fix: review fixes for libSQL backend (shared connections, panics, indexes)

- Replace .expect() with proper error propagation in 3 call sites
- Share Arc<Database> between backend and stores instead of single Connection
- Add connect-per-operation pattern to LibSqlSecretsStore and LibSqlWasmToolStore
- Wrap store() INSERT + SELECT-back in a transaction
- Add ~22 missing indexes for parity with PostgreSQL schema
- Add 18 leak_detection_patterns seed rows matching PostgreSQL V2 migration
- Fix super:: import to use crate:: style
- Gate mask_password_in_url behind #[cfg(feature = "postgres")]
- Rewrite secrets store init with or_else chain for runtime backend selection

Co-Authored-By: Claude Opus 4.6 <[email protected]>

.claude/commands/fix-issue.md

@@ -1,97 +0,0 @@
----
-description: Fetch a GitHub issue, create a branch, research the codebase, plan the fix, implement with tests, and commit
-disable-model-invocation: true
-allowed-tools: Bash(gh issue view:*), Bash(gh repo view:*), Bash(git fetch:*), Bash(git checkout:*), Bash(git status:*), Bash(git branch:*), Bash(git add:*), Bash(git commit:*), Bash(cargo fmt:*), Bash(cargo clippy:*), Bash(cargo test:*), Read, Edit, Write, Grep, Glob
-argument-hint: "<issue-number or github-issue-url>"
----
-
-# Fix GitHub Issue
-
-## Step 1: Resolve the issue
-
-Parse `$ARGUMENTS` to extract the issue number:
-- If it's a URL like `https://github.com/owner/repo/issues/42`, extract `42`.
-- If it's a bare number, use it directly.
-- If empty, stop and ask the user for an issue number.
-
-Fetch the issue:
-
-```
-gh issue view {number} --json title,body,labels,assignees,comments,state
-```
-
-If the issue is closed, warn the user and ask if they still want to proceed.
-
-## Step 2: Create a branch
-
-Create a fresh branch off the latest main:
-
-1. Fetch latest: `git fetch origin`
-2. Detect default branch: `gh repo view --json defaultBranchRef --jq .defaultBranchRef.name`
-3. Create and switch to a new branch: `git checkout -b fix/{number}-{short-slug} origin/{default-branch}`
-   - `{short-slug}` is 3-5 words from the issue title, lowercase, hyphenated (e.g. `fix/42-idor-workspace-check`)
-
-If the working tree has uncommitted changes, warn the user and stop. Do not stash or discard their work.
-
-## Step 3: Understand the issue
-
-Summarize the issue in 2-3 sentences. Identify:
-- **What's broken or missing** (the symptom or feature request)
-- **Acceptance criteria** (what "done" looks like, from the issue body or comments)
-- **Constraints** (mentioned technologies, backward compatibility, performance requirements)
-
-If the issue is unclear or ambiguous, list the open questions. These will be addressed during planning.
-
-## Step 4: Research the codebase
-
-Before planning, gather context:
-
-1. **Find relevant code** - Search for files, functions, types, and patterns mentioned in the issue. Read them in full.
-2. **Trace the flow** - If the issue is about a specific behavior, trace the code path from the entry point (route handler, CLI command, etc.) through to the relevant logic.
-3. **Check existing tests** - Find tests related to the affected code. Understand what's already covered.
-4. **Check for prior art** - Look for similar patterns in the codebase that solve analogous problems. Prefer consistency with existing patterns.
-
-## Step 5: Enter planning mode
-
-Enter planning mode to design the implementation. The plan MUST cover:
-
-1. **Root cause** (for bugs) or **design approach** (for features)
-2. **Files to modify** with specific descriptions of what changes in each
-3. **New files** (if any) with justification for why they're needed
-4. **Tests to add** - every code path introduced or changed needs a test:
-   - Happy path (expected input produces expected output)
-   - Error paths (invalid input, missing data, permission denied)
-   - Edge cases (empty collections, boundary values, concurrent access)
-5. **IronClaw-specific concerns**:
-   - If the change touches persistence, both database backends must be updated (`postgres.rs` and `libsql_backend.rs`)
-   - New `Database` trait methods need implementations in both backends
-   - No `.unwrap()` or `.expect()` in production code
-   - Use `crate::` imports, not `super::`
-   - Error types via `thiserror` in `error.rs`
-6. **Migration or compatibility concerns** (if any)
-
-Follow the project's CLAUDE.md guidance for architecture decisions.
-
-Wait for user approval before implementing.
-
-## Step 6: Implement
-
-After the plan is approved:
-
-1. Implement each change from the plan.
-2. Write all planned tests.
-3. Run IronClaw's full quality gate:
-   - `cargo fmt`
-   - `cargo clippy --all --benches --tests --examples --all-features` (zero warnings)
-   - `cargo test --lib` (all tests pass)
-4. If any check fails, fix it before proceeding.
-
-Note: Integration tests (`--test workspace_integration`) require PostgreSQL and are expected to fail locally. Only `--lib` test failures are blocking.
-
-## Step 7: Commit and summarize
-
-1. Commit with a descriptive message referencing the issue (e.g. `fix: prevent IDOR in function call outputs (#42)`).
-2. Summarize what was done:
-   - Files changed with line references
-   - Tests added and what they cover
-   - Any follow-up work or open questions

.claude/commands/respond-pr.md

@@ -1,81 +0,0 @@
----
-description: Respond to PR review comments — triage, plan fixes, implement after confirmation, push, and reply to reviewers
-disable-model-invocation: true
-allowed-tools: Bash(gh pr list:*), Bash(gh pr comment:*), Bash(gh api:*), Bash(gh repo view:*), Bash(git branch:*), Bash(git status:*), Bash(git add:*), Bash(git commit:*), Bash(git push:*), Bash(cargo fmt:*), Bash(cargo clippy:*), Bash(cargo test:*), Read, Edit, Write, Grep, Glob
-argument-hint: "[pr-number (optional, auto-detects from branch)]"
----
-
-# Review and Address PR Comments
-
-## Step 1: Find the PR
-
-If `$ARGUMENTS` is provided, use that as the PR number. Otherwise, detect the PR for the current branch:
-
-```
-gh pr list --head $(git branch --show-current) --json number,title,url --jq '.[0]'
-```
-
-If no PR is found, tell the user and stop.
-
-## Step 2: Fetch all review comments
-
-Resolve the repo owner and name:
-
-```
-gh repo view --json owner,name --jq '"\(.owner.login)/\(.name)"'
-```
-
-Fetch the full set of review comments (not issue-level comments):
-
-```
-gh api --paginate repos/{owner}/{repo}/pulls/{number}/comments
-```
-
-Also fetch the review summaries:
-
-```
-gh api --paginate repos/{owner}/{repo}/pulls/{number}/reviews
-```
-
-Deduplicate comments that appear multiple times (bots sometimes post the same finding under different IDs). Group by the actual issue being raised, not by comment ID.
-
-## Step 3: Triage and plan
-
-For each unique issue raised in the comments:
-
-1. **Check if already addressed** - Read the current code at the referenced location. If a prior commit already fixed it, note it as "already resolved".
-2. **Assess validity** - Determine if the comment identifies a real problem or is a false positive. Be honest about false positives but explain why.
-3. **Classify severity** - Critical (security/data loss), High (bugs/broken behavior), Medium (correctness/robustness), Low (style/naming/nits).
-4. **Plan the fix** - For each valid unresolved issue, describe the specific code change needed.
-
-Present the plan as a table to the user:
-
-| # | Issue | File:Line | Severity | Status | Planned Fix |
-|---|-------|-----------|----------|--------|-------------|
-
-Wait for user confirmation before proceeding to implementation.
-
-## Step 4: Implement fixes
-
-After user confirms:
-
-1. Implement each fix in the plan.
-2. Run IronClaw's quality gate to verify nothing breaks:
-   - `cargo fmt`
-   - `cargo clippy --all --benches --tests --examples --all-features`
-   - `cargo test --lib`
-3. Commit with a descriptive message referencing the PR review.
-4. Push to the branch.
-
-## Step 5: Reply to comments
-
-For each comment addressed, reply on the PR with a short message stating what was fixed and the commit SHA. For false positives or already-resolved items, reply explaining why no change was needed.
-
-## Rules
-
-- Never guess at code you haven't read. Always read the referenced file and line before assessing a comment.
-- Group duplicate comments (same issue reported by multiple bots) and reply to all of them.
-- Do not make changes beyond what the review comments ask for. Stay focused.
-- If a comment suggests a change you disagree with, present your reasoning to the user during the planning phase rather than silently ignoring it.
-- Follow IronClaw conventions: no `.unwrap()` in production code, use `crate::` imports, `thiserror` errors.
-- If changes touch persistence, verify both database backends are updated.

