contains(&level.as_str()) {
+            return Err(format!(
+                "invalid level '{}', must be one of: {}",
+                level,
+                VALID.join(", ")
+            ));
+        }
+
+        let filter_str = if self.base_filter.is_empty() {
+            format!("ironclaw={}", level)
+        } else {
+            format!("ironclaw={},{}", level, self.base_filter)
+        };
+
+        let new_filter = EnvFilter::new(&filter_str);
+        self.handle
+            .reload(new_filter)
+            .map_err(|e| format!("failed to reload filter: {}", e))?;
+
+        if let Ok(mut current) = self.current_level.lock() {
+            *current = level;
+        }
+        Ok(())
+    }
+
+    /// Returns the current ironclaw log level (e.g. "info", "debug").
+    pub fn current_level(&self) -> String {
+        self.current_level
+            .lock()
+            .map(|l| l.clone())
+            .unwrap_or_else(|_| "info".to_string())
+    }
+}
+
+/// Initialise the tracing subscriber with a reloadable `EnvFilter`.
+///
+/// Returns the `LogLevelHandle` so callers can swap the filter at runtime.
+/// The fmt layer and `WebLogLayer` are attached alongside the reloadable filter.
+pub fn init_tracing(log_broadcaster: Arc<LogBroadcaster>) -> Arc<LogLevelHandle> {
+    let raw_filter =
+        std::env::var("RUST_LOG").unwrap_or_else(|_| "ironclaw=info,tower_http=warn".to_string());
+
+    // Split into the ironclaw directive and "everything else" (base_filter).
+    let mut ironclaw_level = String::from("info");
+    let mut base_parts: Vec<&str> = Vec::new();
+
+    for part in raw_filter.split(',') {
+        let trimmed = part.trim();
+        if trimmed.starts_with("ironclaw=") {
+            if let Some(lvl) = trimmed.strip_prefix("ironclaw=") {
+                ironclaw_level = lvl.to_string();
+            }
+        } else if !trimmed.is_empty() {
+            base_parts.push(trimmed);
+        }
+    }
+    let base_filter = base_parts.join(",");
+
+    let env_filter = EnvFilter::new(&raw_filter);
+    let (reload_layer, reload_handle) = reload::Layer::new(env_filter);
+
+    let handle = Arc::new(LogLevelHandle::new(
+        reload_handle,
+        ironclaw_level,
+        base_filter,
+    ));
+
+    tracing_subscriber::registry()
+        .with(reload_layer)
+        .with(
+            tracing_subscriber::fmt::layer()
+                .with_target(false)
+                .with_writer(crate::tracing_fmt::TruncatingStderr::default()),
+        )
+        .with(WebLogLayer::new(log_broadcaster))
+        .init();
+
+    handle
+}
+
 /// Visitor that extracts the `message` field and all extra key-value
 /// fields from a tracing event.
 ///

src/channels/web/mod.rs

@@ -36,10 +36,12 @@ use crate::db::Database;
 use crate::error::ChannelError;
 use crate::extensions::ExtensionManager;
 use crate::orchestrator::job_manager::ContainerJobManager;
+use crate::skills::catalog::SkillCatalog;
+use crate::skills::registry::SkillRegistry;
 use crate::tools::ToolRegistry;
 use crate::workspace::Workspace;
 
-use self::log_layer::LogBroadcaster;
+use self::log_layer::{LogBroadcaster, LogLevelHandle};
 
 use self::server::GatewayState;
 use self::sse::SseManager;
@@ -74,6 +76,7 @@ impl GatewayChannel {
             workspace: None,
             session_manager: None,
             log_broadcaster: None,
+            log_level_handle: None,
             extension_manager: None,
             tool_registry: None,
             store: None,
@@ -83,6 +86,8 @@ impl GatewayChannel {
             shutdown_tx: tokio::sync::RwLock::new(None),
             ws_tracker: Some(Arc::new(ws::WsConnectionTracker::new())),
             llm_provider: None,
+            skill_registry: None,
+            skill_catalog: None,
             chat_rate_limiter: server::RateLimiter::new(30, 60),
         });
 
@@ -101,6 +106,7 @@ impl GatewayChannel {
             workspace: self.state.workspace.clone(),
             session_manager: self.state.session_manager.clone(),
             log_broadcaster: self.state.log_broadcaster.clone(),
+            log_level_handle: self.state.log_level_handle.clone(),
             extension_manager: self.state.extension_manager.clone(),
             tool_registry: self.state.tool_registry.clone(),
             store: self.state.store.clone(),
@@ -110,6 +116,8 @@ impl GatewayChannel {
             shutdown_tx: tokio::sync::RwLock::new(None),
             ws_tracker: self.state.ws_tracker.clone(),
             llm_provider: self.state.llm_provider.clone(),
+            skill_registry: self.state.skill_registry.clone(),
+            skill_catalog: self.state.skill_catalog.clone(),
             chat_rate_limiter: server::RateLimiter::new(30, 60),
         };
         mutate(&mut new_state);
@@ -134,6 +142,12 @@ impl GatewayChannel {
         self
     }
 
+    /// Inject the log level handle for runtime log level control.
+    pub fn with_log_level_handle(mut self, h: Arc<LogLevelHandle>) -> Self {
+        self.rebuild_state(|s| s.log_level_handle = Some(h));
+        self
+    }
+
     /// Inject the extension manager for the extensions API.
     pub fn with_extension_manager(mut self, em: Arc<ExtensionManager>) -> Self {
         self.rebuild_state(|s| s.extension_manager = Some(em));
@@ -174,6 +188,18 @@ impl GatewayChannel {
         self
     }
 
+    /// Inject the skill registry for skill management API.
+    pub fn with_skill_registry(mut self, sr: Arc<std::sync::RwLock<SkillRegistry>>) -> Self {
+        self.rebuild_state(|s| s.skill_registry = Some(sr));
+        self
+    }
+
+    /// Inject the skill catalog for skill search API.
+    pub fn with_skill_catalog(mut self, sc: Arc<SkillCatalog>) -> Self {
+        self.rebuild_state(|s| s.skill_catalog = Some(sc));
+        self
+    }
+
     /// Inject the LLM provider for OpenAI-compatible API proxy.
     pub fn with_llm_provider(mut self, llm: Arc<dyn crate::llm::LlmProvider>) -> Self {
         self.rebuild_state(|s| s.llm_provider = Some(llm));
@@ -287,6 +313,7 @@ impl Channel for GatewayChannel {
                 description,
                 parameters: serde_json::to_string_pretty(&parameters)
                     .unwrap_or_else(|_| parameters.to_string()),
+                thread_id,
             },
             StatusUpdate::AuthRequired {
                 extension_name,

src/channels/web/openai_compat.rs

@@ -24,6 +24,8 @@ use crate::llm::{
 
 use super::server::GatewayState;
 
+const MAX_MODEL_NAME_BYTES: usize = 256;
+
 // ---------------------------------------------------------------------------
 // OpenAI request types
 // ---------------------------------------------------------------------------
@@ -380,6 +382,27 @@ fn unix_timestamp() -> u64 {
         .as_secs()
 }
 
+fn validate_model_name(model: &str) -> Result<(), String> {
+    let trimmed = model.trim();
+
+    if trimmed.is_empty() {
+        return Err("model must not be empty".to_string());
+    }
+    if trimmed != model {
+        return Err("model must not have leading or trailing whitespace".to_string());
+    }
+    if model.len() > MAX_MODEL_NAME_BYTES {
+        return Err(format!(
+            "model must be at most {} bytes",
+            MAX_MODEL_NAME_BYTES
+        ));
+    }
+    if model.chars().any(char::is_control) {
+        return Err("model contains control characters".to_string());
+    }
+    Ok(())
+}
+
 /// Extract stop sequences from the flexible `stop` field.
 fn parse_stop(val: &serde_json::Value) -> Option<Vec<String>> {
     match val {
@@ -426,29 +449,17 @@ pub async fn chat_completions_handler(
             "invalid_request_error",
         ));
     }
-
-    // Validate the requested model matches the active model.
-    // Per-request model switching is not yet supported (see GH issue).
-    let active_model = llm.active_model_name();
-    if req.model != active_model {
-        return Err((
-            StatusCode::NOT_FOUND,
-            Json(OpenAiErrorResponse {
-                error: OpenAiErrorDetail {
-                    message: format!(
-                        "Model '{}' not found. The active model is '{}'.",
-                        req.model, active_model
-                    ),
-                    error_type: "invalid_request_error".to_string(),
-                    param: Some("model".to_string()),
-                    code: Some("model_not_found".to_string()),
-                },
-            }),
+    if let Err(e) = validate_model_name(&req.model) {
+        return Err(openai_error(
+            StatusCode::BAD_REQUEST,
+            e,
+            "invalid_request_error",
         ));
     }
 
     let has_tools = req.tools.as_ref().is_some_and(|t| !t.is_empty());
     let stream = req.stream.unwrap_or(false);
+    let requested_model = req.model.clone();
 
     if stream {
         return handle_streaming(llm.clone(), req, has_tools)
@@ -460,13 +471,12 @@ pub async fn chat_completions_handler(
 
     let messages = convert_messages(&req.messages)
         .map_err(|e| openai_error(StatusCode::BAD_REQUEST, e, "invalid_request_error"))?;
-    let model_name = llm.active_model_name();
     let id = chat_completion_id();
     let created = unix_timestamp();
 
     if has_tools {
         let tools = convert_tools(req.tools.as_deref().unwrap_or(&[]));
-        let mut tool_req = ToolCompletionRequest::new(messages, tools);
+        let mut tool_req = ToolCompletionRequest::new(messages, tools).with_model(req.model);
         if let Some(t) = req.temperature {
             tool_req = tool_req.with_temperature(t);
         }
@@ -483,6 +493,7 @@ pub async fn chat_completions_handler(
             .complete_with_tools(tool_req)
             .await
             .map_err(map_llm_error)?;
+        let model_name = llm.effective_model_name(Some(requested_model.as_str()));
 
         let tool_calls_openai = if resp.tool_calls.is_empty() {
             None
@@ -515,7 +526,7 @@ pub async fn chat_completions_handler(
 
         Ok(Json(response).into_response())
     } else {
-        let mut comp_req = CompletionRequest::new(messages);
+        let mut comp_req = CompletionRequest::new(messages).with_model(req.model);
         if let Some(t) = req.temperature {
             comp_req = comp_req.with_temperature(t);
         }
@@ -527,6 +538,7 @@ pub async fn chat_completions_handler(
         }
 
         let resp = llm.complete(comp_req).await.map_err(map_llm_error)?;
+        let model_name = llm.effective_model_name(Some(requested_model.as_str()));
 
         let response = OpenAiChatResponse {
             id,
@@ -570,7 +582,7 @@ async fn handle_streaming(
     let messages = convert_messages(&req.messages)
         .map_err(|e| openai_error(StatusCode::BAD_REQUEST, e, "invalid_request_error"))?;
 
-    let model_name = llm.active_model_name();
+    let requested_model = req.model.clone();
     let id = chat_completion_id();
     let created = unix_timestamp();
 
@@ -584,7 +596,7 @@ async fn handle_streaming(
 
     let llm_result = if has_tools {
         let tools = convert_tools(req.tools.as_deref().unwrap_or(&[]));
-        let mut tool_req = ToolCompletionRequest::new(messages, tools);
+        let mut tool_req = ToolCompletionRequest::new(messages, tools).with_model(req.model);
         if let Some(t) = req.temperature {
             tool_req = tool_req.with_temperature(t);
         }
@@ -602,7 +614,7 @@ async fn handle_streaming(
                 .map_err(map_llm_error)?,
         )
     } else {
-        let mut comp_req = CompletionRequest::new(messages);
+        let mut comp_req = CompletionRequest::new(messages).with_model(req.model);
         if let Some(t) = req.temperature {
             comp_req = comp_req.with_temperature(t);
         }
@@ -614,6 +626,7 @@ async fn handle_streaming(
         }
         LlmResult::Simple(llm.complete(comp_req).await.map_err(map_llm_error)?)
     };
+    let model_name = llm.effective_model_name(Some(requested_model.as_str()));
 
     // LLM succeeded — emit the response as SSE chunks
     let (tx, rx) = tokio::sync::mpsc::channel::<Result<Event, std::convert::Infallible>>(64);
@@ -1091,4 +1104,18 @@ mod tests {
         let v = serde_json::Value::Null;
         assert_eq!(parse_stop(&v), None);
     }
+
+    #[test]
+    fn test_validate_model_name_rejects_leading_or_trailing_whitespace() {
+        let err = validate_model_name(" gpt-4").unwrap_err();
+        assert!(err.contains("leading or trailing whitespace"));
+
+        let err = validate_model_name("gpt-4 ").unwrap_err();
+        assert!(err.contains("leading or trailing whitespace"));
+    }
+
+    #[test]
+    fn test_validate_model_name_accepts_normal_name() {
+        assert!(validate_model_name("gpt-4").is_ok());
+    }
 }

src/channels/web/server.rs

@@ -22,6 +22,7 @@ use serde::Deserialize;
 use tokio::sync::{mpsc, oneshot};
 use tokio_stream::StreamExt;
 use tower_http::cors::{AllowHeaders, CorsLayer};
+use tower_http::set_header::SetResponseHeaderLayer;
 use uuid::Uuid;
 
 use crate::agent::SessionManager;
@@ -121,6 +122,8 @@ pub struct GatewayState {
     pub session_manager: Option<Arc<SessionManager>>,
     /// Log broadcaster for the logs SSE endpoint.
     pub log_broadcaster: Option<Arc<LogBroadcaster>>,
+    /// Handle for changing the tracing log level at runtime.
+    pub log_level_handle: Option<Arc<crate::channels::web::log_layer::LogLevelHandle>>,
     /// Extension manager for extension management API.
     pub extension_manager: Option<Arc<ExtensionManager>>,
     /// Tool registry for listing registered tools.
@@ -139,6 +142,10 @@ pub struct GatewayState {
     pub ws_tracker: Option<Arc<crate::channels::web::ws::WsConnectionTracker>>,
     /// LLM provider for OpenAI-compatible API proxy.
     pub llm_provider: Option<Arc<dyn crate::llm::LlmProvider>>,
+    /// Skill registry for skill management API.
+    pub skill_registry: Option<Arc<std::sync::RwLock<crate::skills::SkillRegistry>>>,
+    /// Skill catalog for searching the ClawHub registry.
+    pub skill_catalog: Option<Arc<crate::skills::catalog::SkillCatalog>>,
     /// Rate limiter for chat endpoints (30 messages per 60 seconds).
     pub chat_rate_limiter: RateLimiter,
 }
@@ -199,6 +206,11 @@ pub async fn start_server(
         .route("/api/jobs/{id}/files/read", get(job_files_read_handler))
         // Logs
         .route("/api/logs/events", get(logs_events_handler))
+        .route("/api/logs/level", get(logs_level_get_handler))
+        .route(
+            "/api/logs/level",
+            axum::routing::put(logs_level_set_handler),
+        )
         // Extensions
         .route("/api/extensions", get(extensions_list_handler))
         .route("/api/extensions/tools", get(extensions_tools_handler))
@@ -222,6 +234,14 @@ pub async fn start_server(
             axum::routing::delete(routines_delete_handler),
         )
         .route("/api/routines/{id}/runs", get(routines_runs_handler))
+        // Skills
+        .route("/api/skills", get(skills_list_handler))
+        .route("/api/skills/search", post(skills_search_handler))
+        .route("/api/skills/install", post(skills_install_handler))
+        .route(
+            "/api/skills/{name}",
+            axum::routing::delete(skills_remove_handler),
+        )
         // Settings
         .route("/api/settings", get(settings_list_handler))
         .route("/api/settings/export", get(settings_export_handler))
@@ -292,8 +312,16 @@ pub async fn start_server(
         .merge(statics)
         .merge(projects)
         .merge(protected)
-        .layer(cors)
         .layer(DefaultBodyLimit::max(1024 * 1024)) // 1 MB max request body
+        .layer(cors)
+        .layer(SetResponseHeaderLayer::if_not_present(
+            header::X_CONTENT_TYPE_OPTIONS,
+            header::HeaderValue::from_static("nosniff"),
+        ))
+        .layer(SetResponseHeaderLayer::if_not_present(
+            header::X_FRAME_OPTIONS,
+            header::HeaderValue::from_static("DENY"),
+        ))
         .with_state(state.clone());
 
     let (shutdown_tx, shutdown_rx) = oneshot::channel();
@@ -536,9 +564,13 @@ pub async fn clear_auth_mode(state: &GatewayState) {
 async fn chat_events_handler(
     State(state): State<Arc<GatewayState>>,
 ) -> Result<impl IntoResponse, (StatusCode, String)> {
-    state.sse.subscribe().ok_or((
+    let sse = state.sse.subscribe().ok_or((
         StatusCode::SERVICE_UNAVAILABLE,
         "Too many connections".to_string(),
+    ))?;
+    Ok((
+        [("X-Accel-Buffering", "no"), ("Cache-Control", "no-cache")],
+        sse,
     ))
 }
 
@@ -1281,6 +1313,7 @@ async fn jobs_restart_handler(
         created_at: now,
         started_at: None,
         completed_at: None,
+        credential_grants_json: old_job.credential_grants_json.clone(),
     };
     store
         .save_sandbox_job(&record)
@@ -1293,9 +1326,28 @@ async fn jobs_restart_handler(
         _ => crate::orchestrator::job_manager::JobMode::Worker,
     };
 
+    // Restore credential grants from the original job so the restarted container
+    // has access to the same secrets.
+    let credential_grants: Vec<crate::orchestrator::auth::CredentialGrant> =
+        serde_json::from_str(&old_job.credential_grants_json).unwrap_or_else(|e| {
+            tracing::warn!(
+                job_id = %old_job.id,
+                "Failed to deserialize credential grants from stored job: {}. \
+                 Restarted job will have no credentials.",
+                e
+            );
+            vec![]
+        });
+
     let project_dir = std::path::PathBuf::from(&old_job.project_dir);
     let _token = jm
-        .create_job(new_job_id, &old_job.task, Some(project_dir), mode)
+        .create_job(
+            new_job_id,
+            &old_job.task,
+            Some(project_dir),
+            mode,
+            credential_grants,
+        )
         .await
         .map_err(|e| {
             (
@@ -1391,7 +1443,7 @@ async fn jobs_events_handler(
     }
 
     let events = store
-        .list_job_events(job_id)
+        .list_job_events(job_id, None)
         .await
         .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
 
@@ -1544,10 +1596,7 @@ async fn job_files_read_handler(
 
 async fn logs_events_handler(
     State(state): State<Arc<GatewayState>>,
-) -> Result<
-    Sse<impl futures::Stream<Item = Result<Event, Infallible>> + Send + 'static>,
-    (StatusCode, String),
-> {
+) -> Result<impl IntoResponse, (StatusCode, String)> {
     let broadcaster = state.log_broadcaster.as_ref().ok_or((
         StatusCode::SERVICE_UNAVAILABLE,
         "Log broadcaster not available".to_string(),
@@ -1560,25 +1609,60 @@ async fn logs_events_handler(
 
     let history_stream = futures::stream::iter(history).map(|entry| {
         let data = serde_json::to_string(&entry).unwrap_or_default();
-        Ok(Event::default().event("log").data(data))
+        Ok::<_, Infallible>(Event::default().event("log").data(data))
     });
 
     let live_stream = tokio_stream::wrappers::BroadcastStream::new(rx)
         .filter_map(|result| result.ok())
         .map(|entry| {
             let data = serde_json::to_string(&entry).unwrap_or_default();
-            Ok(Event::default().event("log").data(data))
+            Ok::<_, Infallible>(Event::default().event("log").data(data))
         });
 
     let stream = history_stream.chain(live_stream);
 
-    Ok(Sse::new(stream).keep_alive(
-        KeepAlive::new()
-            .interval(std::time::Duration::from_secs(30))
-            .text(""),
+    Ok((
+        [("X-Accel-Buffering", "no"), ("Cache-Control", "no-cache")],
+        Sse::new(stream).keep_alive(
+            KeepAlive::new()
+                .interval(std::time::Duration::from_secs(30))
+                .text(""),
+        ),
     ))
 }
 
+async fn logs_level_get_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let handle = state.log_level_handle.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Log level control not available".to_string(),
+    ))?;
+    Ok(Json(serde_json::json!({ "level": handle.current_level() })))
+}
+
+async fn logs_level_set_handler(
+    State(state): State<Arc<GatewayState>>,
+    Json(body): Json<serde_json::Value>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let handle = state.log_level_handle.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Log level control not available".to_string(),
+    ))?;
+
+    let level = body
+        .get("level")
+        .and_then(|v| v.as_str())
+        .ok_or((StatusCode::BAD_REQUEST, "missing 'level' field".to_string()))?;
+
+    handle
+        .set_level(level)
+        .map_err(|e| (StatusCode::BAD_REQUEST, e))?;
+
+    tracing::info!("Log level changed to '{}'", handle.current_level());
+    Ok(Json(serde_json::json!({ "level": handle.current_level() })))
+}
+
 // --- Extension handlers ---
 
 async fn extensions_list_handler(
@@ -1786,6 +1870,253 @@ async fn extensions_remove_handler(
     }
 }
 
+// --- Skills handlers ---
+
+async fn skills_list_handler(
+    State(state): State<Arc<GatewayState>>,
+) -> Result<Json<super::types::SkillListResponse>, (StatusCode, String)> {
+    let registry = state.skill_registry.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Skills system not enabled".to_string(),
+    ))?;
+
+    let guard = registry.read().map_err(|e| {
+        (
+            StatusCode::INTERNAL_SERVER_ERROR,
+            format!("Skill registry lock poisoned: {}", e),
+        )
+    })?;
+
+    let skills: Vec<super::types::SkillInfo> = guard
+        .skills()
+        .iter()
+        .map(|s| super::types::SkillInfo {
+            name: s.manifest.name.clone(),
+            description: s.manifest.description.clone(),
+            version: s.manifest.version.clone(),
+            trust: s.trust.to_string(),
+            source: format!("{:?}", s.source),
+            keywords: s.manifest.activation.keywords.clone(),
+        })
+        .collect();
+
+    let count = skills.len();
+    Ok(Json(super::types::SkillListResponse { skills, count }))
+}
+
+async fn skills_search_handler(
+    State(state): State<Arc<GatewayState>>,
+    Json(req): Json<super::types::SkillSearchRequest>,
+) -> Result<Json<super::types::SkillSearchResponse>, (StatusCode, String)> {
+    let registry = state.skill_registry.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Skills system not enabled".to_string(),
+    ))?;
+
+    let catalog = state.skill_catalog.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Skill catalog not available".to_string(),
+    ))?;
+
+    // Search ClawHub catalog
+    let catalog_results = catalog.search(&req.query).await;
+    let catalog_json: Vec<serde_json::Value> = catalog_results
+        .into_iter()
+        .map(|e| {
+            serde_json::json!({
+                "slug": e.slug,
+                "name": e.name,
+                "description": e.description,
+                "version": e.version,
+                "score": e.score,
+            })
+        })
+        .collect();
+
+    // Search local skills
+    let query_lower = req.query.to_lowercase();
+    let installed: Vec<super::types::SkillInfo> = {
+        let guard = registry.read().map_err(|e| {
+            (
+                StatusCode::INTERNAL_SERVER_ERROR,
+                format!("Skill registry lock poisoned: {}", e),
+            )
+        })?;
+        guard
+            .skills()
+            .iter()
+            .filter(|s| {
+                s.manifest.name.to_lowercase().contains(&query_lower)
+                    || s.manifest.description.to_lowercase().contains(&query_lower)
+            })
+            .map(|s| super::types::SkillInfo {
+                name: s.manifest.name.clone(),
+                description: s.manifest.description.clone(),
+                version: s.manifest.version.clone(),
+                trust: s.trust.to_string(),
+                source: format!("{:?}", s.source),
+                keywords: s.manifest.activation.keywords.clone(),
+            })
+            .collect()
+    };
+
+    Ok(Json(super::types::SkillSearchResponse {
+        catalog: catalog_json,
+        installed,
+        registry_url: catalog.registry_url().to_string(),
+    }))
+}
+
+async fn skills_install_handler(
+    State(state): State<Arc<GatewayState>>,
+    headers: axum::http::HeaderMap,
+    Json(req): Json<super::types::SkillInstallRequest>,
+) -> Result<Json<ActionResponse>, (StatusCode, String)> {
+    // Require explicit confirmation header to prevent accidental installs.
+    // Chat tools have requires_approval(); this is the equivalent for the web API.
+    if headers
+        .get("x-confirm-action")
+        .and_then(|v| v.to_str().ok())
+        != Some("true")
+    {
+        return Err((
+            StatusCode::BAD_REQUEST,
+            "Skill install requires X-Confirm-Action: true header".to_string(),
+        ));
+    }
+
+    let registry = state.skill_registry.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Skills system not enabled".to_string(),
+    ))?;
+
+    let content = if let Some(ref raw) = req.content {
+        raw.clone()
+    } else if let Some(ref url) = req.url {
+        // Fetch from explicit URL (with SSRF protection)
+        crate::tools::builtin::skill_tools::fetch_skill_content(url)
+            .await
+            .map_err(|e| (StatusCode::BAD_REQUEST, e.to_string()))?
+    } else if let Some(ref catalog) = state.skill_catalog {
+        let url = crate::skills::catalog::skill_download_url(catalog.registry_url(), &req.name);
+        crate::tools::builtin::skill_tools::fetch_skill_content(&url)
+            .await
+            .map_err(|e| (StatusCode::BAD_GATEWAY, e.to_string()))?
+    } else {
+        return Ok(Json(ActionResponse::fail(
+            "Provide 'content' or 'url' to install a skill".to_string(),
+        )));
+    };
+
+    // Parse, check duplicates, and get user_dir under a brief read lock.
+    let (user_dir, skill_name_from_parse) = {
+        let guard = registry.read().map_err(|e| {
+            (
+                StatusCode::INTERNAL_SERVER_ERROR,
+                format!("Skill registry lock poisoned: {}", e),
+            )
+        })?;
+
+        let normalized = crate::skills::normalize_line_endings(&content);
+        let parsed = crate::skills::parser::parse_skill_md(&normalized)
+            .map_err(|e| (StatusCode::BAD_REQUEST, e.to_string()))?;
+        let skill_name = parsed.manifest.name.clone();
+
+        if guard.has(&skill_name) {
+            return Ok(Json(ActionResponse::fail(format!(
+                "Skill '{}' already exists",
+                skill_name
+            ))));
+        }
+
+        (guard.user_dir().to_path_buf(), skill_name)
+    };
+
+    // Perform async I/O (write to disk, load) with no lock held.
+    let normalized = crate::skills::normalize_line_endings(&content);
+    let (skill_name, loaded_skill) =
+        crate::skills::registry::SkillRegistry::prepare_install_to_disk(
+            &user_dir,
+            &skill_name_from_parse,
+            &normalized,
+        )
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    // Commit: brief write lock for in-memory addition
+    let mut guard = registry.write().map_err(|e| {
+        (
+            StatusCode::INTERNAL_SERVER_ERROR,
+            format!("Skill registry lock poisoned: {}", e),
+        )
+    })?;
+
+    match guard.commit_install(&skill_name, loaded_skill) {
+        Ok(()) => Ok(Json(ActionResponse::ok(format!(
+            "Skill '{}' installed",
+            skill_name
+        )))),
+        Err(e) => Ok(Json(ActionResponse::fail(e.to_string()))),
+    }
+}
+
+async fn skills_remove_handler(
+    State(state): State<Arc<GatewayState>>,
+    headers: axum::http::HeaderMap,
+    Path(name): Path<String>,
+) -> Result<Json<ActionResponse>, (StatusCode, String)> {
+    // Require explicit confirmation header to prevent accidental removals.
+    if headers
+        .get("x-confirm-action")
+        .and_then(|v| v.to_str().ok())
+        != Some("true")
+    {
+        return Err((
+            StatusCode::BAD_REQUEST,
+            "Skill removal requires X-Confirm-Action: true header".to_string(),
+        ));
+    }
+
+    let registry = state.skill_registry.as_ref().ok_or((
+        StatusCode::NOT_IMPLEMENTED,
+        "Skills system not enabled".to_string(),
+    ))?;
+
+    // Validate removal under a brief read lock
+    let skill_path = {
+        let guard = registry.read().map_err(|e| {
+            (
+                StatusCode::INTERNAL_SERVER_ERROR,
+                format!("Skill registry lock poisoned: {}", e),
+            )
+        })?;
+        guard
+            .validate_remove(&name)
+            .map_err(|e| (StatusCode::BAD_REQUEST, e.to_string()))?
+    };
+
+    // Delete files from disk (async I/O, no lock held)
+    crate::skills::registry::SkillRegistry::delete_skill_files(&skill_path)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    // Remove from in-memory registry under a brief write lock
+    let mut guard = registry.write().map_err(|e| {
+        (
+            StatusCode::INTERNAL_SERVER_ERROR,
+            format!("Skill registry lock poisoned: {}", e),
+        )
+    })?;
+
+    match guard.commit_remove(&name) {
+        Ok(()) => Ok(Json(ActionResponse::ok(format!(
+            "Skill '{}' removed",
+            name
+        )))),
+        Err(e) => Ok(Json(ActionResponse::fail(e.to_string()))),
+    }
+}
+
 // --- Routines handlers ---
 