.claude/commands/review-crate.md

@@ -1,245 +0,0 @@
----
-description: Deep audit of the IronClaw crate for vulnerabilities, bugs, unfinished work, inconsistencies, and oversights
-disable-model-invocation: true
-allowed-tools: Bash(cargo fmt:*), Bash(cargo clippy:*), Bash(cargo test:*), Bash(cargo audit:*), Bash(git diff:*), Bash(git log:*), Bash(git show:*), Bash(wc:*), Read, Grep, Glob, Task
-argument-hint: "[path/to/crate]"
----
-
-# Rust Crate Audit
-
-You are performing a thorough audit of a Rust crate. Your goal is to find every vulnerability, bug, unfinished piece of work, inconsistency, and oversight before it ships. Leave no stone unturned.
-
-## Step 1: Locate the crate
-
-Parse `$ARGUMENTS`:
-- If a path is provided, use it as the crate root.
-- If empty, use the current working directory.
-
-Verify it's a valid Rust crate by checking for `Cargo.toml`. If not found, stop and ask the user.
-
-## Step 2: Understand the crate
-
-Read `Cargo.toml` to understand:
-- Crate name, version, edition
-- Dependencies (look for outdated, unmaintained, or suspicious crates)
-- Feature flags and their implications
-- Build scripts (`build.rs`) if any
-
-Read `CLAUDE.md`, `README.md`, or top-level documentation if present to understand intent and architecture.
-
-Read `src/lib.rs` or `src/main.rs` to get the module tree. Then read each module's `mod.rs` or top-level file to build a mental map of the crate's structure before diving into details.
-Read all Rust files (`src/*.rs`) to make sure everything is in context when you are reasoning.
-
-## Step 3: Run the compiler's checks
-
-Run these commands and capture output. Do NOT fix anything, just collect findings:
-
-```
-cargo fmt --check 2>&1
-```
-
-```
-cargo clippy --all --benches --tests --examples --all-features -- -W clippy::all -W clippy::pedantic -W clippy::nursery 2>&1
-```
-
-```
-cargo test --lib 2>&1
-```
-
-If any of these fail, record the failures as findings. If `cargo test` has ignored tests, note which ones and why.
-
-Note: Integration tests (`--test workspace_integration`) require a PostgreSQL database and are expected to fail locally. Only report `--lib` test failures as blocking.
-
-## Step 4: Scan for unfinished work
-
-Search the entire `src/` tree for:
-
-```
-todo!
-unimplemented!
-fixme
-FIXME
-TODO
-HACK
-XXX
-SAFETY:
-stub
-placeholder
-temporary
-```
-
-For each match:
-- Is it in production code or test code?
-- Is it a genuine incomplete feature or a deliberate placeholder?
-- Is there a tracking issue referenced?
-- Could this panic at runtime?
-
-Any `todo!()` or `unimplemented!()` in non-test code is **High severity** (runtime panic).
-
-## Step 5: Audit for vulnerabilities and unsafe code
-
-### 5a. Unsafe code
-
-Search for all `unsafe` blocks. For each one:
-- Is the safety invariant documented with a `// SAFETY:` comment?
-- Is the invariant actually upheld by the surrounding code?
-- Could the unsafe block be replaced with a safe alternative?
-- Are there any pointer dereferences, transmutes, or FFI calls?
-
-### 5b. Unwrap and panic paths
-
-Search for `.unwrap()`, `.expect(`, `panic!`, `unreachable!` in non-test code. For each:
-- Can this actually panic in production?
-- Is there a code path that reaches this with None/Err?
-- Should it be replaced with proper error handling (`?`, `.ok()`, `.unwrap_or_default()`)?
-
-IronClaw convention: `.unwrap()` and `.expect()` are banned in production code. Any occurrence outside `#[cfg(test)]` blocks is a **High severity** finding.
-
-### 5c. SQL and injection vectors
-
-Search for string formatting used in SQL queries, shell commands, or HTML:
-- `format!` used near `.execute(`, `.query(`, `Command::new(`
-- String interpolation in query construction vs parameterized queries
-- User input flowing into file paths (`Path::new`, `std::fs::`)
-
-IronClaw has two database backends (PostgreSQL and libSQL). Check both for injection vectors.
-
-### 5d. Cryptographic issues
-
-If the crate uses crypto:
-- Are comparisons constant-time? (look for `==` on secrets/hashes vs `subtle::ConstantTimeEq`)
-- Is randomness from `OsRng` / `thread_rng` and not a fixed seed?
-- Are keys/secrets zeroized after use? (`secrecy`, `zeroize` crates)
-- Are deprecated algorithms used? (MD5, SHA1 for security, RC4, DES)
-
-### 5e. Resource exhaustion
-
-- Are there unbounded allocations? (`Vec` growing from user input without limits)
-- Are there unbounded loops? (retry loops without max attempts)
-- Are file reads bounded? (`std::fs::read_to_string` on user-provided paths)
-- Are timeouts set on all network operations?
-- Are there connection/resource leaks? (opened but never closed, missing `Drop`)
-
-### 5f. Error handling
-
-- Are errors swallowed silently? (`let _ = ...`, `.ok()` discarding errors that matter)
-- Do error types carry enough context to debug in production?
-- Are there error type mismatches? (returning generic `anyhow::Error` where a typed error would prevent confusion)
-- Is `thiserror` used consistently for error types (IronClaw convention)?
-
-## Step 6: Check for inconsistencies
-
-### 6a. Naming conventions
-
-- Are types, functions, modules named consistently? (e.g., mixing `get_` and `fetch_`, `create_` and `new_`)
-- Do similar operations follow the same patterns?
-
-### 6b. Duplicate or near-duplicate code
-
-Look for:
-- Functions that do nearly the same thing with minor variations (candidates for generics or shared helpers)
-- Repeated error mapping patterns that should be extracted
-- Copy-pasted SQL queries or string templates with slight differences
-- Identical struct definitions or conversion logic in different modules
-
-### 6c. API consistency
-
-- Do similar functions take arguments in the same order?
-- Are return types consistent? (e.g., some functions return `Option<T>`, similar ones return `Result<T, E>`)
-- Are visibility modifiers consistent? (`pub` where it should be `pub(crate)`, or vice versa)
-
-### 6d. Dead code and unused items
-
-- Are there functions, structs, or modules that nothing references?
-- Are there `#[allow(dead_code)]` annotations that should be investigated?
-- Are there feature-gated items where the feature is never enabled?
-
-### 6e. Import style
-
-IronClaw convention: use `crate::` imports, not `super::`. Flag any `super::` imports in non-test code.
-
-## Step 7: Inspect for change oversights
-
-### 7a. Partial refactors
-
-- Are there old patterns coexisting with new patterns?
-- Are there renamed types/functions where some call sites still use the old name via a compatibility alias?
-- Are there comments referencing behavior that no longer exists?
-
-### 7b. Trait implementation gaps
-
-- If a trait is defined, do all intended types implement it?
-- Are there `impl` blocks that look incomplete?
-- Are `Default` implementations sensible?
-
-IronClaw key traits: `Database` (~60 methods), `Channel`, `Tool`, `LlmProvider`, `SuccessEvaluator`, `EmbeddingProvider`. If any new methods were added to `Database`, verify both `postgres.rs` and `libsql_backend.rs` implement them.
-
-### 7c. Test coverage gaps
-
-- Are there public functions without any test?
-- Are there error paths without tests?
-- Are there recently-changed functions where the tests still assert old behavior?
-
-### 7d. Documentation drift
-
-- Do doc comments match actual function behavior?
-- Are examples in doc comments still valid and compilable?
-
-## Step 8: Dependency audit
-
-Review `Cargo.toml` and `Cargo.lock`:
-- Are there duplicate versions of the same crate in the lock file? (potential version conflicts)
-- Are there dependencies with known security advisories? Run `cargo audit` to check (install with `cargo install cargo-audit` if not present).
-- Are there heavy dependencies used for trivial functionality?
-- Are dependency features minimal?
-
-## Step 9: Present findings
-
-Compile all findings into a structured report. Group by severity, then by category.
-
-### Format
-
-For each finding:
-
-```
-### [Severity] Category: One-line summary
-
-**Location:** `file_path:line_number`
-**Category:** Vulnerability | Bug | Unfinished | Inconsistency | Duplicate | Oversight | Style
-
-**Description:**
-Detailed explanation of the issue, why it matters, and how it could manifest.
-
-**Suggested fix:**
-Concrete suggestion with code if applicable.
-```
-
-### Severity levels
-
-- **Critical**: Security vulnerability, data loss, or crash in production
-- **High**: Bug that causes incorrect behavior, `todo!()`/`unimplemented!()` in prod code, or missing validation on trust boundaries
-- **Medium**: Inconsistency, duplicate code, incomplete error handling, missing tests for important paths
-- **Low**: Naming inconsistency, unnecessary complexity, documentation drift, minor dead code
-- **Nit**: Style preference, optional improvement
-
-### Summary table
-
-End with a summary table:
-
-| # | Severity | Category | File:Line | Finding |
-|---|----------|----------|-----------|---------|
-
-And a final tally: X Critical, Y High, Z Medium, W Low, V Nit.
-
-## Rules
-
-- Read every file before reporting on it. Never guess about code you haven't seen.
-- Be specific. "This might have issues" is worthless. "Line 42 calls `.unwrap()` on a `Result` that returns `Err` when the DB connection is dropped" is useful.
-- Distinguish certainty levels: "this IS a bug" vs "this COULD be a bug if X".
-- Don't invent problems to look thorough. If the code is solid, say so.
-- Focus on substance over style. Don't flag formatting unless it causes real confusion.
-- Respect existing project conventions (check CLAUDE.md). Don't flag patterns the project explicitly endorses.
-- When in doubt about severity, round up.
-- For large crates (>50 files), prioritize: core logic > public API > internal utilities > tests > examples.
-- Use the Task tool to parallelize file reading across modules when the crate is large.
-- Do NOT fix anything. This is a read-only audit. Report findings for the user to action.