 async fn routines_list_handler(

src/channels/web/static/app.js

@@ -12,6 +12,7 @@ let loadingOlder = false;
 let jobEvents = new Map(); // job_id -> Array of events
 let jobListRefreshTimer = null;
 const JOB_EVENTS_CAP = 500;
+const MEMORY_SEARCH_QUERY_MAX_LENGTH = 100;
 
 // --- Auth ---
 
@@ -28,16 +29,25 @@ function authenticate() {
       sessionStorage.setItem('ironclaw_token', token);
       document.getElementById('auth-screen').style.display = 'none';
       document.getElementById('app').style.display = 'flex';
-      // Strip token from URL so it's not visible in the address bar
+      // Strip token and log_level from URL so they're not visible in the address bar
       const cleaned = new URL(window.location);
+      const urlLogLevel = cleaned.searchParams.get('log_level');
       cleaned.searchParams.delete('token');
+      cleaned.searchParams.delete('log_level');
       window.history.replaceState({}, '', cleaned.pathname + cleaned.search);
       connectSSE();
       connectLogSSE();
       startGatewayStatusPolling();
+      checkTeeStatus();
       loadThreads();
       loadMemoryTree();
       loadJobs();
+      // Apply URL log_level param if present, otherwise just sync the dropdown
+      if (urlLogLevel) {
+        setServerLogLevel(urlLogLevel);
+      } else {
+        loadServerLogLevel();
+      }
     })
     .catch(() => {
       sessionStorage.removeItem('ironclaw_token');
@@ -158,6 +168,7 @@ function connectSSE() {
 
   eventSource.addEventListener('approval_needed', (e) => {
     const data = JSON.parse(e.data);
+    if (!isCurrentThread(data.thread_id)) return;
     showApproval(data);
   });
 
@@ -1001,9 +1012,12 @@ function buildBreadcrumb(path) {
 }
 
 function searchMemory(query) {
+  const normalizedQuery = normalizeSearchQuery(query);
+  if (!normalizedQuery) return;
+
   apiFetch('/api/memory/search', {
     method: 'POST',
-    body: { query, limit: 20 },
+    body: { query: normalizedQuery, limit: 20 },
   }).then((data) => {
     const tree = document.getElementById('memory-tree');
     tree.innerHTML = '';
@@ -1014,18 +1028,23 @@ function searchMemory(query) {
     for (const result of data.results) {
       const item = document.createElement('div');
       item.className = 'search-result';
-      const snippet = snippetAround(result.content, query, 120);
+      const snippet = snippetAround(result.content, normalizedQuery, 120);
       item.innerHTML = '<div class="path">' + escapeHtml(result.path) + '</div>'
-        + '<div class="snippet">' + highlightQuery(snippet, query) + '</div>';
+        + '<div class="snippet">' + highlightQuery(snippet, normalizedQuery) + '</div>';
       item.addEventListener('click', () => readMemoryFile(result.path));
       tree.appendChild(item);
     }
   }).catch(() => {});
 }
 
+function normalizeSearchQuery(query) {
+  return (typeof query === 'string' ? query : '').slice(0, MEMORY_SEARCH_QUERY_MAX_LENGTH);
+}
+
 function snippetAround(text, query, len) {
+  const normalizedQuery = normalizeSearchQuery(query);
   const lower = text.toLowerCase();
-  const idx = lower.indexOf(query.toLowerCase());
+  const idx = lower.indexOf(normalizedQuery.toLowerCase());
   if (idx < 0) return text.substring(0, len);
   const start = Math.max(0, idx - Math.floor(len / 2));
   const end = Math.min(text.length, start + len);
@@ -1038,11 +1057,11 @@ function snippetAround(text, query, len) {
 function highlightQuery(text, query) {
   if (!query) return escapeHtml(text);
   const escaped = escapeHtml(text);
-  const queryEscaped = query.replace(/[.*+?^${}()|[\]\\]/g, '\\$&');
+  const normalizedQuery = normalizeSearchQuery(query);
+  const queryEscaped = normalizedQuery.replace(/[.*+?^${}()|[\]\\]/g, '\\$&');
   const re = new RegExp('(' + queryEscaped + ')', 'gi');
   return escaped.replace(re, '<mark>$1</mark>');
 }
-
 // --- Logs ---
 
 const LOG_MAX_ENTRIES = 2000;
@@ -1157,6 +1176,30 @@ function applyLogFilters() {
   }
 }
 
+// --- Server-side log level control ---
+
+function setServerLogLevel(level) {
+  apiFetch('/api/logs/level', {
+    method: 'PUT',
+    headers: { 'Content-Type': 'application/json' },
+    body: JSON.stringify({ level: level }),
+  })
+    .then(r => r.json())
+    .then(data => {
+      document.getElementById('logs-server-level').value = data.level;
+    })
+    .catch(err => console.error('Failed to set server log level:', err));
+}
+
+function loadServerLogLevel() {
+  apiFetch('/api/logs/level')
+    .then(r => r.json())
+    .then(data => {
+      document.getElementById('logs-server-level').value = data.level;
+    })
+    .catch(() => {}); // ignore if not available
+}
+
 // --- Extensions ---
 
 function loadExtensions() {
@@ -2056,6 +2099,100 @@ document.getElementById('gateway-status-trigger').addEventListener('mouseleave',
   document.getElementById('gateway-popover').classList.remove('visible');
 });
 
+// --- TEE attestation ---
+
+let teeInfo = null;
+let teeReportCache = null;
+let teeReportLoading = false;
+
+function teeApiBase() {
+  var parts = window.location.hostname.split('.');
+  if (parts.length < 2) return null;
+  var domain = parts.slice(1).join('.');
+  return window.location.protocol + '//api.' + domain;
+}
+
+function teeInstanceName() {
+  return window.location.hostname.split('.')[0];
+}
+
+function checkTeeStatus() {
+  var base = teeApiBase();
+  if (!base) return;
+  var name = teeInstanceName();
+  fetch(base + '/instances/' + encodeURIComponent(name) + '/attestation').then(function(res) {
+    if (!res.ok) throw new Error(res.status);
+    return res.json();
+  }).then(function(data) {
+    teeInfo = data;
+    document.getElementById('tee-shield').style.display = 'flex';
+  }).catch(function() {});
+}
+
+function fetchTeeReport() {
+  if (teeReportCache) {
+    renderTeePopover(teeReportCache);
+    return;
+  }
+  if (teeReportLoading) return;
+  teeReportLoading = true;
+  var base = teeApiBase();
+  if (!base) return;
+  var popover = document.getElementById('tee-popover');
+  popover.innerHTML = '<div class="tee-popover-loading">Loading attestation report...</div>';
+  fetch(base + '/attestation/report').then(function(res) {
+    if (!res.ok) throw new Error(res.status);
+    return res.json();
+  }).then(function(data) {
+    teeReportCache = data;
+    renderTeePopover(data);
+  }).catch(function() {
+    popover.innerHTML = '<div class="tee-popover-loading">Could not load attestation report</div>';
+  }).finally(function() {
+    teeReportLoading = false;
+  });
+}
+
+function renderTeePopover(report) {
+  var popover = document.getElementById('tee-popover');
+  var digest = (teeInfo && teeInfo.image_digest) || 'N/A';
+  var fingerprint = report.tls_certificate_fingerprint || 'N/A';
+  var reportData = report.report_data || '';
+  var vmConfig = report.vm_config || 'N/A';
+  var truncated = reportData.length > 32 ? reportData.slice(0, 32) + '...' : reportData;
+  popover.innerHTML = '<div class="tee-popover-title">'
+    + '<svg width="14" height="14" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round"><path d="M12 22s8-4 8-10V5l-8-3-8 3v7c0 6 8 10 8 10z"/></svg>'
+    + 'TEE Attestation</div>'
+    + '<div class="tee-field"><div class="tee-field-label">Image Digest</div>'
+    + '<div class="tee-field-value">' + escapeHtml(digest) + '</div></div>'
+    + '<div class="tee-field"><div class="tee-field-label">TLS Certificate Fingerprint</div>'
+    + '<div class="tee-field-value">' + escapeHtml(fingerprint) + '</div></div>'
+    + '<div class="tee-field"><div class="tee-field-label">Report Data</div>'
+    + '<div class="tee-field-value">' + escapeHtml(truncated) + '</div></div>'
+    + '<div class="tee-field"><div class="tee-field-label">VM Config</div>'
+    + '<div class="tee-field-value">' + escapeHtml(vmConfig) + '</div></div>'
+    + '<div class="tee-popover-actions">'
+    + '<button class="tee-btn-copy" onclick="copyTeeReport()">Copy Full Report</button></div>';
+}
+
+function copyTeeReport() {
+  if (!teeReportCache) return;
+  var combined = Object.assign({}, teeReportCache, teeInfo || {});
+  navigator.clipboard.writeText(JSON.stringify(combined, null, 2)).then(function() {
+    showToast('Attestation report copied', 'success');
+  }).catch(function() {
+    showToast('Failed to copy report', 'error');
+  });
+}
+
+document.getElementById('tee-shield').addEventListener('mouseenter', function() {
+  fetchTeeReport();
+  document.getElementById('tee-popover').classList.add('visible');
+});
+document.getElementById('tee-shield').addEventListener('mouseleave', function() {
+  document.getElementById('tee-popover').classList.remove('visible');
+});
+
 // --- Extension install ---
 
 function installExtension() {

src/channels/web/static/index.html

@@ -5,7 +5,11 @@
   <meta name="viewport" content="width=device-width, initial-scale=1.0">
   <title>IronClaw</title>
   <link rel="stylesheet" href="/style.css">
-  <script src="https://cdn.jsdelivr.net/npm/marked/marked.min.js"></script>
+  <script
+    src="https://cdn.jsdelivr.net/npm/[email protected]/lib/marked.umd.min.js"
+    integrity="sha384-pN9zSKOnTZwXRtYZAu0PBPEgR2B7DOC1aeLxQ33oJ0oy5iN1we6gm57xldM2irDG"
+    crossorigin="anonymous"
+  ></script>
 </head>
 <body>
   <!-- Auth Screen -->
@@ -36,6 +40,13 @@
       <button data-tab="routines">Routines</button>
       <button data-tab="extensions">Extensions</button>
       <div class="spacer"></div>
+      <div class="tee-shield" id="tee-shield" style="display:none" title="Running in a Trusted Execution Environment">
+        <svg width="16" height="16" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2" stroke-linecap="round" stroke-linejoin="round">
+          <path d="M12 22s8-4 8-10V5l-8-3-8 3v7c0 6 8 10 8 10z"/>
+        </svg>
+        <span id="tee-shield-label">TEE Verified</span>
+        <div class="tee-popover" id="tee-popover"></div>
+      </div>
       <div class="status" id="gateway-status-trigger">
         <div class="dot" id="sse-dot"></div>
         <span id="sse-status">Connected</span>
@@ -123,6 +134,12 @@
     <div class="tab-panel" id="tab-logs">
       <div class="logs-container">
         <div class="logs-toolbar">
+          <select id="logs-server-level" onchange="setServerLogLevel(this.value)" title="Server-side log level (changes what the server emits)">
+            <option value="error">Server: ERROR</option>
+            <option value="warn">Server: WARN</option>
+            <option value="info" selected>Server: INFO</option>
+            <option value="debug">Server: DEBUG</option>
+          </select>
           <select id="logs-level-filter">
             <option value="all">All Levels</option>
             <option value="ERROR">Error</option>

src/channels/web/static/style.css

@@ -189,6 +189,126 @@ body {
   background: var(--danger);
 }
 
+/* TEE Shield */
+.tee-shield {
+  display: flex;
+  align-items: center;
+  gap: 6px;
+  font-size: 12px;
+  color: var(--success);
+  padding: 4px 10px;
+  border-radius: 12px;
+  background: rgba(63, 185, 80, 0.1);
+  border: 1px solid rgba(63, 185, 80, 0.25);
+  cursor: pointer;
+  position: relative;
+  margin-right: 8px;
+  transition: background 0.15s;
+}
+
+.tee-shield:hover {
+  background: rgba(63, 185, 80, 0.18);
+}
+
+.tee-shield svg {
+  flex-shrink: 0;
+}
+
+#tee-shield-label {
+  font-weight: 500;
+  white-space: nowrap;
+}
+
+.tee-popover {
+  display: none;
+  position: absolute;
+  top: 100%;
+  right: 0;
+  margin-top: 8px;
+  background: var(--bg-secondary);
+  border: 1px solid var(--border);
+  border-radius: var(--radius);
+  padding: 16px;
+  min-width: 340px;
+  max-width: 420px;
+  z-index: 100;
+  box-shadow: var(--shadow);
+}
+
+.tee-popover.visible {
+  display: block;
+}
+
+.tee-popover-title {
+  font-size: 13px;
+  font-weight: 600;
+  color: var(--text);
+  margin-bottom: 12px;
+  display: flex;
+  align-items: center;
+  gap: 6px;
+}
+
+.tee-popover-title svg {
+  color: var(--success);
+}
+
+.tee-field {
+  margin-bottom: 10px;
+}
+
+.tee-field:last-child {
+  margin-bottom: 0;
+}
+
+.tee-field-label {
+  font-size: 11px;
+  font-weight: 500;
+  color: var(--text-secondary);
+  text-transform: uppercase;
+  letter-spacing: 0.5px;
+  margin-bottom: 3px;
+}
+
+.tee-field-value {
+  font-size: 12px;
+  font-family: "SFMono-Regular", Consolas, "Liberation Mono", Menlo, monospace;
+  color: var(--text);
+  word-break: break-all;
+  background: var(--bg);
+  padding: 4px 8px;
+  border-radius: 4px;
+  border: 1px solid var(--border);
+}
+
+.tee-popover-actions {
+  margin-top: 12px;
+  display: flex;
+  gap: 8px;
+}
+
+.tee-btn-copy {
+  padding: 4px 10px;
+  background: none;
+  border: 1px solid var(--border);
+  border-radius: var(--radius);
+  color: var(--text-secondary);
+  cursor: pointer;
+  font-size: 11px;
+  transition: color 0.15s, border-color 0.15s;
+}
+
+.tee-btn-copy:hover {
+  color: var(--text);
+  border-color: var(--text-secondary);
+}
+
+.tee-popover-loading {
+  font-size: 12px;
+  color: var(--text-secondary);
+  padding: 8px 0;
+}
+
 /* Tab Panels */
 .tab-panel {
   display: none;

src/channels/web/types.rs

@@ -137,6 +137,8 @@ pub enum SseEvent {
         tool_name: String,
         description: String,
         parameters: String,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        thread_id: Option<String>,
     },
     #[serde(rename = "auth_required")]
     AuthRequired {
@@ -406,6 +408,43 @@ impl ActionResponse {
     }
 }
 
+// --- Skills ---
+
+#[derive(Debug, Serialize)]
+pub struct SkillInfo {
+    pub name: String,
+    pub description: String,
+    pub version: String,
+    pub trust: String,
+    pub source: String,
+    pub keywords: Vec<String>,
+}
+
+#[derive(Debug, Serialize)]
+pub struct SkillListResponse {
+    pub skills: Vec<SkillInfo>,
+    pub count: usize,
+}
+
+#[derive(Debug, Deserialize)]
+pub struct SkillSearchRequest {
+    pub query: String,
+}
+
+#[derive(Debug, Serialize)]
+pub struct SkillSearchResponse {
+    pub catalog: Vec<serde_json::Value>,
+    pub installed: Vec<SkillInfo>,
+    pub registry_url: String,
+}
+
+#[derive(Debug, Deserialize)]
+pub struct SkillInstallRequest {
+    pub name: String,
+    pub url: Option<String>,
+    pub content: Option<String>,
+}
+
 // --- Auth Token ---
 
 /// Request to submit an auth token for an extension (dedicated endpoint).
@@ -748,12 +787,14 @@ mod tests {
             tool_name: "shell".to_string(),
             description: "Run ls".to_string(),
             parameters: "{}".to_string(),
+            thread_id: Some("t1".to_string()),
         };
         let ws = WsServerMessage::from_sse_event(&sse);
         match ws {
             WsServerMessage::Event { event_type, data } => {
                 assert_eq!(event_type, "approval_needed");
                 assert_eq!(data["tool_name"], "shell");
+                assert_eq!(data["thread_id"], "t1");
             }
             _ => panic!("Expected Event variant"),
         }

src/channels/web/ws.rs

@@ -477,6 +477,7 @@ mod tests {
             workspace: None,
             session_manager: None,
             log_broadcaster: None,
+            log_level_handle: None,
             extension_manager: None,
             tool_registry: None,
             store: None,
@@ -486,6 +487,8 @@ mod tests {
             shutdown_tx: tokio::sync::RwLock::new(None),
             ws_tracker: Some(Arc::new(WsConnectionTracker::new())),
             llm_provider: None,
+            skill_registry: None,
+            skill_catalog: None,
             chat_rate_limiter: crate::channels::web::server::RateLimiter::new(30, 60),
         }
     }

src/cli/config.rs

@@ -11,6 +11,17 @@ use crate::settings::Settings;
 
 #[derive(Subcommand, Debug, Clone)]
 pub enum ConfigCommand {
+    /// Generate a default config.toml file
+    Init {
+        /// Output path (default: ~/.ironclaw/config.toml)
+        #[arg(short, long)]
+        output: Option<std::path::PathBuf>,
+
+        /// Overwrite existing file
+        #[arg(long)]
+        force: bool,
+    },
+
     /// List all settings and their current values
     List {
         /// Show only settings matching this prefix (e.g., "agent", "heartbeat")
@@ -62,6 +73,7 @@ pub async fn run_config_command(cmd: ConfigCommand) -> anyhow::Result<()> {
 
     let db_ref = db.as_deref();
     match cmd {
+        ConfigCommand::Init { output, force } => init_toml(db_ref, output, force).await,
         ConfigCommand::List { filter } => list_settings(db_ref, filter).await,
         ConfigCommand::Get { path } => get_setting(db_ref, &path).await,
         ConfigCommand::Set { path, value } => set_setting(db_ref, &path, &value).await,
@@ -188,6 +200,36 @@ async fn reset_setting(store: Option<&dyn crate::db::Database>, path: &str) -> a
     Ok(())
 }
 
+/// Generate a default TOML config file.
+async fn init_toml(
+    store: Option<&dyn crate::db::Database>,
+    output: Option<std::path::PathBuf>,
+    force: bool,
+) -> anyhow::Result<()> {
+    let path = output.unwrap_or_else(Settings::default_toml_path);
+
+    if path.exists() && !force {
+        anyhow::bail!(
+            "Config file already exists: {}\nUse --force to overwrite.",
+            path.display()
+        );
+    }
+
+    // Start from current settings (DB or defaults) so the generated file
+    // reflects the user's existing configuration.
+    let settings = load_settings(store).await;
+
+    settings
+        .save_toml(&path)
+        .map_err(|e| anyhow::anyhow!("{}", e))?;
+
+    println!("Config file written to {}", path.display());
+    println!();
+    println!("Edit the file to customize settings.");
+    println!("Priority: env var > config.toml > database > defaults");
+    Ok(())
+}
+
 /// Show the settings storage info.
 fn show_path(has_db: bool) -> anyhow::Result<()> {
     if has_db {
@@ -200,6 +242,18 @@ fn show_path(has_db: bool) -> anyhow::Result<()> {
         crate::bootstrap::ironclaw_env_path().display()
     );
 
+    let toml_path = Settings::default_toml_path();
+    let toml_status = if toml_path.exists() {
+        "found"
+    } else {
+        "not found (run `ironclaw config init` to create)"
+    };
+    println!(
+        "TOML config:        {} ({})",
+        toml_path.display(),
+        toml_status
+    );
+
     Ok(())
 }
 
@@ -230,4 +284,39 @@ mod tests {
         settings.reset("agent.name").unwrap();
         assert_eq!(settings.agent.name, "ironclaw");
     }
+
+    #[tokio::test]
+    async fn init_toml_creates_file() {
+        let dir = tempdir().unwrap();
+        let path = dir.path().join("config.toml");
+
+        init_toml(None, Some(path.clone()), false).await.unwrap();
+        assert!(path.exists());
+
+        let content = std::fs::read_to_string(&path).unwrap();
+        assert!(content.contains("[agent]"));
+    }
+
+    #[tokio::test]
+    async fn init_toml_refuses_overwrite_without_force() {
+        let dir = tempdir().unwrap();
+        let path = dir.path().join("config.toml");
+        std::fs::write(&path, "existing").unwrap();
+
+        let result = init_toml(None, Some(path.clone()), false).await;
+        assert!(result.is_err());
+        assert!(result.unwrap_err().to_string().contains("already exists"));
+    }
+
+    #[tokio::test]
+    async fn init_toml_force_overwrites() {
+        let dir = tempdir().unwrap();
+        let path = dir.path().join("config.toml");
+        std::fs::write(&path, "old content").unwrap();
+
+        init_toml(None, Some(path.clone()), true).await.unwrap();
+
+        let content = std::fs::read_to_string(&path).unwrap();
+        assert!(content.contains("[agent]"));
+    }
 }