.claude/commands/review-pr.md

@@ -1,170 +0,0 @@
----
-description: Paranoid architect review of a PR — fetches diff, reads changed files, deep review across 6 lenses, posts findings as GitHub comments
-disable-model-invocation: true
-allowed-tools: Bash(gh pr view:*), Bash(gh pr diff:*), Bash(gh pr comment:*), Bash(gh api:*), Bash(gh repo view:*), Bash(git diff:*), Bash(git log:*), Read, Grep, Glob
-argument-hint: "<pr-number or github-pr-url>"
----
-
-# Paranoid Architect Code Review
-
-You are reviewing this PR as a paranoid architect. Your job is to find every bug, vulnerability, race condition, edge case, and undocumented assumption before it ships. Assume adversarial users, concurrent access, and Murphy's law.
-
-## Step 1: Resolve the PR
-
-Parse `$ARGUMENTS` to extract the PR number:
-- If it's a URL like `https://github.com/owner/repo/pull/123`, extract `123`.
-- If it's a bare number, use it directly.
-- If empty, stop and ask the user for a PR number.
-
-Fetch PR metadata (including head commit SHA for posting line comments later):
-
-```
-gh pr view {number} --json title,body,baseRefName,headRefName,headRefOid,files,additions,deletions
-```
-
-Save the `headRefOid` value, you'll need it as `commit_id` in Step 6.
-
-## Step 2: Load the full diff
-
-```
-gh pr diff {number}
-```
-
-Also get the list of changed files:
-
-```
-gh pr diff {number} --name-only
-```
-
-## Step 3: Read every changed file in full
-
-For each changed file, read the ENTIRE current file (not just the diff hunks). You need surrounding context to catch:
-- Callers of modified functions that now behave differently
-- Trait/interface contracts that the change may violate
-- Invariants established elsewhere that the diff breaks
-
-If the PR touches more than 20 files, still read all of them, but process in this priority order: service logic > routes/handlers > models/types > tests > docs. Batch reads in groups of ~20 if needed.
-
-## Step 4: Deep review
-
-Go through the changes with each of these lenses. For every finding, note the file, line range, severity, and a concrete description.
-
-### IronClaw-specific checks
-
-In addition to the general lenses below, check IronClaw conventions (see CLAUDE.md):
-- No `.unwrap()` or `.expect()` in production code (tests are fine)
-- Use `crate::` imports, not `super::`
-- Error types use `thiserror` in `error.rs`
-- If the change touches persistence, verify both database backends are updated (PostgreSQL in `postgres.rs` AND libSQL in `libsql_backend.rs`)
-- New tools must implement the `Tool` trait correctly and be registered in `registry.rs`
-- External tool output must pass through the safety layer
-
-### 4a. Correctness and bugs
-
-- Off-by-one errors, wrong comparison operators, inverted conditions
-- Unreachable code, dead branches, impossible match arms
-- Type confusion (mixing up IDs, using wrong enum variant)
-- Incorrect error propagation (swallowed errors, wrong error type/status code)
-- Broken invariants (e.g. uniqueness assumptions violated, ordering assumptions wrong)
-- Concurrency issues (TOCTOU, missing locks, race conditions between check and use)
-
-### 4b. Edge cases and failure handling
-
-- What happens with empty input, None/null, zero-length collections?
-- What happens when external services fail (DB down, HTTP timeout, malformed response)?
-- What happens at integer boundaries (overflow, underflow, i64::MAX)?
-- What happens with malformed or adversarial input (invalid UTF-8, huge payloads, deeply nested JSON)?
-- Are all error paths tested? Does every `?` propagation make sense?
-- Are partial failures handled (e.g. wrote to DB but failed to emit event)?
-
-### 4c. Security (assume a malicious actor)
-
-- **Authentication/Authorization bypass**: Can an unauthenticated user reach this? Can workspace A's user access workspace B's data? Are there IDOR vulnerabilities?
-- **Injection**: SQL injection via string interpolation? Command injection? Log injection? Header injection?
-- **Data leakage**: Are secrets, PII, or conversation content logged? Returned in error messages? Exposed in API responses?
-- **Resource exhaustion / DoS**: Can an attacker send unbounded input? Trigger expensive operations without rate limits? Cause OOM via large allocations?
-- **Financial abuse**: Can tokens/credits be consumed without being tracked? Can usage limits be bypassed?
-- **Replay / race conditions**: Can the same request be replayed for double-spend? Can concurrent requests bypass limits?
-- **Cryptographic issues**: Timing attacks on comparisons? Weak randomness? Missing HMAC verification?
-
-### 4d. Test coverage
-
-- Is every new public function/method tested?
-- Are error paths tested (not just happy paths)?
-- Are edge cases covered (empty input, boundary values, concurrent access)?
-- Do existing tests still make sense with the new changes, or do they assert stale behavior?
-- Are there integration/e2e tests for the full flow?
-- If a test is missing, describe exactly what test should be written.
-
-### 4e. Documentation and assumptions
-
-- Are new assumptions documented in comments? (e.g. "this field is always non-empty because X")
-- Are non-obvious algorithms or business rules explained?
-- Are API contracts (request/response shapes, error codes, status codes) documented?
-- Are there TODO/FIXME/HACK comments that should be tracked as issues?
-
-### 4f. Architectural concerns
-
-- Does this change follow existing patterns in the codebase, or does it introduce a new one without justification?
-- Are there unnecessary abstractions or premature generalizations?
-- Is there duplicated logic that should be extracted?
-- Are dependencies between modules clean, or does this create circular/tight coupling?
-- Will this change make future work harder?
-
-## Step 5: Present findings
-
-Summarize findings to the user as a table:
-
-| # | Severity | Category | File:Line | Finding | Suggested Fix |
-|---|----------|----------|-----------|---------|---------------|
-
-Severity levels:
-- **Critical**: Security vulnerability, data loss, or financial exploit
-- **High**: Bug that will cause incorrect behavior in production
-- **Medium**: Robustness issue, missing validation, or incomplete error handling
-- **Low**: Style, naming, documentation, or minor improvement
-- **Nit**: Optional suggestion, take-it-or-leave-it
-
-Ask the user which findings to post as PR comments. Default: all Critical, High, and Medium.
-
-## Step 6: Post comments on GitHub
-
-Resolve the repo owner and name if not already known:
-
-```
-gh repo view --json owner,name --jq '"\(.owner.login)/\(.name)"'
-```
-
-For each approved finding, post a review comment on the PR at the specific file and line. Use the `headRefOid` from Step 1 as the `commit_id`:
-
-```
-gh api repos/{owner}/{repo}/pulls/{number}/comments \
-  -f body="..." \
-  -f path="..." \
-  -f commit_id="{headRefOid}" \
-  -F line=... \
-  -f side="RIGHT"
-```
-
-For findings that span multiple locations or are architectural, post as a regular PR comment:
-
-```
-gh pr comment {number} --body "..."
-```
-
-Format each comment clearly:
-- Severity tag (e.g. `**High Severity**`)
-- One-line summary
-- Detailed explanation of the issue
-- Concrete suggestion for the fix (with code if possible)
-
-## Rules
-
-- Read every changed file in full before writing a single finding. Context matters.
-- Never post a comment about code you haven't actually read. Verify line numbers against the actual file.
-- Be specific. "This might have issues" is useless. "Line 42 returns 404 but should return 400 because X" is useful.
-- Distinguish between "this IS a bug" and "this COULD be a bug if X". Be honest about certainty.
-- Don't nitpick formatting or style unless it causes actual confusion. Focus on substance.
-- If the code is good and you find nothing, say so. Don't invent problems to look thorough.
-- Respect the project's CLAUDE.md privacy rules: never include customer data, secrets, or PII in comments.
-- When in doubt about severity, round up. It's cheaper to dismiss a false alarm than to miss a real bug.

.github/workflows/release.yml

@@ -39,6 +39,7 @@ permissions:
 # If there's a prerelease-style suffix to the version, then the release(s)
 # will be marked as a prerelease.
 on:
+  pull_request:
   push:
     tags:
       - '**[0-9]+.[0-9]+.[0-9]+*'

.gitignore

@@ -1,15 +1,6 @@
 
 .env
 .env.local
-.env.*
-!.env.example
-
-# Claude Code worktrees
-.claude/worktrees/
-
-# Sidecar tool data
-.sidecar/
-.todos/
 
 target/
 

CHANGELOG.md

@@ -7,60 +7,6 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## [Unreleased]
 
-## [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
-
-- move per-invocation approval check into Tool trait ([#119](https://github.com/nearai/ironclaw/pull/119))
-- add polished boot screen on CLI startup ([#118](https://github.com/nearai/ironclaw/pull/118))
-- Add lifecycle hooks system with 6 interception points ([#18](https://github.com/nearai/ironclaw/pull/18))
-
-### Other
-
-- remove accidentally committed .sidecar and .todos directories ([#123](https://github.com/nearai/ironclaw/pull/123))
-
-## [0.3.0](https://github.com/nearai/ironclaw/compare/v0.2.0...v0.3.0) - 2026-02-17
-
-### Added
-
-- direct api key and cheap model ([#116](https://github.com/nearai/ironclaw/pull/116))
-
-## [0.2.0](https://github.com/nearai/ironclaw/compare/v0.1.3...v0.2.0) - 2026-02-16
-
-### Added
-
-- mark Ollama + OpenAI-compatible as implemented ([#102](https://github.com/nearai/ironclaw/pull/102))
-- multi-provider inference + libSQL onboarding selection ([#92](https://github.com/nearai/ironclaw/pull/92))
-- add multi-provider LLM failover with retry backoff ([#28](https://github.com/nearai/ironclaw/pull/28))
-- add libSQL/Turso embedded database backend ([#47](https://github.com/nearai/ironclaw/pull/47))
-- Move debug log truncation from agent loop to REPL channel ([#65](https://github.com/nearai/ironclaw/pull/65))
-
-### Fixed
-
-- shell destructive-command check bypassed by Value::Object arguments ([#72](https://github.com/nearai/ironclaw/pull/72))
-- propagate real tool_call_id instead of hardcoded placeholder ([#73](https://github.com/nearai/ironclaw/pull/73))
-- Fix wasm tool schemas and runtime ([#42](https://github.com/nearai/ironclaw/pull/42))
-- flatten tool messages for NEAR AI cloud-api compatibility ([#41](https://github.com/nearai/ironclaw/pull/41))
-- security hardening across all layers ([#35](https://github.com/nearai/ironclaw/pull/35))
-
-### Other
-
-- Explicitly enable cargo-dist caching for binary artifacts building
-- Skip building binary artifacts on every PR
-- add module specification rules to CLAUDE.md
-- add setup/onboarding specification (src/setup/README.md)
-- deduplicate tool code and remove dead stubs ([#98](https://github.com/nearai/ironclaw/pull/98))
-- Reformat architecture diagram in README ([#64](https://github.com/nearai/ironclaw/pull/64))
-- Add review discipline guidelines to CLAUDE.md ([#68](https://github.com/nearai/ironclaw/pull/68))
-- 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