src/cli/doctor.rs

@@ -0,0 +1,287 @@
+//! `ironclaw doctor` - active health diagnostics.
+//!
+//! Probes external dependencies and validates configuration to surface
+//! problems before they bite during normal operation. Each check reports
+//! pass/fail with actionable guidance on failures.
+
+use std::path::PathBuf;
+
+/// Run all diagnostic checks and print results.
+pub async fn run_doctor_command() -> anyhow::Result<()> {
+    println!("IronClaw Doctor");
+    println!("===============\n");
+
+    let mut passed = 0u32;
+    let mut failed = 0u32;
+
+    // ── Configuration checks ──────────────────────────────────
+
+    check(
+        "NEAR AI session",
+        check_nearai_session().await,
+        &mut passed,
+        &mut failed,
+    );
+
+    check(
+        "Database backend",
+        check_database().await,
+        &mut passed,
+        &mut failed,
+    );
+
+    check(
+        "Workspace directory",
+        check_workspace_dir(),
+        &mut passed,
+        &mut failed,
+    );
+
+    // ── External binary checks ────────────────────────────────
+
+    check(
+        "Docker",
+        check_binary("docker", &["--version"]),
+        &mut passed,
+        &mut failed,
+    );
+
+    check(
+        "cloudflared",
+        check_binary("cloudflared", &["--version"]),
+        &mut passed,
+        &mut failed,
+    );
+
+    check(
+        "ngrok",
+        check_binary("ngrok", &["version"]),
+        &mut passed,
+        &mut failed,
+    );
+
+    check(
+        "tailscale",
+        check_binary("tailscale", &["version"]),
+        &mut passed,
+        &mut failed,
+    );
+
+    // ── Summary ───────────────────────────────────────────────
+
+    println!();
+    println!("  {passed} passed, {failed} failed");
+
+    if failed > 0 {
+        println!("\n  Some checks failed. This is normal if you don't use those features.");
+    }
+
+    Ok(())
+}
+
+// ── Individual checks ───────────────────────────────────────
+
+fn check(name: &str, result: CheckResult, passed: &mut u32, failed: &mut u32) {
+    match result {
+        CheckResult::Pass(detail) => {
+            *passed += 1;
+            println!("  [pass] {name}: {detail}");
+        }
+        CheckResult::Fail(detail) => {
+            *failed += 1;
+            println!("  [FAIL] {name}: {detail}");
+        }
+        CheckResult::Skip(reason) => {
+            println!("  [skip] {name}: {reason}");
+        }
+    }
+}
+
+enum CheckResult {
+    Pass(String),
+    Fail(String),
+    Skip(String),
+}
+
+async fn check_nearai_session() -> CheckResult {
+    // Check if session file exists
+    let session_path = crate::llm::session::default_session_path();
+    if !session_path.exists() {
+        // Check for API key mode
+        if std::env::var("NEARAI_API_KEY").is_ok() {
+            return CheckResult::Pass("API key configured".into());
+        }
+        return CheckResult::Fail(format!(
+            "session file not found at {}. Run `ironclaw onboard`",
+            session_path.display()
+        ));
+    }
+
+    // Verify the session file is readable and non-empty
+    match std::fs::read_to_string(&session_path) {
+        Ok(content) if content.trim().is_empty() => {
+            CheckResult::Fail("session file is empty".into())
+        }
+        Ok(_) => CheckResult::Pass(format!("session found ({})", session_path.display())),
+        Err(e) => CheckResult::Fail(format!("cannot read session file: {e}")),
+    }
+}
+
+async fn check_database() -> CheckResult {
+    let backend = std::env::var("DATABASE_BACKEND")
+        .ok()
+        .unwrap_or_else(|| "postgres".into());
+
+    match backend.as_str() {
+        "libsql" | "turso" | "sqlite" => {
+            let path = std::env::var("LIBSQL_PATH")
+                .map(PathBuf::from)
+                .unwrap_or_else(|_| crate::config::default_libsql_path());
+
+            if path.exists() {
+                CheckResult::Pass(format!("libSQL database exists ({})", path.display()))
+            } else {
+                CheckResult::Pass(format!(
+                    "libSQL database not found at {} (will be created on first run)",
+                    path.display()
+                ))
+            }
+        }
+        _ => {
+            if std::env::var("DATABASE_URL").is_ok() {
+                // Try to connect
+                match try_pg_connect().await {
+                    Ok(()) => CheckResult::Pass("PostgreSQL connected".into()),
+                    Err(e) => CheckResult::Fail(format!("PostgreSQL connection failed: {e}")),
+                }
+            } else {
+                CheckResult::Fail("DATABASE_URL not set".into())
+            }
+        }
+    }
+}
+
+#[cfg(feature = "postgres")]
+async fn try_pg_connect() -> Result<(), String> {
+    let url = std::env::var("DATABASE_URL").map_err(|_| "DATABASE_URL not set".to_string())?;
+
+    let config = deadpool_postgres::Config {
+        url: Some(url),
+        ..Default::default()
+    };
+    let pool = config
+        .create_pool(
+            Some(deadpool_postgres::Runtime::Tokio1),
+            tokio_postgres::NoTls,
+        )
+        .map_err(|e| format!("pool error: {e}"))?;
+
+    let client = tokio::time::timeout(std::time::Duration::from_secs(5), pool.get())
+        .await
+        .map_err(|_| "connection timeout (5s)".to_string())?
+        .map_err(|e| format!("{e}"))?;
+
+    client
+        .execute("SELECT 1", &[])
+        .await
+        .map_err(|e| format!("{e}"))?;
+
+    Ok(())
+}
+
+#[cfg(not(feature = "postgres"))]
+async fn try_pg_connect() -> Result<(), String> {
+    Err("postgres feature not compiled in".into())
+}
+
+fn check_workspace_dir() -> CheckResult {
+    let dir = dirs::home_dir()
+        .unwrap_or_else(|| PathBuf::from("."))
+        .join(".ironclaw");
+
+    if dir.exists() {
+        if dir.is_dir() {
+            CheckResult::Pass(format!("{}", dir.display()))
+        } else {
+            CheckResult::Fail(format!("{} exists but is not a directory", dir.display()))
+        }
+    } else {
+        CheckResult::Pass(format!("{} will be created on first run", dir.display()))
+    }
+}
+
+fn check_binary(name: &str, args: &[&str]) -> CheckResult {
+    match std::process::Command::new(name)
+        .args(args)
+        .stdout(std::process::Stdio::piped())
+        .stderr(std::process::Stdio::piped())
+        .output()
+    {
+        Ok(output) => {
+            let version = String::from_utf8_lossy(&output.stdout);
+            let version = version.trim();
+            // Some tools print version to stderr
+            let version = if version.is_empty() {
+                let stderr = String::from_utf8_lossy(&output.stderr);
+                stderr.trim().lines().next().unwrap_or("").to_string()
+            } else {
+                version.lines().next().unwrap_or("").to_string()
+            };
+
+            if output.status.success() {
+                CheckResult::Pass(version)
+            } else {
+                CheckResult::Fail(format!("exited with {}", output.status))
+            }
+        }
+        Err(_) => CheckResult::Skip(format!("{name} not found in PATH")),
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use crate::cli::doctor::*;
+
+    #[test]
+    fn check_binary_finds_sh() {
+        match check_binary("sh", &["-c", "echo ok"]) {
+            CheckResult::Pass(_) => {}
+            other => panic!("expected Pass for sh, got: {}", format_result(&other)),
+        }
+    }
+
+    #[test]
+    fn check_binary_skips_nonexistent() {
+        match check_binary("__ironclaw_nonexistent_binary__", &["--version"]) {
+            CheckResult::Skip(_) => {}
+            other => panic!(
+                "expected Skip for nonexistent binary, got: {}",
+                format_result(&other)
+            ),
+        }
+    }
+
+    #[test]
+    fn check_workspace_dir_does_not_panic() {
+        let result = check_workspace_dir();
+        match result {
+            CheckResult::Pass(_) | CheckResult::Fail(_) | CheckResult::Skip(_) => {}
+        }
+    }
+
+    #[tokio::test]
+    async fn check_nearai_session_does_not_panic() {
+        let result = check_nearai_session().await;
+        match result {
+            CheckResult::Pass(_) | CheckResult::Fail(_) | CheckResult::Skip(_) => {}
+        }
+    }
+
+    fn format_result(r: &CheckResult) -> String {
+        match r {
+            CheckResult::Pass(s) => format!("Pass({s})"),
+            CheckResult::Fail(s) => format!("Fail({s})"),
+            CheckResult::Skip(s) => format!("Skip({s})"),
+        }
+    }
+}

src/cli/mcp.rs

@@ -519,7 +519,7 @@ async fn get_secrets_store() -> anyhow::Result<Arc<dyn SecretsStore + Send + Syn
     #[cfg(all(feature = "libsql", not(feature = "postgres")))]
     {
         use crate::db::Database as _;
-        use crate::db::libsql_backend::LibSqlBackend;
+        use crate::db::libsql::LibSqlBackend;
         use secrecy::ExposeSecret as _;
 
         let default_path = crate::config::default_libsql_path();

src/cli/mod.rs

@@ -7,23 +7,31 @@
 //! - Managing WASM tools (`tool install`, `tool list`, `tool remove`)
 //! - Managing MCP servers (`mcp add`, `mcp auth`, `mcp list`, `mcp test`)
 //! - Querying workspace memory (`memory search`, `memory read`, `memory write`)
+//! - Managing OS service (`service install`, `service start`, `service stop`)
+//! - Active health diagnostics (`doctor`)
 //! - Checking system health (`status`)
 
 mod config;
+mod doctor;
 mod mcp;
 pub mod memory;
 pub mod oauth_defaults;
 mod pairing;
+mod registry;
+mod service;
 pub mod status;
 mod tool;
 
 pub use config::{ConfigCommand, run_config_command};
+pub use doctor::run_doctor_command;
 pub use mcp::{McpCommand, run_mcp_command};
 pub use memory::MemoryCommand;
 #[cfg(feature = "postgres")]
 pub use memory::run_memory_command;
 pub use memory::run_memory_command_with_db;
 pub use pairing::{PairingCommand, run_pairing_command, run_pairing_command_with_store};
+pub use registry::{RegistryCommand, run_registry_command};
+pub use service::{ServiceCommand, run_service_command};
 pub use status::run_status_command;
 pub use tool::{ToolCommand, run_tool_command};
 
@@ -84,6 +92,10 @@ pub enum Command {
     #[command(subcommand)]
     Tool(ToolCommand),
 
+    /// Browse and install extensions from the registry
+    #[command(subcommand)]
+    Registry(RegistryCommand),
+
     /// Manage MCP servers (hosted tool providers)
     #[command(subcommand)]
     Mcp(McpCommand),
@@ -96,6 +108,13 @@ pub enum Command {
     #[command(subcommand)]
     Pairing(PairingCommand),
 
+    /// Manage OS service (launchd / systemd)
+    #[command(subcommand)]
+    Service(ServiceCommand),
+
+    /// Probe external dependencies and validate configuration
+    Doctor,
+
     /// Show system health and diagnostics
     Status,
 

src/cli/oauth_defaults.rs

@@ -62,6 +62,18 @@ pub fn builtin_credentials(secret_name: &str) -> Option<OAuthCredentials> {
 /// `http://localhost:9876/callback` (or `/auth/callback` for NEAR AI).
 pub const OAUTH_CALLBACK_PORT: u16 = 9876;
 
+/// Returns the OAuth callback base URL.
+///
+/// Checks `IRONCLAW_OAUTH_CALLBACK_URL` env var first (useful for remote/VPS
+/// deployments where `127.0.0.1` is unreachable from the user's browser),
+/// then falls back to `http://127.0.0.1:{OAUTH_CALLBACK_PORT}`.
+pub fn callback_url() -> String {
+    std::env::var("IRONCLAW_OAUTH_CALLBACK_URL")
+        .ok()
+        .filter(|v| !v.is_empty())
+        .unwrap_or_else(|| format!("http://127.0.0.1:{}", OAUTH_CALLBACK_PORT))
+}
+
 /// Error from the OAuth callback listener.
 #[derive(Debug, thiserror::Error)]
 pub enum OAuthCallbackError {
@@ -297,7 +309,54 @@ pub fn landing_html(provider_name: &str, success: bool) -> String {
 
 #[cfg(test)]
 mod tests {
-    use crate::cli::oauth_defaults::{builtin_credentials, landing_html};
+    use std::sync::Mutex;
+
+    use crate::cli::oauth_defaults::{builtin_credentials, callback_url, landing_html};
+
+    /// Serializes env-mutating tests to prevent parallel races.
+    static ENV_MUTEX: Mutex<()> = Mutex::new(());
+
+    #[test]
+    fn test_callback_url_default() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        // Clear the env var to test default behavior
+        let original = std::env::var("IRONCLAW_OAUTH_CALLBACK_URL").ok();
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe {
+            std::env::remove_var("IRONCLAW_OAUTH_CALLBACK_URL");
+        }
+        let url = callback_url();
+        assert_eq!(url, "http://127.0.0.1:9876");
+        // Restore
+        unsafe {
+            if let Some(val) = original {
+                std::env::set_var("IRONCLAW_OAUTH_CALLBACK_URL", val);
+            }
+        }
+    }
+
+    #[test]
+    fn test_callback_url_env_override() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        let original = std::env::var("IRONCLAW_OAUTH_CALLBACK_URL").ok();
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe {
+            std::env::set_var(
+                "IRONCLAW_OAUTH_CALLBACK_URL",
+                "https://myserver.example.com:9876",
+            );
+        }
+        let url = callback_url();
+        assert_eq!(url, "https://myserver.example.com:9876");
+        // Restore
+        unsafe {
+            if let Some(val) = original {
+                std::env::set_var("IRONCLAW_OAUTH_CALLBACK_URL", val);
+            } else {
+                std::env::remove_var("IRONCLAW_OAUTH_CALLBACK_URL");
+            }
+        }
+    }
 
     #[test]
     fn test_unknown_provider_returns_none() {

src/cli/registry.rs

@@ -0,0 +1,339 @@
+//! Registry CLI commands for discovering and installing extensions.
+
+use std::path::PathBuf;
+
+use clap::Subcommand;
+
+use crate::registry::catalog::RegistryCatalog;
+use crate::registry::installer::RegistryInstaller;
+use crate::registry::manifest::ManifestKind;
+
+#[derive(Subcommand, Debug, Clone)]
+pub enum RegistryCommand {
+    /// List available extensions in the registry
+    List {
+        /// Filter by kind: "tool" or "channel"
+        #[arg(short, long)]
+        kind: Option<String>,
+
+        /// Filter by tag (e.g. "default", "google", "messaging")
+        #[arg(short, long)]
+        tag: Option<String>,
+
+        /// Show detailed information
+        #[arg(short, long)]
+        verbose: bool,
+    },
+
+    /// Show detailed information about an extension or bundle
+    Info {
+        /// Extension or bundle name (e.g. "slack", "google", "tools/gmail")
+        name: String,
+    },
+
+    /// Install an extension or bundle from the registry
+    Install {
+        /// Extension or bundle name (e.g. "slack", "google", "default")
+        name: String,
+
+        /// Force overwrite if already installed
+        #[arg(short, long)]
+        force: bool,
+
+        /// Build from source instead of downloading pre-built artifact
+        #[arg(long)]
+        build: bool,
+    },
+
+    /// Install the default bundle of recommended extensions
+    InstallDefaults {
+        /// Force overwrite if already installed
+        #[arg(short, long)]
+        force: bool,
+
+        /// Build from source instead of downloading pre-built artifact
+        #[arg(long)]
+        build: bool,
+    },
+}
+
+/// Run a registry command.
+pub async fn run_registry_command(cmd: RegistryCommand) -> anyhow::Result<()> {
+    let registry_dir = find_registry_dir()?;
+    let catalog = RegistryCatalog::load(&registry_dir)?;
+
+    match cmd {
+        RegistryCommand::List { kind, tag, verbose } => {
+            cmd_list(&catalog, kind.as_deref(), tag.as_deref(), verbose)
+        }
+        RegistryCommand::Info { name } => cmd_info(&catalog, &name),
+        RegistryCommand::Install { name, force, build } => {
+            cmd_install(&catalog, &registry_dir, &name, force, build).await
+        }
+        RegistryCommand::InstallDefaults { force, build } => {
+            cmd_install(&catalog, &registry_dir, "default", force, build).await
+        }
+    }
+}
+
+/// Find the registry directory by looking relative to the current executable or cwd.
+fn find_registry_dir() -> anyhow::Result<PathBuf> {
+    // Try relative to current directory (for dev usage)
+    let cwd = std::env::current_dir()?;
+    let candidate = cwd.join("registry");
+    if candidate.is_dir() {
+        return Ok(candidate);
+    }
+
+    // Try relative to executable (covers installed binary, target/debug/, target/release/)
+    if let Ok(exe) = std::env::current_exe()
+        && let Some(parent) = exe.parent()
+    {
+        // Walk up to 3 levels: exe dir, parent (target/release → target), grandparent (→ repo root)
+        let mut dir = Some(parent);
+        for _ in 0..3 {
+            if let Some(d) = dir {
+                let candidate = d.join("registry");
+                if candidate.is_dir() {
+                    return Ok(candidate);
+                }
+                dir = d.parent();
+            }
+        }
+    }
+
+    // Try CARGO_MANIFEST_DIR (compile-time, works in dev builds)
+    let manifest_dir = std::path::Path::new(env!("CARGO_MANIFEST_DIR"));
+    let candidate = manifest_dir.join("registry");
+    if candidate.is_dir() {
+        return Ok(candidate);
+    }
+
+    anyhow::bail!(
+        "Could not find registry/ directory. Run from the ironclaw repo root, \
+         or ensure registry/ is next to the ironclaw binary."
+    )
+}
+
+fn cmd_list(
+    catalog: &RegistryCatalog,
+    kind: Option<&str>,
+    tag: Option<&str>,
+    verbose: bool,
+) -> anyhow::Result<()> {
+    let kind_filter = match kind {
+        Some("tool" | "tools") => Some(ManifestKind::Tool),
+        Some("channel" | "channels") => Some(ManifestKind::Channel),
+        Some(other) => anyhow::bail!("Unknown kind '{}'. Use 'tool' or 'channel'.", other),
+        None => None,
+    };
+
+    let manifests = catalog.list(kind_filter, tag);
+
+    if manifests.is_empty() {
+        println!("No extensions found matching the criteria.");
+        return Ok(());
+    }
+
+    // Print header
+    if verbose {
+        println!(
+            "{:<20} {:<8} {:<8} {:<10} DESCRIPTION",
+            "NAME", "KIND", "VERSION", "AUTH"
+        );
+        println!("{}", "-".repeat(80));
+    } else {
+        println!("{:<20} {:<8} DESCRIPTION", "NAME", "KIND");
+        println!("{}", "-".repeat(60));
+    }
+
+    for m in &manifests {
+        if verbose {
+            let auth = m
+                .auth_summary
+                .as_ref()
+                .and_then(|a| a.method.as_deref())
+                .unwrap_or("none");
+            println!(
+                "{:<20} {:<8} {:<8} {:<10} {}",
+                m.name, m.kind, m.version, auth, m.description
+            );
+        } else {
+            println!("{:<20} {:<8} {}", m.name, m.kind, m.description);
+        }
+    }
+
+    println!("\n{} extension(s) found.", manifests.len());
+
+    // Show bundles hint
+    let bundle_names = catalog.bundle_names();
+    if !bundle_names.is_empty() {
+        println!("\nBundles available: {}", bundle_names.join(", "));
+        println!("Use `ironclaw registry info <bundle>` for details.");
+    }
+
+    Ok(())
+}
+
+fn cmd_info(catalog: &RegistryCatalog, name: &str) -> anyhow::Result<()> {
+    // Check if it's a bundle
+    if let Some(bundle) = catalog.get_bundle(name) {
+        println!("Bundle: {}", bundle.display_name);
+        if let Some(desc) = &bundle.description {
+            println!("  {}", desc);
+        }
+        println!("\nExtensions:");
+        for ext_key in &bundle.extensions {
+            if let Some(m) = catalog.get(ext_key) {
+                println!("  {} - {} ({})", ext_key, m.description, m.kind);
+            } else {
+                println!("  {} (not found in registry)", ext_key);
+            }
+        }
+        if let Some(shared) = &bundle.shared_auth {
+            println!("\nShared auth: {}", shared);
+        }
+        return Ok(());
+    }
+
+    // Single extension (use get_strict to surface ambiguous bare names)
+    let manifest = catalog
+        .get_strict(name)
+        .map_err(|e| anyhow::anyhow!("{}", e))?;
+
+    println!("{} ({})", manifest.display_name, manifest.kind);
+    println!("  Version: {}", manifest.version);
+    println!("  {}", manifest.description);
+
+    if !manifest.keywords.is_empty() {
+        println!("  Keywords: {}", manifest.keywords.join(", "));
+    }
+
+    println!("\nSource:");
+    println!("  Directory: {}", manifest.source.dir);
+    println!("  Crate: {}", manifest.source.crate_name);
+    println!("  Capabilities: {}", manifest.source.capabilities);
+
+    if let Some(artifact) = manifest.artifacts.get("wasm32-wasip2") {
+        println!("\nArtifact (wasm32-wasip2):");
+        match &artifact.url {
+            Some(url) => println!("  URL: {}", url),
+            None => println!("  URL: (not yet published)"),
+        }
+        match &artifact.sha256 {
+            Some(sha) => println!("  SHA256: {}", sha),
+            None => println!("  SHA256: (not yet computed)"),
+        }
+    }
+
+    if let Some(auth) = &manifest.auth_summary {
+        println!("\nAuthentication:");
+        if let Some(method) = &auth.method {
+            println!("  Method: {}", method);
+        }
+        if let Some(provider) = &auth.provider {
+            println!("  Provider: {}", provider);
+        }
+        if !auth.secrets.is_empty() {
+            println!("  Secrets: {}", auth.secrets.join(", "));
+        }
+        if let Some(shared) = &auth.shared_auth {
+            println!("  Shared with: {}", shared);
+        }
+        if let Some(url) = &auth.setup_url {
+            println!("  Setup: {}", url);
+        }
+    }
+
+    if !manifest.tags.is_empty() {
+        println!("\nTags: {}", manifest.tags.join(", "));
+    }
+
+    Ok(())
+}
+
+async fn cmd_install(
+    catalog: &RegistryCatalog,
+    registry_dir: &std::path::Path,
+    name: &str,
+    force: bool,
+    prefer_build: bool,
+) -> anyhow::Result<()> {
+    // Registry dir parent is the repo root
+    let repo_root = registry_dir
+        .parent()
+        .ok_or_else(|| anyhow::anyhow!("Cannot determine repo root from registry dir"))?;
+
+    let installer = RegistryInstaller::with_defaults(repo_root.to_path_buf());
+
+    let (manifests, bundle) = catalog.resolve(name)?;
+
+    if manifests.is_empty() {
+        anyhow::bail!("No extensions found for '{}'.", name);
+    }
+
+    if let Some(bundle_def) = bundle {
+        // Bundle install
+        println!(
+            "Installing bundle '{}' ({} extensions)...\n",
+            bundle_def.display_name,
+            manifests.len()
+        );
+
+        let (outcomes, hints) = installer
+            .install_bundle(&manifests, bundle_def, force, prefer_build)
+            .await;
+
+        println!("\n--- Results ---");
+        for outcome in &outcomes {
+            let caps_status = if outcome.has_capabilities { "+" } else { "-" };
+            println!(
+                "  [{}] {} ({}) -> {}",
+                caps_status,
+                outcome.name,
+                outcome.kind,
+                outcome.wasm_path.display()
+            );
+            for w in &outcome.warnings {
+                println!("      Warning: {}", w);
+            }
+        }
+
+        if !hints.is_empty() {
+            println!("\nAuth setup:");
+            for hint in &hints {
+                println!("{}", hint);
+            }
+        }
+
+        println!(
+            "\nInstalled {}/{} extensions.",
+            outcomes.len(),
+            manifests.len()
+        );
+    } else {
+        // Single extension
+        let manifest = manifests[0];
+        let outcome = installer.install(manifest, force, prefer_build).await?;
+
+        println!("\nInstalled successfully:");
+        println!("  Name: {}", outcome.name);
+        println!("  Kind: {}", outcome.kind);
+        println!("  WASM: {}", outcome.wasm_path.display());
+        println!("  Capabilities: {}", outcome.has_capabilities);
+
+        if let Some(auth) = &manifest.auth_summary
+            && auth.method.as_deref() != Some("none")
+        {
+            println!(
+                "\nNext step: authenticate with `ironclaw tool auth {}`",
+                manifest.name
+            );
+            if let Some(url) = &auth.setup_url {
+                println!("  Setup credentials at: {}", url);
+            }
+        }
+    }
+
+    Ok(())
+}

src/cli/service.rs

@@ -0,0 +1,37 @@
+//! CLI subcommand definitions for `ironclaw service`.
+
+use clap::Subcommand;
+
+use crate::service::ServiceAction;
+
+#[derive(Subcommand, Debug, Clone)]
+pub enum ServiceCommand {
+    /// Install the OS service (launchd on macOS, systemd on Linux).
+    Install,
+    /// Start the installed service.
+    Start,
+    /// Stop the running service.
+    Stop,
+    /// Show service status.
+    Status,
+    /// Uninstall the OS service and remove the unit file.
+    Uninstall,
+}
+
+impl ServiceCommand {
+    /// Convert the CLI variant into the domain action.
+    pub fn to_action(&self) -> ServiceAction {
+        match self {
+            ServiceCommand::Install => ServiceAction::Install,
+            ServiceCommand::Start => ServiceAction::Start,
+            ServiceCommand::Stop => ServiceAction::Stop,
+            ServiceCommand::Status => ServiceAction::Status,
+            ServiceCommand::Uninstall => ServiceAction::Uninstall,
+        }
+    }
+}
+
+/// Run the service command.
+pub fn run_service_command(cmd: &ServiceCommand) -> anyhow::Result<()> {
+    crate::service::handle_command(&cmd.to_action())
+}

src/cli/tool.rs

@@ -737,7 +737,7 @@ async fn auth_tool(name: String, dir: Option<PathBuf>, user_id: String) -> anyho
         #[cfg(all(feature = "libsql", not(feature = "postgres")))]
         {
             use crate::db::Database as _;
-            use crate::db::libsql_backend::LibSqlBackend;
+            use crate::db::libsql::LibSqlBackend;
             use secrecy::ExposeSecret as _;
 
             let default_path = crate::config::default_libsql_path();