@@ -198,9 +198,8 @@ When designing new features or systems, always prefer generic/extensible archite
 
 ### Error Handling
 - Use `thiserror` for error types in `error.rs`
-- Never use `.unwrap()` or `.expect()` in production code (tests are fine)
+- Never use `.unwrap()` in production code (tests are fine)
 - Map errors with context: `.map_err(|e| SomeError::Variant { reason: e.to_string() })?`
-- Before committing, grep for `.unwrap()` and `.expect(` in changed files to catch violations mechanically
 
 ### Async
 - All I/O is async with tokio
@@ -630,22 +629,6 @@ RUST_LOG=ironclaw::agent=debug cargo run
 RUST_LOG=ironclaw=debug,tower_http=debug cargo run
 ```
 
-## Module Specifications
-
-Some modules have a `README.md` that serves as the authoritative specification
-for that module's behavior. When modifying code in a module that has a spec:
-
-1. **Read the spec first** before making changes
-2. **Code follows spec**: if the spec says X, the code must do X
-3. **Update both sides**: if you change behavior, update the spec to match;
-   if you're implementing a spec change, update the code to match
-4. **Spec is the tiebreaker**: when code and spec disagree, the spec is correct
-   (unless the spec is clearly outdated, in which case fix the spec first)
-
-| Module | Spec File |
-|--------|-----------|
-| `src/setup/` | `src/setup/README.md` |
-
 ## Code Style
 
 - Use `crate::` imports, not `super::`
@@ -654,37 +637,6 @@ for that module's behavior. When modifying code in a module that has a spec:
 - 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/`
-
 ## Workspace & Memory System
 
 Inspired by [OpenClaw](https://github.com/openclaw/openclaw), the workspace provides persistent memory for agents with a flexible filesystem-like structure.

Cargo.lock

@@ -2210,11 +2210,11 @@ dependencies = [
  "hyper 1.8.1",
  "hyper-util",
  "rustls",
- "rustls-native-certs",
  "rustls-pki-types",
  "tokio",
  "tokio-rustls",
  "tower-service",
+ "webpki-roots",
 ]
 
 [[package]]
@@ -2490,7 +2490,7 @@ dependencies = [
 
 [[package]]
 name = "ironclaw"
-version = "0.5.0"
+version = "0.1.3"
 dependencies = [
  "aes-gcm",
  "aho-corasick",
@@ -2548,7 +2548,6 @@ dependencies = [
  "tower-http 0.6.8",
  "tracing",
  "tracing-subscriber",
- "url",
  "urlencoding",
  "uuid",
  "wasmparser 0.220.1",
@@ -4034,7 +4033,6 @@ dependencies = [
  "pin-project-lite",
  "quinn",
  "rustls",
- "rustls-native-certs",
  "rustls-pki-types",
  "serde",
  "serde_json",
@@ -4052,6 +4050,7 @@ dependencies = [
  "wasm-bindgen-futures",
  "wasm-streams",
  "web-sys",
+ "webpki-roots",
 ]
 
 [[package]]
@@ -6238,6 +6237,15 @@ dependencies = [
  "wasm-bindgen",
 ]
 
+[[package]]
+name = "webpki-roots"
+version = "1.0.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "12bed680863276c63889429bfd6cab3b99943659923822de1c8a39c49e4d722c"
+dependencies = [
+ "rustls-pki-types",
+]
+
 [[package]]
 name = "which"
 version = "4.4.2"

Cargo.toml

@@ -1,16 +1,8 @@
-[workspace]
-exclude = [
-    "channels-src/telegram",
-    "channels-src/slack",
-    "channels-src/whatsapp",
-    "tools-src/gmail",
-]
-
 [package]
 name = "ironclaw"
-version = "0.5.0"
+version = "0.1.3"
 edition = "2024"
-rust-version = "1.92"
+rust-version = "1.85"
 description = "Secure personal AI assistant that protects your data and expands its capabilities on the fly"
 authors = ["NEAR AI <[email protected]>"]
 license = "MIT OR Apache-2.0"
@@ -30,7 +22,7 @@ tokio-stream = { version = "0.1", features = ["sync"] }
 futures = "0.3"
 
 # HTTP client
-reqwest = { version = "0.12", default-features = false, features = ["json", "rustls-tls-native-roots", "stream"] }
+reqwest = { version = "0.12", default-features = false, features = ["json", "rustls-tls", "stream"] }
 
 # Serialization
 serde = { version = "1", features = ["derive"] }
@@ -92,8 +84,7 @@ fs4 = "0.6"
 # Secrecy for sensitive values
 secrecy = { version = "0.10", features = ["serde"] }
 
-# URL parsing and encoding
-url = "2"
+# URL encoding for OAuth flow
 urlencoding = "2"
 
 # Open URLs in browser
@@ -147,7 +138,7 @@ pretty_assertions = "1"
 tempfile = "3"
 
 [features]
-default = ["postgres", "libsql"]
+default = ["postgres"]
 postgres = [
     "dep:deadpool-postgres",
     "dep:tokio-postgres",
@@ -191,13 +182,11 @@ windows-archive = ".tar.gz"
 # The archive format to use for non-windows builds (defaults .tar.xz)
 unix-archive = ".tar.gz"
 # Which actions to run on pull requests
-pr-run-mode = "skip"
+pr-run-mode = "upload"
 # Path that installers should place binaries in
 install-path = "CARGO_HOME"
 # Whether to install an updater program
 install-updater = true
-# Cache intermediate build artifacts to speed up the release pipelines
-cache-builds = true
 
 [workspace.metadata.dist.github-custom-runners]
 aarch64-unknown-linux-gnu = "ubuntu-24.04-arm"

Dockerfile

@@ -1,46 +0,0 @@
-# Multi-stage Dockerfile for the IronClaw agent (cloud deployment).
-#
-# Build:
-#   docker build --platform linux/amd64 -t ironclaw:latest .
-#
-# Run:
-#   docker run --env-file .env -p 3000:3000 ironclaw:latest
-
-# Stage 1: Build
-FROM rust:1.92-slim-bookworm AS builder
-
-RUN apt-get update && apt-get install -y --no-install-recommends \
-    pkg-config libssl-dev cmake gcc g++ \
-    && rm -rf /var/lib/apt/lists/*
-
-WORKDIR /app
-
-# Copy manifests first for layer caching
-COPY Cargo.toml Cargo.lock ./
-
-# Copy source and build artifacts
-COPY src/ src/
-COPY migrations/ migrations/
-COPY wit/ wit/
-
-RUN cargo build --release --bin ironclaw
-
-# Stage 2: Runtime
-FROM debian:bookworm-slim
-
-RUN apt-get update && apt-get install -y --no-install-recommends \
-    ca-certificates libssl3 \
-    && rm -rf /var/lib/apt/lists/*
-
-COPY --from=builder /app/target/release/ironclaw /usr/local/bin/ironclaw
-COPY --from=builder /app/migrations /app/migrations
-
-# Non-root user
-RUN useradd -m -u 1000 -s /bin/bash ironclaw
-USER ironclaw
-
-EXPOSE 3000
-
-ENV RUST_LOG=ironclaw=info
-
-ENTRYPOINT ["ironclaw"]

Dockerfile.worker

@@ -9,7 +9,7 @@
 # The image includes common development tools so workers can build software,
 # run tests, and execute shell commands.
 
-FROM rust:1.92-bookworm AS builder
+FROM rust:1.85-bookworm AS builder
 
 WORKDIR /build
 COPY . .
@@ -40,7 +40,7 @@ RUN apt-get update && apt-get install -y --no-install-recommends \
 ENV RUSTUP_HOME=/usr/local/rustup \
     CARGO_HOME=/usr/local/cargo \
     PATH=/usr/local/cargo/bin:$PATH
-RUN curl --proto '=https' --tlsv1.2 -sSf https://sh.rustup.rs | sh -s -- -y --default-toolchain 1.92.0 \
+RUN curl --proto '=https' --tlsv1.2 -sSf https://sh.rustup.rs | sh -s -- -y --default-toolchain 1.85.0 \
     && chmod -R a+r /usr/local/rustup /usr/local/cargo
 
 # Install Claude Code CLI (for claude-bridge mode)

FEATURE_PARITY.md

@@ -112,7 +112,7 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | `pairing` | ✅ | ✅ | - | list/approve for channel DM pairing |
 | `nodes` | ✅ | ❌ | P3 | Device management |
 | `plugins` | ✅ | ❌ | P3 | Plugin management |
-| `hooks` | ✅ | ✅ | P2 | Lifecycle hooks |
+| `hooks` | ✅ | ❌ | P2 | Lifecycle hooks |
 | `cron` | ✅ | ❌ | P2 | Scheduled jobs |
 | `webhooks` | ✅ | ❌ | P3 | Webhook config |
 | `message send` | ✅ | ❌ | P2 | Send to channels |
@@ -133,7 +133,7 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 |---------|----------|----------|-------|
 | Pi agent runtime | ✅ | ➖ | IronClaw uses custom runtime |
 | RPC-based execution | ✅ | ✅ | Orchestrator/worker pattern |
-| Multi-provider failover | ✅ | ✅ | `FailoverProvider` tries providers sequentially on retryable errors |
+| Multi-provider failover | ✅ | ❌ | Provider fallback chains |
 | Per-sender sessions | ✅ | ✅ | |
 | Global sessions | ✅ | ❌ | Optional shared context |
 | Session pruning | ✅ | ❌ | Auto cleanup old sessions |
@@ -164,7 +164,7 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | AWS Bedrock | ✅ | ❌ | P3 | |
 | Google Gemini | ✅ | ❌ | P3 | |
 | OpenRouter | ✅ | ❌ | P3 | |
-| Ollama (local) | ✅ | ✅ | - | via `rig::providers::ollama` (full support) |
+| Ollama (local) | ✅ | ❌ | P2 | Local models |
 | node-llama-cpp | ✅ | ➖ | - | N/A for Rust |
 | llama.cpp (native) | ❌ | 🔮 | P3 | Rust bindings |
 
@@ -173,8 +173,8 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Feature | OpenClaw | IronClaw | Notes |
 |---------|----------|----------|-------|
 | Auto-discovery | ✅ | ❌ | |
-| Failover chains | ✅ | ✅ | `FailoverProvider` with configurable `fallback_model` |
-| Cooldown management | ✅ | ✅ | Lock-free per-provider cooldown in `FailoverProvider` |
+| Failover chains | ✅ | ❌ | Provider fallback |
+| Cooldown management | ✅ | ❌ | Skip failed providers |
 | Per-session model override | ✅ | ✅ | Model selector in TUI |
 | Model selection UI | ✅ | ✅ | TUI keyboard shortcut |
 
@@ -323,14 +323,14 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Cron jobs | ✅ | ✅ | - | Routines with cron trigger |
 | Timezone support | ✅ | ✅ | - | Via cron expressions |
 | One-shot/recurring jobs | ✅ | ✅ | - | Manual + cron triggers |
-| `beforeInbound` hook | ✅ | ✅ | P2 | |
-| `beforeOutbound` hook | ✅ | ✅ | P2 | |
-| `beforeToolCall` hook | ✅ | ✅ | P2 | |
+| `beforeInbound` hook | ✅ | ❌ | P2 | |
+| `beforeOutbound` hook | ✅ | ❌ | P2 | |
+| `beforeToolCall` hook | ✅ | ❌ | P2 | |
 | `onMessage` hook | ✅ | ✅ | - | Routines with event trigger |
-| `onSessionStart` hook | ✅ | ✅ | P2 | |
-| `onSessionEnd` hook | ✅ | ✅ | P2 | |
+| `onSessionStart` hook | ✅ | ❌ | P2 | |
+| `onSessionEnd` hook | ✅ | ❌ | P2 | |
 | `transcribeAudio` hook | ✅ | ❌ | P3 | |
-| `transformResponse` hook | ✅ | ✅ | P2 | |
+| `transformResponse` hook | ✅ | ❌ | P2 | |
 | Bundled hooks | ✅ | ❌ | P2 | |
 | Plugin hooks | ✅ | ❌ | P3 | |
 | Workspace hooks | ✅ | ❌ | P2 | Inline code |
@@ -419,11 +419,15 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 - ❌ 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)
+- ❌ Multi-provider failover
+- ❌ Hooks system (beforeInbound, beforeToolCall, etc.)
 
 ### P2 - Medium Priority
-- ❌ Media handling (images, PDFs)
+- ❌ Cron job scheduling
+- ❌ Web Control UI
+- ❌ WebChat channel
+- 🚧 Media handling (caption support; no image/PDF processing)
+- ❌ CLI subcommands (config, status, memory, doctor)
 - ❌ Ollama/local model support
 - ❌ Configuration hot-reload
 - ❌ Webhook trigger endpoint in web gateway

README.md

@@ -181,42 +181,42 @@ External content passes through multiple security layers:
 ## Architecture
 