src/config/agent.rs

@@ -0,0 +1,140 @@
+use std::time::Duration;
+
+use crate::config::helpers::optional_env;
+use crate::error::ConfigError;
+use crate::settings::Settings;
+
+/// Agent behavior configuration.
+#[derive(Debug, Clone)]
+pub struct AgentConfig {
+    pub name: String,
+    pub max_parallel_jobs: usize,
+    pub job_timeout: Duration,
+    pub stuck_threshold: Duration,
+    pub repair_check_interval: Duration,
+    pub max_repair_attempts: u32,
+    /// Whether to use planning before tool execution.
+    pub use_planning: bool,
+    /// Session idle timeout. Sessions inactive longer than this are pruned.
+    pub session_idle_timeout: Duration,
+    /// Allow chat to use filesystem/shell tools directly (bypass sandbox).
+    pub allow_local_tools: bool,
+    /// Maximum daily LLM spend in cents (e.g. 10000 = $100). None = unlimited.
+    pub max_cost_per_day_cents: Option<u64>,
+    /// Maximum LLM/tool actions per hour. None = unlimited.
+    pub max_actions_per_hour: Option<u64>,
+    /// Maximum tool-call iterations per agentic loop invocation. Default 50.
+    pub max_tool_iterations: usize,
+    /// When true, skip tool approval checks entirely. For benchmarks/CI.
+    pub auto_approve_tools: bool,
+}
+
+impl AgentConfig {
+    pub(crate) fn resolve(settings: &Settings) -> Result<Self, ConfigError> {
+        Ok(Self {
+            name: optional_env("AGENT_NAME")?.unwrap_or_else(|| settings.agent.name.clone()),
+            max_parallel_jobs: optional_env("AGENT_MAX_PARALLEL_JOBS")?
+                .map(|s| s.parse())
+                .transpose()
+                .map_err(|e| ConfigError::InvalidValue {
+                    key: "AGENT_MAX_PARALLEL_JOBS".to_string(),
+                    message: format!("must be a positive integer: {e}"),
+                })?
+                .unwrap_or(settings.agent.max_parallel_jobs as usize),
+            job_timeout: Duration::from_secs(
+                optional_env("AGENT_JOB_TIMEOUT_SECS")?
+                    .map(|s| s.parse())
+                    .transpose()
+                    .map_err(|e| ConfigError::InvalidValue {
+                        key: "AGENT_JOB_TIMEOUT_SECS".to_string(),
+                        message: format!("must be a positive integer: {e}"),
+                    })?
+                    .unwrap_or(settings.agent.job_timeout_secs),
+            ),
+            stuck_threshold: Duration::from_secs(
+                optional_env("AGENT_STUCK_THRESHOLD_SECS")?
+                    .map(|s| s.parse())
+                    .transpose()
+                    .map_err(|e| ConfigError::InvalidValue {
+                        key: "AGENT_STUCK_THRESHOLD_SECS".to_string(),
+                        message: format!("must be a positive integer: {e}"),
+                    })?
+                    .unwrap_or(settings.agent.stuck_threshold_secs),
+            ),
+            repair_check_interval: Duration::from_secs(
+                optional_env("SELF_REPAIR_CHECK_INTERVAL_SECS")?
+                    .map(|s| s.parse())
+                    .transpose()
+                    .map_err(|e| ConfigError::InvalidValue {
+                        key: "SELF_REPAIR_CHECK_INTERVAL_SECS".to_string(),
+                        message: format!("must be a positive integer: {e}"),
+                    })?
+                    .unwrap_or(settings.agent.repair_check_interval_secs),
+            ),
+            max_repair_attempts: optional_env("SELF_REPAIR_MAX_ATTEMPTS")?
+                .map(|s| s.parse())
+                .transpose()
+                .map_err(|e| ConfigError::InvalidValue {
+                    key: "SELF_REPAIR_MAX_ATTEMPTS".to_string(),
+                    message: format!("must be a positive integer: {e}"),
+                })?
+                .unwrap_or(settings.agent.max_repair_attempts),
+            use_planning: optional_env("AGENT_USE_PLANNING")?
+                .map(|s| s.parse())
+                .transpose()
+                .map_err(|e| ConfigError::InvalidValue {
+                    key: "AGENT_USE_PLANNING".to_string(),
+                    message: format!("must be 'true' or 'false': {e}"),
+                })?
+                .unwrap_or(settings.agent.use_planning),
+            session_idle_timeout: Duration::from_secs(
+                optional_env("SESSION_IDLE_TIMEOUT_SECS")?
+                    .map(|s| s.parse())
+                    .transpose()
+                    .map_err(|e| ConfigError::InvalidValue {
+                        key: "SESSION_IDLE_TIMEOUT_SECS".to_string(),
+                        message: format!("must be a positive integer: {e}"),
+                    })?
+                    .unwrap_or(settings.agent.session_idle_timeout_secs),
+            ),
+            allow_local_tools: optional_env("ALLOW_LOCAL_TOOLS")?
+                .map(|s| s.parse())
+                .transpose()
+                .map_err(|e| ConfigError::InvalidValue {
+                    key: "ALLOW_LOCAL_TOOLS".to_string(),
+                    message: format!("must be 'true' or 'false': {e}"),
+                })?
+                .unwrap_or(false),
+            max_cost_per_day_cents: optional_env("MAX_COST_PER_DAY_CENTS")?
+                .map(|s| s.parse())
+                .transpose()
+                .map_err(|e| ConfigError::InvalidValue {
+                    key: "MAX_COST_PER_DAY_CENTS".to_string(),
+                    message: format!("must be a positive integer: {e}"),
+                })?,
+            max_actions_per_hour: optional_env("MAX_ACTIONS_PER_HOUR")?
+                .map(|s| s.parse())
+                .transpose()
+                .map_err(|e| ConfigError::InvalidValue {
+                    key: "MAX_ACTIONS_PER_HOUR".to_string(),
+                    message: format!("must be a positive integer: {e}"),
+                })?,
+            max_tool_iterations: optional_env("AGENT_MAX_TOOL_ITERATIONS")?
+                .map(|s| s.parse())
+                .transpose()
+                .map_err(|e| ConfigError::InvalidValue {
+                    key: "AGENT_MAX_TOOL_ITERATIONS".to_string(),
+                    message: format!("must be a positive integer: {e}"),
+                })?
+                .unwrap_or(settings.agent.max_tool_iterations),
+            auto_approve_tools: optional_env("AGENT_AUTO_APPROVE_TOOLS")?
+                .map(|s| s.parse())
+                .transpose()
+                .map_err(|e| ConfigError::InvalidValue {
+                    key: "AGENT_AUTO_APPROVE_TOOLS".to_string(),
+                    message: format!("must be 'true' or 'false': {e}"),
+                })?
+                .unwrap_or(settings.agent.auto_approve_tools),
+        })
+    }
+}

src/config/builder.rs

@@ -0,0 +1,72 @@
+use std::path::PathBuf;
+use std::time::Duration;
+
+use crate::config::helpers::{optional_env, parse_optional_env};
+use crate::error::ConfigError;
+
+/// Builder mode configuration.
+#[derive(Debug, Clone)]
+pub struct BuilderModeConfig {
+    /// Whether the software builder tool is enabled.
+    pub enabled: bool,
+    /// Directory for build artifacts (default: temp dir).
+    pub build_dir: Option<PathBuf>,
+    /// Maximum iterations for the build loop.
+    pub max_iterations: u32,
+    /// Build timeout in seconds.
+    pub timeout_secs: u64,
+    /// Whether to automatically register built WASM tools.
+    pub auto_register: bool,
+}
+
+impl Default for BuilderModeConfig {
+    fn default() -> Self {
+        Self {
+            enabled: true,
+            build_dir: None,
+            max_iterations: 20,
+            timeout_secs: 600,
+            auto_register: true,
+        }
+    }
+}
+
+impl BuilderModeConfig {
+    pub(crate) fn resolve() -> Result<Self, ConfigError> {
+        Ok(Self {
+            enabled: optional_env("BUILDER_ENABLED")?
+                .map(|s| s.parse())
+                .transpose()
+                .map_err(|e| ConfigError::InvalidValue {
+                    key: "BUILDER_ENABLED".to_string(),
+                    message: format!("must be 'true' or 'false': {e}"),
+                })?
+                .unwrap_or(true),
+            build_dir: optional_env("BUILDER_DIR")?.map(PathBuf::from),
+            max_iterations: parse_optional_env("BUILDER_MAX_ITERATIONS", 20)?,
+            timeout_secs: parse_optional_env("BUILDER_TIMEOUT_SECS", 600)?,
+            auto_register: optional_env("BUILDER_AUTO_REGISTER")?
+                .map(|s| s.parse())
+                .transpose()
+                .map_err(|e| ConfigError::InvalidValue {
+                    key: "BUILDER_AUTO_REGISTER".to_string(),
+                    message: format!("must be 'true' or 'false': {e}"),
+                })?
+                .unwrap_or(true),
+        })
+    }
+
+    /// Convert to BuilderConfig for the builder tool.
+    pub fn to_builder_config(&self) -> crate::tools::BuilderConfig {
+        crate::tools::BuilderConfig {
+            build_dir: self.build_dir.clone().unwrap_or_else(std::env::temp_dir),
+            max_iterations: self.max_iterations,
+            timeout: Duration::from_secs(self.timeout_secs),
+            cleanup_on_failure: true,
+            validate_wasm: true,
+            run_tests: true,
+            auto_register: self.auto_register,
+            wasm_output_dir: None,
+        }
+    }
+}

src/config/channels.rs

@@ -0,0 +1,126 @@
+use std::path::PathBuf;
+
+use secrecy::SecretString;
+
+use crate::config::helpers::optional_env;
+use crate::error::ConfigError;
+use crate::settings::Settings;
+
+/// Channel configurations.
+#[derive(Debug, Clone)]
+pub struct ChannelsConfig {
+    pub cli: CliConfig,
+    pub http: Option<HttpConfig>,
+    pub gateway: Option<GatewayConfig>,
+    /// Directory containing WASM channel modules (default: ~/.ironclaw/channels/).
+    pub wasm_channels_dir: std::path::PathBuf,
+    /// Whether WASM channels are enabled.
+    pub wasm_channels_enabled: bool,
+    /// Telegram owner user ID. When set, the bot only responds to this user.
+    pub telegram_owner_id: Option<i64>,
+}
+
+#[derive(Debug, Clone)]
+pub struct CliConfig {
+    pub enabled: bool,
+}
+
+#[derive(Debug, Clone)]
+pub struct HttpConfig {
+    pub host: String,
+    pub port: u16,
+    pub webhook_secret: Option<SecretString>,
+    pub user_id: String,
+}
+
+/// Web gateway configuration.
+#[derive(Debug, Clone)]
+pub struct GatewayConfig {
+    pub host: String,
+    pub port: u16,
+    /// Bearer token for authentication. Random hex generated at startup if unset.
+    pub auth_token: Option<String>,
+    pub user_id: String,
+}
+
+impl ChannelsConfig {
+    pub(crate) fn resolve(settings: &Settings) -> Result<Self, ConfigError> {
+        let http = if optional_env("HTTP_PORT")?.is_some() || optional_env("HTTP_HOST")?.is_some() {
+            Some(HttpConfig {
+                host: optional_env("HTTP_HOST")?.unwrap_or_else(|| "0.0.0.0".to_string()),
+                port: optional_env("HTTP_PORT")?
+                    .map(|s| s.parse())
+                    .transpose()
+                    .map_err(|e| ConfigError::InvalidValue {
+                        key: "HTTP_PORT".to_string(),
+                        message: format!("must be a valid port number: {e}"),
+                    })?
+                    .unwrap_or(8080),
+                webhook_secret: optional_env("HTTP_WEBHOOK_SECRET")?.map(SecretString::from),
+                user_id: optional_env("HTTP_USER_ID")?.unwrap_or_else(|| "http".to_string()),
+            })
+        } else {
+            None
+        };
+
+        let gateway = if optional_env("GATEWAY_ENABLED")?
+            .map(|s| s.to_lowercase() == "true" || s == "1")
+            .unwrap_or(true)
+        {
+            Some(GatewayConfig {
+                host: optional_env("GATEWAY_HOST")?.unwrap_or_else(|| "127.0.0.1".to_string()),
+                port: optional_env("GATEWAY_PORT")?
+                    .map(|s| s.parse())
+                    .transpose()
+                    .map_err(|e| ConfigError::InvalidValue {
+                        key: "GATEWAY_PORT".to_string(),
+                        message: format!("must be a valid port number: {e}"),
+                    })?
+                    .unwrap_or(3000),
+                auth_token: optional_env("GATEWAY_AUTH_TOKEN")?,
+                user_id: optional_env("GATEWAY_USER_ID")?.unwrap_or_else(|| "default".to_string()),
+            })
+        } else {
+            None
+        };
+
+        let cli_enabled = optional_env("CLI_ENABLED")?
+            .map(|s| s.to_lowercase() != "false" && s != "0")
+            .unwrap_or(true);
+
+        Ok(Self {
+            cli: CliConfig {
+                enabled: cli_enabled,
+            },
+            http,
+            gateway,
+            wasm_channels_dir: optional_env("WASM_CHANNELS_DIR")?
+                .map(PathBuf::from)
+                .unwrap_or_else(default_channels_dir),
+            wasm_channels_enabled: optional_env("WASM_CHANNELS_ENABLED")?
+                .map(|s| s.parse())
+                .transpose()
+                .map_err(|e| ConfigError::InvalidValue {
+                    key: "WASM_CHANNELS_ENABLED".to_string(),
+                    message: format!("must be 'true' or 'false': {e}"),
+                })?
+                .unwrap_or(true),
+            telegram_owner_id: optional_env("TELEGRAM_OWNER_ID")?
+                .map(|s| s.parse())
+                .transpose()
+                .map_err(|e| ConfigError::InvalidValue {
+                    key: "TELEGRAM_OWNER_ID".to_string(),
+                    message: format!("must be an integer: {e}"),
+                })?
+                .or(settings.channels.telegram_owner_id),
+        })
+    }
+}
+
+/// Get the default channels directory (~/.ironclaw/channels/).
+fn default_channels_dir() -> PathBuf {
+    dirs::home_dir()
+        .unwrap_or_else(|| PathBuf::from("."))
+        .join(".ironclaw")
+        .join("channels")
+}