 ```
-┌────────────────────────────────────────────────────────────────┐
-│                          Channels                              │
-│  ┌──────┐  ┌──────┐   ┌─────────────┐  ┌─────────────┐         │
-│  │ REPL │  │ HTTP │   │WASM Channels│  │ Web Gateway │         │
-│  └──┬───┘  └──┬───┘   └──────┬──────┘  │ (SSE + WS)  │         │
-│     │         │              │         └──────┬──────┘         │
-│     └─────────┴──────────────┴────────────────┘                │
-│                              │                                 │
-│                    ┌─────────▼─────────┐                       │
-│                    │    Agent Loop     │  Intent routing       │
-│                    └────┬──────────┬───┘                       │
-│                         │          │                           │
-│              ┌──────────▼────┐  ┌──▼───────────────┐           │
-│              │  Scheduler    │  │ Routines Engine  │           │
-│              │(parallel jobs)│  │(cron, event, wh) │           │
-│              └──────┬────────┘  └────────┬─────────┘           │
-│                     │                    │                     │
-│       ┌─────────────┼────────────────────┘                     │
-│       │             │                                          │
-│   ┌───▼─────┐  ┌────▼────────────────┐                         │
-│   │ Local   │  │    Orchestrator     │                         │
-│   │Workers  │  │  ┌───────────────┐  │                         │
-│   │(in-proc)│  │  │ Docker Sandbox│  │                         │
-│   └───┬─────┘  │  │   Containers  │  │                         │
-│       │        │  │ ┌───────────┐ │  │                         │
-│       │        │  │ │Worker / CC│ │  │                         │
-│       │        │  │ └───────────┘ │  │                         │
-│       │        │  └───────────────┘  │                         │
-│       │        └─────────┬───────────┘                         │
-│       └──────────────────┤                                     │
-│                          │                                     │
-│              ┌───────────▼──────────┐                          │
-│              │    Tool Registry     │                          │
-│              │  Built-in, MCP, WASM │                          │
-│              └──────────────────────┘                          │
-└────────────────────────────────────────────────────────────────┘
+┌────────────────────────────────────────────────────────────────────┐
+│                          Channels                                  │
+│  ┌──────┐  ┌──────┐  ┌─────────────┐  ┌─────────────┐            │
+│  │ REPL │  │ HTTP │  │WASM Channels│  │ Web Gateway │            │
+│  └──┬───┘  └──┬───┘  └──────┬──────┘  │ (SSE + WS) │            │
+│     │         │              │         └──────┬──────┘            │
+│     └─────────┴──────────────┴────────────────┘                   │
+│                              │                                     │
+│                    ┌─────────▼─────────┐                          │
+│                    │    Agent Loop     │  Intent routing           │
+│                    └────┬─────────┬────┘                          │
+│                         │         │                                │
+│              ┌──────────▼───┐  ┌──▼──────────────┐               │
+│              │  Scheduler   │  │ Routines Engine  │               │
+│              │(parallel jobs)│  │(cron, event, wh) │               │
+│              └──────┬───────┘  └────────┬─────────┘               │
+│                     │                   │                          │
+│       ┌─────────────┼───────────────────┘                         │
+│       │             │                                              │
+│   ┌───▼────┐   ┌────▼────────────────┐                           │
+│   │ Local  │   │    Orchestrator     │                           │
+│   │Workers │   │  ┌───────────────┐  │                           │
+│   │(in-proc)│   │  │ Docker Sandbox│  │                           │
+│   └───┬────┘   │  │   Containers  │  │                           │
+│       │        │  │ ┌───────────┐ │  │                           │
+│       │        │  │ │Worker / CC│ │  │                           │
+│       │        │  │ └───────────┘ │  │                           │
+│       │        │  └───────────────┘  │                           │
+│       │        └─────────┬───────────┘                           │
+│       └──────────────────┤                                        │
+│                          │                                        │
+│              ┌───────────▼──────────┐                             │
+│              │    Tool Registry     │                             │
+│              │  Built-in, MCP, WASM │                             │
+│              └──────────────────────┘                             │
+└────────────────────────────────────────────────────────────────────┘
 ```
 
 ### Core Components

channels-src/discord/Cargo.toml

@@ -1,23 +0,0 @@
-[package]
-name = "discord-channel"
-version = "0.1.0"
-edition = "2021"
-description = "Discord channel for IronClaw"
-license = "MIT OR Apache-2.0"
-publish = false
-
-[dependencies]
-serde = { version = "1.0", features = ["derive"] }
-serde_json = "1.0"
-wit-bindgen = "0.41.0"
-
-[lib]
-crate-type = ["cdylib"]
-
-[profile.release]
-strip = true
-opt-level = "s"
-lto = true
-codegen-units = 1
-
-

channels-src/discord/README.md

@@ -1,121 +0,0 @@
-# Discord Channel for IronClaw
-
-WASM channel for Discord integration - handle slash commands and button interactions via webhooks.
-
-## Features
-
-- **Slash Commands** - Process Discord slash commands
-- **Button Interactions** - Handle button clicks
-- **Thread Support** - Respond in threads
-- **DM Support** - Handle direct messages
-
-## Setup
-
-1. Create a Discord Application at <https://discord.com/developers/applications>
-2. Create a Bot and get the token
-3. Set up Interactions URL to point to your IronClaw instance
-4. Copy the Application ID and Public Key
-5. Store in IronClaw secrets:
-
-   ```bash
-   ironclaw secret set discord_bot_token YOUR_BOT_TOKEN
-   ```
-
-   **Note:** The `discord_bot_token` secret is the only value read directly by this
-   Discord channel WASM component. The `discord_app_id` and `discord_public_key`
-   secrets are used by the IronClaw host (for example, to verify Discord
-   interaction signatures and manage slash command registration) and are not
-   accessed from the WASM module itself.
-
-## Discord Configuration
-
-### Register Slash Commands
-
-```bash
-curl -X POST \
-  -H "Authorization: Bot YOUR_BOT_TOKEN" \
-  -H "Content-Type: application/json" \
-  https://discord.com/api/v10/applications/YOUR_APP_ID/commands \
-  -d '{
-    "name": "ask",
-    "description": "Ask the AI agent",
-    "options": [{
-      "name": "question",
-      "description": "Your question",
-      "type": 3,
-      "required": true
-    }]
-  }'
-```
-
-### Set Interactions Endpoint
-
-In your Discord app settings, set:
-
-- Interactions Endpoint URL: `https://your-ironclaw.com/webhook/discord`
-
-## Usage Examples
-
-### Slash Command
-
-User types: `/ask question: What is the weather?`
-
-The agent receives:
-
-```text
-User: @username
-Content: /ask question: What is the weather?
-```
-
-### Button Click
-
-When a user clicks a button in a message, the agent receives:
-
-```text
-User: @username
-Content: [Button clicked] Original message content
-```
-
-## Error Handling
-
-If an internal error occurs (e.g., metadata serialization failure), the tool attempts to send an ephemeral message to the user:
-
-```text
-❌ Internal Error: Failed to process command metadata.
-```
-
-Check the host logs for detailed error information.
-
-## Advanced Usage
-
-### Embeds
-
-To send embeds, include an `embeds` array in the `metadata_json` field of the agent's response. The structure should match the Discord API `embed` object.
-
-## Troubleshooting
-
-### "Invalid Signature"
-
-- Check that `discord_public_key` is set correctly in IronClaw secrets.
-- This validation happens on the host before reaching the WASM.
-
-### "401 Unauthorized"
-
-- Check that `discord_bot_token` is set correctly in IronClaw secrets.
-- Ensure the bot is added to the server.
-
-### "Interaction Failed"
-
-- The interaction might have timed out (Discord requires a response within 3 seconds).
-- The `interactions_endpoint_url` might be unreachable.
-
-## Building
-
-```bash
-cd channels-src/discord
-cargo build --target wasm32-wasi --release
-```
-
-## License
-
-MIT/Apache-2.0

channels-src/discord/discord.capabilities.json

@@ -1,39 +0,0 @@
-{
-  "type": "channel",
-  "name": "discord",
-  "description": "Discord Gateway/Webhook channel for handling slash commands, buttons, and messages",
-  "capabilities": {
-    "http": {
-      "allowlist": [
-        { "host": "discord.com", "path_prefix": "/api/v10" }
-      ],
-      "credentials": {
-        "discord_bot_token": {
-          "secret_name": "discord_bot_token",
-          "location": { "type": "header", "header_name": "Authorization", "prefix": "Bot " },
-          "host_patterns": ["discord.com"]
-        }
-      },
-      "rate_limit": {
-        "requests_per_minute": 60,
-        "requests_per_hour": 3600
-      }
-    },
-    "secrets": {
-      "allowed_names": ["discord_bot_token", "discord_*"]
-    },
-    "channel": {
-      "allowed_paths": ["/webhook/discord"],
-      "allow_polling": false,
-      "callback_timeout_secs": 45,
-      "workspace_prefix": "channels/discord/",
-      "emit_rate_limit": {
-        "messages_per_minute": 100,
-        "messages_per_hour": 5000
-      }
-    }
-  },
-  "config": {
-    "require_signature_verification": true
-  }
-}

channels-src/discord/src/lib.rs

@@ -1,476 +0,0 @@
-//! Discord Gateway/Webhook channel for IronClaw.
-//!
-//! This WASM component implements the channel interface for handling Discord
-//! interactions via webhooks and sending messages back to Discord.
-//!
-//! # Features
-//!
-//! - URL verification for Discord interactions
-//! - Slash command handling
-//! - Message event parsing (@mentions, DMs)
-//! - Thread support for conversations
-//! - Response posting via Discord Web API
-//! - Automatic message truncation (> 2000 chars)
-//!
-//! # Security
-//!
-//! - Signature validation is handled by the host (webhook secrets)
-//! - Bot token is injected by host during HTTP requests
-//! - WASM never sees raw credentials
-
-wit_bindgen::generate!({
-    world: "sandboxed-channel",
-    path: "../../wit/channel.wit",
-});
-
-use serde::{Deserialize, Serialize};
-
-use exports::near::agent::channel::{
-    AgentResponse, ChannelConfig, Guest, HttpEndpointConfig, IncomingHttpRequest,
-    OutgoingHttpResponse, StatusUpdate,
-};
-use near::agent::channel_host::{self, EmittedMessage};
-
-/// Discord interaction wrapper.
-#[derive(Debug, Deserialize)]
-struct DiscordInteraction {
-    /// Interaction type (1=Ping, 2=ApplicationCommand, 3=MessageComponent)
-    #[serde(rename = "type")]
-    interaction_type: u8,
-
-    /// Interaction ID
-    id: String,
-
-    /// Application ID
-    application_id: String,
-
-    /// Guild ID (if in server)
-    #[allow(dead_code)] // Part of API payload, currently unused
-    guild_id: Option<String>,
-
-    /// Channel ID
-    channel_id: Option<String>,
-
-    /// Member info (if in server)
-    member: Option<DiscordMember>,
-
-    /// User info (if DM)
-    user: Option<DiscordUser>,
-
-    /// Command data (for slash commands)
-    data: Option<DiscordCommandData>,
-
-    /// Message (for component interactions)
-    message: Option<DiscordMessage>,
-
-    /// Token for responding
-    token: String,
-}
-
-#[derive(Debug, Deserialize, Clone)]
-struct DiscordMember {
-    user: DiscordUser,
-    #[allow(dead_code)] // Part of API payload, currently unused
-    nick: Option<String>,
-}
-
-#[derive(Debug, Deserialize, Clone)]
-struct DiscordUser {
-    id: String,
-    username: String,
-    global_name: Option<String>,
-}
-
-#[derive(Debug, Deserialize, Clone)]
-struct DiscordCommandData {
-    #[allow(dead_code)] // Part of API payload, currently unused
-    id: String,
-    name: String,
-    options: Option<Vec<DiscordCommandOption>>,
-}
-
-#[derive(Debug, Deserialize, Clone)]
-struct DiscordCommandOption {
-    name: String,
-    value: serde_json::Value,
-}
-
-#[derive(Debug, Deserialize, Clone)]
-struct DiscordMessage {
-    #[allow(dead_code)] // Part of API payload, currently unused
-    id: String,
-    content: String,
-    channel_id: String,
-    #[allow(dead_code)] // Part of API payload, currently unused
-    author: DiscordUser,
-}
-
-/// Metadata stored with emitted messages for response routing.
-#[derive(Debug, Serialize, Deserialize)]
-struct DiscordMessageMetadata {
-    /// Discord channel ID
-    channel_id: String,
-
-    /// Interaction ID for followups
-    interaction_id: String,
-
-    /// Interaction token for responding
-    token: String,
-
-    /// Application ID
-    application_id: String,
-
-    /// Thread ID (for forum threads)
-    thread_id: Option<String>,
-}
-
-struct DiscordChannel;
-
-impl Guest for DiscordChannel {
-    fn on_start(_config_json: String) -> Result<ChannelConfig, String> {
-        channel_host::log(channel_host::LogLevel::Info, "Discord channel starting");
-
-        Ok(ChannelConfig {
-            display_name: "Discord".to_string(),
-            http_endpoints: vec![HttpEndpointConfig {
-                path: "/webhook/discord".to_string(),
-                methods: vec!["POST".to_string()],
-                require_secret: true,
-            }],
-            poll: None,
-        })
-    }
-
-    fn on_http_request(req: IncomingHttpRequest) -> OutgoingHttpResponse {
-        let body_str = match std::str::from_utf8(&req.body) {
-            Ok(s) => s,
-            Err(_) => {
-                return json_response(400, serde_json::json!({"error": "Invalid UTF-8 body"}));
-            }
-        };
-
-        let interaction: DiscordInteraction = match serde_json::from_str(body_str) {
-            Ok(i) => i,
-            Err(e) => {
-                channel_host::log(
-                    channel_host::LogLevel::Error,
-                    &format!("Failed to parse Discord interaction: {}", e),
-                );
-                return json_response(400, serde_json::json!({"error": "Invalid interaction"}));
-            }
-        };
-
-        match interaction.interaction_type {
-            // Ping - Discord verification
-            1 => {
-                channel_host::log(channel_host::LogLevel::Info, "Responding to Discord ping");
-                json_response(200, serde_json::json!({"type": 1}))
-            }
-
-            // Application Command (slash command)
-            2 => {
-                handle_slash_command(&interaction);
-                json_response(
-                    200,
-                    serde_json::json!({
-                        "type": 5,
-                        "data": {
-                            "content": "🤔 Thinking..."
-                        }
-                    }),
-                )
-            }
-
-            // Message Component (buttons, selects)
-            3 => {
-                if let Some(ref message) = interaction.message {
-                    handle_message_component(&interaction, message);
-                }
-                json_response(200, serde_json::json!({"type": 6}))
-            }
-
-            _ => {
-                channel_host::log(
-                    channel_host::LogLevel::Warn,
-                    &format!(
-                        "Unknown Discord interaction type: {}",
-                        interaction.interaction_type
-                    ),
-                );
-                json_response(200, serde_json::json!({"type": 6}))
-            }
-        }
-    }
-
-    fn on_poll() {}
-
-    fn on_respond(response: AgentResponse) -> Result<(), String> {
-        let metadata: DiscordMessageMetadata = serde_json::from_str(&response.metadata_json)
-            .map_err(|e| format!("Failed to parse metadata: {}", e))?;
-
-        // Use webhook endpoint for followup
-        let url = format!(
-            "https://discord.com/api/v10/webhooks/{}/{}",
-            metadata.application_id, metadata.token
-        );
-
-        // Truncate content to 2000 characters to comply with Discord limits
-        let content = truncate_message(&response.content);
-
-        let mut payload = serde_json::json!({
-            "content": content,
-        });
-
-        // Check for embeds in metadata
-        if let Ok(meta_json) = serde_json::from_str::<serde_json::Value>(&response.metadata_json) {
-            if let Some(embeds) = meta_json.get("embeds") {
-                payload["embeds"] = embeds.clone();
-            }
-        }
-
-        let payload_bytes =