src/config/database.rs

@@ -0,0 +1,130 @@
+use std::path::PathBuf;
+
+use secrecy::{ExposeSecret, SecretString};
+
+use crate::config::helpers::{optional_env, parse_optional_env};
+use crate::error::ConfigError;
+
+/// Which database backend to use.
+#[derive(Debug, Clone, Copy, PartialEq, Eq, Default)]
+pub enum DatabaseBackend {
+    /// PostgreSQL via deadpool-postgres (default).
+    #[default]
+    Postgres,
+    /// libSQL/Turso embedded database.
+    LibSql,
+}
+
+impl std::fmt::Display for DatabaseBackend {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        match self {
+            Self::Postgres => write!(f, "postgres"),
+            Self::LibSql => write!(f, "libsql"),
+        }
+    }
+}
+
+impl std::str::FromStr for DatabaseBackend {
+    type Err = String;
+
+    fn from_str(s: &str) -> Result<Self, Self::Err> {
+        match s.to_lowercase().as_str() {
+            "postgres" | "postgresql" | "pg" => Ok(Self::Postgres),
+            "libsql" | "turso" | "sqlite" => Ok(Self::LibSql),
+            _ => Err(format!(
+                "invalid database backend '{}', expected 'postgres' or 'libsql'",
+                s
+            )),
+        }
+    }
+}
+
+/// Database configuration.
+#[derive(Debug, Clone)]
+pub struct DatabaseConfig {
+    /// Which backend to use (default: Postgres).
+    pub backend: DatabaseBackend,
+
+    // -- PostgreSQL fields --
+    pub url: SecretString,
+    pub pool_size: usize,
+
+    // -- libSQL fields --
+    /// Path to local libSQL database file (default: ~/.ironclaw/ironclaw.db).
+    pub libsql_path: Option<PathBuf>,
+    /// Turso cloud URL for remote sync (optional).
+    pub libsql_url: Option<String>,
+    /// Turso auth token (required when libsql_url is set).
+    pub libsql_auth_token: Option<SecretString>,
+}
+
+impl DatabaseConfig {
+    pub(crate) fn resolve() -> Result<Self, ConfigError> {
+        let backend: DatabaseBackend = if let Some(b) = optional_env("DATABASE_BACKEND")? {
+            b.parse().map_err(|e| ConfigError::InvalidValue {
+                key: "DATABASE_BACKEND".to_string(),
+                message: e,
+            })?
+        } else {
+            DatabaseBackend::default()
+        };
+
+        // PostgreSQL URL is required only when using the postgres backend.
+        // For libsql backend, default to an empty placeholder.
+        // DATABASE_URL is loaded from ~/.ironclaw/.env via dotenvy early in startup.
+        let url = optional_env("DATABASE_URL")?
+            .or_else(|| {
+                if backend == DatabaseBackend::LibSql {
+                    Some("unused://libsql".to_string())
+                } else {
+                    None
+                }
+            })
+            .ok_or_else(|| ConfigError::MissingRequired {
+                key: "DATABASE_URL".to_string(),
+                hint: "Run 'ironclaw onboard' or set DATABASE_URL environment variable".to_string(),
+            })?;
+
+        let pool_size = parse_optional_env("DATABASE_POOL_SIZE", 10)?;
+
+        let libsql_path = optional_env("LIBSQL_PATH")?.map(PathBuf::from).or_else(|| {
+            if backend == DatabaseBackend::LibSql {
+                Some(default_libsql_path())
+            } else {
+                None
+            }
+        });
+
+        let libsql_url = optional_env("LIBSQL_URL")?;
+        let libsql_auth_token = optional_env("LIBSQL_AUTH_TOKEN")?.map(SecretString::from);
+
+        if libsql_url.is_some() && libsql_auth_token.is_none() {
+            return Err(ConfigError::MissingRequired {
+                key: "LIBSQL_AUTH_TOKEN".to_string(),
+                hint: "LIBSQL_AUTH_TOKEN is required when LIBSQL_URL is set".to_string(),
+            });
+        }
+
+        Ok(Self {
+            backend,
+            url: SecretString::from(url),
+            pool_size,
+            libsql_path,
+            libsql_url,
+            libsql_auth_token,
+        })
+    }
+
+    /// Get the database URL (exposes the secret).
+    pub fn url(&self) -> &str {
+        self.url.expose_secret()
+    }
+}
+
+/// Default libSQL database path (~/.ironclaw/ironclaw.db).
+pub fn default_libsql_path() -> PathBuf {
+    dirs::home_dir()
+        .unwrap_or_else(|| PathBuf::from("."))
+        .join(".ironclaw")
+        .join("ironclaw.db")
+}

src/config/embeddings.rs

@@ -0,0 +1,199 @@
+use secrecy::{ExposeSecret, SecretString};
+
+use crate::config::helpers::optional_env;
+use crate::error::ConfigError;
+use crate::settings::Settings;
+
+/// Embeddings provider configuration.
+#[derive(Debug, Clone)]
+pub struct EmbeddingsConfig {
+    /// Whether embeddings are enabled.
+    pub enabled: bool,
+    /// Provider to use: "openai", "nearai", or "ollama"
+    pub provider: String,
+    /// OpenAI API key (for OpenAI provider).
+    pub openai_api_key: Option<SecretString>,
+    /// Model to use for embeddings.
+    pub model: String,
+    /// Ollama base URL (for Ollama provider). Defaults to http://localhost:11434.
+    pub ollama_base_url: String,
+    /// Embedding vector dimension. Inferred from the model name when not set explicitly.
+    pub dimension: usize,
+}
+
+impl Default for EmbeddingsConfig {
+    fn default() -> Self {
+        let model = "text-embedding-3-small".to_string();
+        let dimension = default_dimension_for_model(&model);
+        Self {
+            enabled: false,
+            provider: "openai".to_string(),
+            openai_api_key: None,
+            model,
+            ollama_base_url: "http://localhost:11434".to_string(),
+            dimension,
+        }
+    }
+}
+
+/// Infer the embedding dimension from a well-known model name.
+///
+/// Falls back to 1536 (OpenAI text-embedding-3-small default) for unknown models.
+fn default_dimension_for_model(model: &str) -> usize {
+    match model {
+        "text-embedding-3-small" => 1536,
+        "text-embedding-3-large" => 3072,
+        "text-embedding-ada-002" => 1536,
+        "nomic-embed-text" => 768,
+        "mxbai-embed-large" => 1024,
+        "all-minilm" => 384,
+        _ => 1536,
+    }
+}
+
+impl EmbeddingsConfig {
+    pub(crate) fn resolve(settings: &Settings) -> Result<Self, ConfigError> {
+        let openai_api_key = optional_env("OPENAI_API_KEY")?.map(SecretString::from);
+
+        let provider = optional_env("EMBEDDING_PROVIDER")?
+            .unwrap_or_else(|| settings.embeddings.provider.clone());
+
+        let model =
+            optional_env("EMBEDDING_MODEL")?.unwrap_or_else(|| settings.embeddings.model.clone());
+
+        let ollama_base_url = optional_env("OLLAMA_BASE_URL")?
+            .or_else(|| settings.ollama_base_url.clone())
+            .unwrap_or_else(|| "http://localhost:11434".to_string());
+
+        let dimension = optional_env("EMBEDDING_DIMENSION")?
+            .map(|s| s.parse::<usize>())
+            .transpose()
+            .map_err(|e| ConfigError::InvalidValue {
+                key: "EMBEDDING_DIMENSION".to_string(),
+                message: format!("must be a positive integer: {e}"),
+            })?
+            .unwrap_or_else(|| default_dimension_for_model(&model));
+
+        let enabled = optional_env("EMBEDDING_ENABLED")?
+            .map(|s| s.parse())
+            .transpose()
+            .map_err(|e| ConfigError::InvalidValue {
+                key: "EMBEDDING_ENABLED".to_string(),
+                message: format!("must be 'true' or 'false': {e}"),
+            })?
+            .unwrap_or(settings.embeddings.enabled);
+
+        Ok(Self {
+            enabled,
+            provider,
+            openai_api_key,
+            model,
+            ollama_base_url,
+            dimension,
+        })
+    }
+
+    /// Get the OpenAI API key if configured.
+    pub fn openai_api_key(&self) -> Option<&str> {
+        self.openai_api_key.as_ref().map(|s| s.expose_secret())
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use crate::config::helpers::ENV_MUTEX;
+    use crate::settings::{EmbeddingsSettings, Settings};
+
+    /// Clear all embedding-related env vars.
+    fn clear_embedding_env() {
+        // SAFETY: Only called under ENV_MUTEX in tests.
+        unsafe {
+            std::env::remove_var("EMBEDDING_ENABLED");
+            std::env::remove_var("EMBEDDING_PROVIDER");
+            std::env::remove_var("EMBEDDING_MODEL");
+            std::env::remove_var("OPENAI_API_KEY");
+        }
+    }
+
+    #[test]
+    fn embeddings_disabled_not_overridden_by_openai_key() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+
+        clear_embedding_env();
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe {
+            std::env::set_var("OPENAI_API_KEY", "sk-test-key-for-issue-129");
+        }
+
+        let settings = Settings {
+            embeddings: EmbeddingsSettings {
+                enabled: false,
+                ..Default::default()
+            },
+            ..Default::default()
+        };
+
+        let config = EmbeddingsConfig::resolve(&settings).expect("resolve should succeed");
+        assert!(
+            !config.enabled,
+            "embeddings should remain disabled when settings.embeddings.enabled=false, \
+             even when OPENAI_API_KEY is set (issue #129)"
+        );
+
+        // SAFETY: Under ENV_MUTEX.
+        unsafe {
+            std::env::remove_var("OPENAI_API_KEY");
+        }
+    }
+
+    #[test]
+    fn embeddings_enabled_from_settings() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        clear_embedding_env();
+
+        let settings = Settings {
+            embeddings: EmbeddingsSettings {
+                enabled: true,
+                ..Default::default()
+            },
+            ..Default::default()
+        };
+
+        let config = EmbeddingsConfig::resolve(&settings).expect("resolve should succeed");
+        assert!(
+            config.enabled,
+            "embeddings should be enabled when settings say so"
+        );
+    }
+
+    #[test]
+    fn embeddings_env_override_takes_precedence() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+
+        clear_embedding_env();
+        // SAFETY: Under ENV_MUTEX.
+        unsafe {
+            std::env::set_var("EMBEDDING_ENABLED", "true");
+        }
+
+        let settings = Settings {
+            embeddings: EmbeddingsSettings {
+                enabled: false,
+                ..Default::default()
+            },
+            ..Default::default()
+        };
+
+        let config = EmbeddingsConfig::resolve(&settings).expect("resolve should succeed");
+        assert!(
+            config.enabled,
+            "EMBEDDING_ENABLED=true env var should override settings"
+        );
+
+        // SAFETY: Under ENV_MUTEX.
+        unsafe {
+            std::env::remove_var("EMBEDDING_ENABLED");
+        }
+    }
+}

src/config/heartbeat.rs

@@ -0,0 +1,54 @@
+use crate::config::helpers::optional_env;
+use crate::error::ConfigError;
+use crate::settings::Settings;
+
+/// Heartbeat configuration.
+#[derive(Debug, Clone)]
+pub struct HeartbeatConfig {
+    /// Whether heartbeat is enabled.
+    pub enabled: bool,
+    /// Interval between heartbeat checks in seconds.
+    pub interval_secs: u64,
+    /// Channel to notify on heartbeat findings.
+    pub notify_channel: Option<String>,
+    /// User ID to notify on heartbeat findings.
+    pub notify_user: Option<String>,
+}
+
+impl Default for HeartbeatConfig {
+    fn default() -> Self {
+        Self {
+            enabled: false,
+            interval_secs: 1800, // 30 minutes
+            notify_channel: None,
+            notify_user: None,
+        }
+    }
+}
+
+impl HeartbeatConfig {
+    pub(crate) fn resolve(settings: &Settings) -> Result<Self, ConfigError> {
+        Ok(Self {
+            enabled: optional_env("HEARTBEAT_ENABLED")?
+                .map(|s| s.parse())
+                .transpose()
+                .map_err(|e| ConfigError::InvalidValue {
+                    key: "HEARTBEAT_ENABLED".to_string(),
+                    message: format!("must be 'true' or 'false': {e}"),
+                })?
+                .unwrap_or(settings.heartbeat.enabled),
+            interval_secs: optional_env("HEARTBEAT_INTERVAL_SECS")?
+                .map(|s| s.parse())
+                .transpose()
+                .map_err(|e| ConfigError::InvalidValue {
+                    key: "HEARTBEAT_INTERVAL_SECS".to_string(),
+                    message: format!("must be a positive integer: {e}"),
+                })?
+                .unwrap_or(settings.heartbeat.interval_secs),
+            notify_channel: optional_env("HEARTBEAT_NOTIFY_CHANNEL")?
+                .or_else(|| settings.heartbeat.notify_channel.clone()),
+            notify_user: optional_env("HEARTBEAT_NOTIFY_USER")?
+                .or_else(|| settings.heartbeat.notify_user.clone()),
+        })
+    }
+}