-            serde_json::to_vec(&payload).map_err(|e| format!("Failed to serialize: {}", e))?;
-
-        let headers = serde_json::json!({
-            "Content-Type": "application/json"
-        });
-
-        let result = channel_host::http_request(
-            "POST",
-            &url,
-            &headers.to_string(),
-            Some(&payload_bytes),
-            None,
-        );
-
-        match result {
-            Ok(http_response) => {
-                if http_response.status >= 200 && http_response.status < 300 {
-                    channel_host::log(channel_host::LogLevel::Debug, "Posted followup to Discord");
-                    Ok(())
-                } else {
-                    let body_str = String::from_utf8_lossy(&http_response.body);
-                    Err(format!(
-                        "Discord API error: {} - {}",
-                        http_response.status, body_str
-                    ))
-                }
-            }
-            Err(e) => Err(format!("HTTP request failed: {}", e)),
-        }
-    }
-
-    fn on_status(_update: StatusUpdate) {}
-
-    fn on_shutdown() {
-        channel_host::log(
-            channel_host::LogLevel::Info,
-            "Discord channel shutting down",
-        );
-    }
-}
-
-fn handle_slash_command(interaction: &DiscordInteraction) {
-    let user = interaction
-        .member
-        .as_ref()
-        .map(|m| &m.user)
-        .or(interaction.user.as_ref());
-    let user_id = user.map(|u| u.id.clone()).unwrap_or_default();
-    let user_name = user
-        .map(|u| {
-            u.global_name
-                .as_ref()
-                .filter(|s| !s.is_empty())
-                .unwrap_or(&u.username)
-                .clone()
-        })
-        .unwrap_or_default();
-
-    let channel_id = interaction.channel_id.clone().unwrap_or_default();
-
-    let command_name = interaction
-        .data
-        .as_ref()
-        .map(|d| d.name.clone())
-        .unwrap_or_default();
-    let options = interaction.data.as_ref().and_then(|d| d.options.clone());
-
-    let content = if let Some(opts) = options {
-        let opt_str = opts
-            .iter()
-            .map(|o| format!("{}: {}", o.name, o.value))
-            .collect::<Vec<_>>()
-            .join(", ");
-        format!("/{} {}", command_name, opt_str)
-    } else {
-        format!("/{}", command_name)
-    };
-
-    let metadata = DiscordMessageMetadata {
-        channel_id: channel_id.clone(),
-        interaction_id: interaction.id.clone(),
-        token: interaction.token.clone(),
-        application_id: interaction.application_id.clone(),
-        thread_id: None,
-    };
-
-    let metadata_json = match serde_json::to_string(&metadata) {
-        Ok(json) => json,
-        Err(e) => {
-            channel_host::log(
-                channel_host::LogLevel::Error,
-                &format!("Failed to serialize metadata: {}", e),
-            );
-            // Attempt to notify user of internal error
-            let url = format!(
-                "https://discord.com/api/v10/webhooks/{}/{}",
-                interaction.application_id, interaction.token
-            );
-            let payload = serde_json::json!({
-                "content": "❌ Internal Error: Failed to process command metadata.",
-                "flags": 64 // Ephemeral
-            });
-            let _ = channel_host::http_request(
-                "POST",
-                &url,
-                &serde_json::json!({"Content-Type": "application/json"}).to_string(),
-                Some(&serde_json::to_vec(&payload).unwrap_or_default()),
-                None,
-            );
-            return;
-        }
-    };
-
-    channel_host::emit_message(&EmittedMessage {
-        user_id,
-        user_name: Some(user_name),
-        content,
-        thread_id: None,
-        metadata_json,
-    });
-}
-
-fn handle_message_component(interaction: &DiscordInteraction, message: &DiscordMessage) {
-    // Check member first (for server contexts), then user (for DMs)
-    let user = interaction
-        .member
-        .as_ref()
-        .map(|m| &m.user)
-        .or(interaction.user.as_ref());
-    let user_id = user.map(|u| u.id.clone()).unwrap_or_default();
-    let user_name = user
-        .map(|u| {
-            u.global_name
-                .as_ref()
-                .filter(|s| !s.is_empty())
-                .unwrap_or(&u.username)
-                .clone()
-        })
-        .unwrap_or_default();
-
-    let channel_id = message.channel_id.clone();
-
-    let metadata = DiscordMessageMetadata {
-        channel_id: channel_id.clone(),
-        interaction_id: interaction.id.clone(),
-        token: interaction.token.clone(),
-        application_id: interaction.application_id.clone(),
-        thread_id: None,
-    };
-
-    let metadata_json = match serde_json::to_string(&metadata) {
-        Ok(json) => json,
-        Err(e) => {
-            channel_host::log(
-                channel_host::LogLevel::Error,
-                &format!("Failed to serialize metadata: {}", e),
-            );
-            return; // Don't emit message if metadata can't be serialized
-        }
-    };
-
-    channel_host::emit_message(&EmittedMessage {
-        user_id,
-        user_name: Some(user_name),
-        content: format!("[Button clicked] {}", message.content),
-        thread_id: None,
-        metadata_json,
-    });
-}
-
-fn json_response(status: u16, value: serde_json::Value) -> OutgoingHttpResponse {
-    let body = serde_json::to_vec(&value).unwrap_or_default();
-    let headers = serde_json::json!({"Content-Type": "application/json"});
-
-    OutgoingHttpResponse {
-        status,
-        headers_json: headers.to_string(),
-        body,
-    }
-}
-
-export!(DiscordChannel);
-
-fn truncate_message(content: &str) -> String {
-    if content.len() <= 2000 {
-        content.to_string()
-    } else {
-        let max_bytes = 1990;
-        let cutoff = content
-            .char_indices()
-            .map(|(i, c)| i + c.len_utf8())
-            .take_while(|&end| end <= max_bytes)
-            .last()
-            .unwrap_or(0);
-        let mut truncated = content[..cutoff].to_string();
-        truncated.push_str("\n... (truncated)");
-        truncated
-    }
-}
-
-#[cfg(test)]
-mod tests {
-    use super::*;
-
-    #[test]
-    fn test_truncate_message() {
-        let short = "Hello world";
-        assert_eq!(truncate_message(short), short);
-
-        let long = "a".repeat(2005);
-        let truncated = truncate_message(&long);
-        assert_eq!(truncated.len(), 2006); // 1990 + 16 chars suffix
-        assert!(truncated.ends_with("\n... (truncated)"));
-
-        // Test with multibyte characters (Euro sign is 3 bytes)
-        // 1000 chars * 3 bytes = 3000 bytes
-        let multi = "€".repeat(1000);
-        let truncated_multi = truncate_message(&multi);
-
-        // 1990 bytes limit. 1990 / 3 = 663 with remainder 1.
-        // Should truncate at 663 chars (1989 bytes).
-        // Suffix is 16 bytes. Total: 1989 + 16 = 2005 bytes.
-        assert!(truncated_multi.len() <= 2006);
-        assert!(truncated_multi.len() >= 2006 - 4); // Allow for max utf8 char width variance
-        assert!(truncated_multi.ends_with("\n... (truncated)"));
-
-        let content_part = &truncated_multi[..truncated_multi.len() - 16];
-        assert!(content_part.chars().all(|c| c == '€'));
-    }
-
-    #[test]
-    fn test_metadata_serialization() {
-        let metadata = DiscordMessageMetadata {
-            channel_id: "123".into(),
-            interaction_id: "456".into(),
-            token: "abc".into(),
-            application_id: "789".into(),
-            thread_id: None,
-        };
-        let json = serde_json::to_string(&metadata).unwrap();
-        let parsed: DiscordMessageMetadata = serde_json::from_str(&json).unwrap();
-        assert_eq!(parsed.channel_id, "123");
-        assert_eq!(parsed.interaction_id, "456");
-    }
-}

channels-src/slack/src/lib.rs

@@ -338,13 +338,7 @@ fn emit_message(
         team_id,
     };
 
-    let metadata_json = serde_json::to_string(&metadata).unwrap_or_else(|e| {
-        channel_host::log(
-            channel_host::LogLevel::Error,
-            &format!("Failed to serialize Slack metadata: {}", e),
-        );
-        "{}".to_string()
-    });
+    let metadata_json = serde_json::to_string(&metadata).unwrap_or_else(|_| "{}".to_string());
 
     // Strip @ mentions of the bot from the text for cleaner messages
     let cleaned_text = strip_bot_mention(&text);
@@ -372,13 +366,7 @@ fn strip_bot_mention(text: &str) -> String {
 
 /// Create a JSON HTTP response.
 fn json_response(status: u16, value: serde_json::Value) -> OutgoingHttpResponse {
-    let body = serde_json::to_vec(&value).unwrap_or_else(|e| {
-        channel_host::log(
-            channel_host::LogLevel::Error,
-            &format!("Failed to serialize JSON response: {}", e),
-        );
-        Vec::new()
-    });
+    let body = serde_json::to_vec(&value).unwrap_or_default();
     let headers = serde_json::json!({"Content-Type": "application/json"});
 
     OutgoingHttpResponse {

channels-src/telegram/src/lib.rs

@@ -285,7 +285,11 @@ impl Guest for TelegramChannel {
         }
 
         // Persist dm_policy and allow_from for DM pairing in handle_message
-        let dm_policy = config.dm_policy.as_deref().unwrap_or("pairing").to_string();
+        let dm_policy = config
+            .dm_policy
+            .as_deref()
+            .unwrap_or("pairing")
+            .to_string();
         let _ = channel_host::workspace_write(DM_POLICY_PATH, &dm_policy);
 
         let allow_from_json = serde_json::to_string(&config.allow_from.unwrap_or_default())
@@ -840,8 +844,8 @@ fn send_pairing_reply(chat_id: i64, code: &str) -> Result<(), String> {
         "parse_mode": "Markdown",
     });
 
-    let payload_bytes =
-        serde_json::to_vec(&payload).map_err(|e| format!("Failed to serialize payload: {}", e))?;
+    let payload_bytes = serde_json::to_vec(&payload)
+        .map_err(|e| format!("Failed to serialize payload: {}", e))?;
 
     let headers = serde_json::json!({
         "Content-Type": "application/json"
@@ -911,10 +915,15 @@ fn handle_message(message: TelegramMessage) {
     let is_private = message.chat.chat_type == "private";
 
     // Owner validation: when owner_id is set, only that user can message
-    let owner_id_str = channel_host::workspace_read(OWNER_ID_PATH).filter(|s| !s.is_empty());
+    let owner_configured = channel_host::workspace_read(OWNER_ID_PATH)
+        .map(|s| !s.is_empty())
+        .unwrap_or(false);
 
-    if let Some(ref id_str) = owner_id_str {
-        if let Ok(owner_id) = id_str.parse::<i64>() {
+    if owner_configured {
+        if let Ok(owner_id) = channel_host::workspace_read(OWNER_ID_PATH)
+            .unwrap()
+            .parse::<i64>()
+        {
             if from.id != owner_id {
                 channel_host::log(
                     channel_host::LogLevel::Debug,
@@ -928,8 +937,8 @@ fn handle_message(message: TelegramMessage) {
         }
     } else if is_private {
         // No owner_id: apply dm_policy for private chats
-        let dm_policy =
-            channel_host::workspace_read(DM_POLICY_PATH).unwrap_or_else(|| "pairing".to_string());
+        let dm_policy = channel_host::workspace_read(DM_POLICY_PATH)
+            .unwrap_or_else(|| "pairing".to_string());
 
         if dm_policy != "open" {
             // Build effective allow list: config allow_from + pairing store
@@ -992,7 +1001,8 @@ fn handle_message(message: TelegramMessage) {
 
         if !respond_to_all {
             let has_command = content.starts_with('/');
-            let bot_username = channel_host::workspace_read(BOT_USERNAME_PATH).unwrap_or_default();
+            let bot_username = channel_host::workspace_read(BOT_USERNAME_PATH)
+                .unwrap_or_default();
             let has_bot_mention = if bot_username.is_empty() {
                 content.contains('@')
             } else {

channels-src/whatsapp/src/lib.rs

@@ -254,19 +254,10 @@ struct WhatsAppChannel;
 
 impl Guest for WhatsAppChannel {
     fn on_start(config_json: String) -> Result<ChannelConfig, String> {
-        let config: WhatsAppConfig = match serde_json::from_str(&config_json) {
-            Ok(c) => c,
-            Err(e) => {
-                channel_host::log(
-                    channel_host::LogLevel::Warn,
-                    &format!("Failed to parse WhatsApp config, using defaults: {}", e),
-                );
-                WhatsAppConfig {
-                    api_version: default_api_version(),
-                    reply_to_message: default_reply_to_message(),
-                }
-            }
-        };
+        let config: WhatsAppConfig = serde_json::from_str(&config_json).unwrap_or(WhatsAppConfig {
+            api_version: default_api_version(),
+            reply_to_message: default_reply_to_message(),
+        });
 
         channel_host::log(
             channel_host::LogLevel::Info,
@@ -276,9 +267,6 @@ impl Guest for WhatsAppChannel {
             ),
         );
 
-        // Persist api_version in workspace so on_respond() can read it
-        let _ = channel_host::workspace_write("channels/whatsapp/api_version", &config.api_version);
-
         // WhatsApp Cloud API is webhook-only, no polling available
         Ok(ChannelConfig {
             display_name: "WhatsApp".to_string(),
@@ -339,16 +327,11 @@ impl Guest for WhatsAppChannel {
         let metadata: WhatsAppMessageMetadata = serde_json::from_str(&response.metadata_json)
             .map_err(|e| format!("Failed to parse metadata: {}", e))?;
 
-        // Read api_version from workspace (set during on_start), fallback to default
-        let api_version = channel_host::workspace_read("channels/whatsapp/api_version")
-            .filter(|s| !s.is_empty())
-            .unwrap_or_else(|| "v18.0".to_string());
-
         // Build WhatsApp API URL with token placeholder
         // Host will replace {WHATSAPP_ACCESS_TOKEN} with actual token in Authorization header
         let api_url = format!(
-            "https://graph.facebook.com/{}/{}/messages",
-            api_version, metadata.phone_number_id
+            "https://graph.facebook.com/v18.0/{}/messages",
+            metadata.phone_number_id
         );
 
         // Build sendMessage payload

deploy/cloud-sql-proxy.service

@@ -1,13 +0,0 @@
-[Unit]
-Description=Cloud SQL Auth Proxy
-After=network.target
-
-[Service]
-Type=simple
-DynamicUser=yes
-ExecStart=/usr/local/bin/cloud-sql-proxy ironclaw-prod:us-central1:ironclaw-db --port=5432
-Restart=always
-RestartSec=5
-
-[Install]
-WantedBy=multi-user.target

deploy/env.example

@@ -1,27 +0,0 @@
-# WARNING: Replace all CHANGE_ME values before deploying.
-# Do not use placeholder passwords in production.
-DATABASE_URL=postgres://ironclaw:CHANGE_ME@localhost:5432/ironclaw
-
-# NEAR AI
-NEARAI_SESSION_TOKEN=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
-
-# Agent
-AGENT_NAME=ironclaw
-CLI_ENABLED=false
-
-# Web Gateway
-GATEWAY_ENABLED=true
-# 0.0.0.0 binds to all interfaces (required for Docker --network=host).
-# Use 127.0.0.1 if running outside Docker or for local-only access.
-GATEWAY_HOST=0.0.0.0
-GATEWAY_PORT=3000
-GATEWAY_AUTH_TOKEN=CHANGE_ME
-
-# Disabled for initial deploy
-SANDBOX_ENABLED=false
-HEARTBEAT_ENABLED=false
-EMBEDDING_ENABLED=false

deploy/ironclaw.service

@@ -1,20 +0,0 @@
-[Unit]
-Description=IronClaw AI Assistant
-After=cloud-sql-proxy.service docker.service
-Requires=cloud-sql-proxy.service
-
-[Service]
-Type=simple
-ExecStartPre=/usr/bin/docker pull us-central1-docker.pkg.dev/ironclaw-prod/ironclaw/agent:latest
-ExecStart=/usr/bin/docker run --rm \
-  --name ironclaw \
-  --env-file /opt/ironclaw/.env \
-  --network=host \
-  us-central1-docker.pkg.dev/ironclaw-prod/ironclaw/agent:latest \
-  --no-onboard
-ExecStop=/usr/bin/docker stop ironclaw
-Restart=always
-RestartSec=10
-
-[Install]
-WantedBy=multi-user.target

deploy/setup.sh

@@ -1,68 +0,0 @@
-#!/usr/bin/env bash
-# VM bootstrap script for IronClaw on GCP Compute Engine.
-#
-# Run on a fresh Debian 12 VM after SSH:
-#   sudo bash setup.sh
-#
-# Prerequisites:
-#   - VM has the ironclaw-vm service account attached
-#   - Cloud SQL Auth Proxy accessible via IAM
-#   - Artifact Registry image pushed
-
-set -euo pipefail
-
-# Must run as root
-if [ "$(id -u)" -ne 0 ]; then
-  echo "ERROR: This script must be run as root (sudo bash setup.sh)"
-  exit 1
-fi
-
-echo "==> Installing Docker"
-apt-get update
-apt-get install -y docker.io
-systemctl enable docker
-systemctl start docker
-
-echo "==> Installing Cloud SQL Auth Proxy"
-curl -fsSL -o /usr/local/bin/cloud-sql-proxy \
-  https://storage.googleapis.com/cloud-sql-connectors/cloud-sql-proxy/v2.14.3/cloud-sql-proxy.linux.amd64
-chmod +x /usr/local/bin/cloud-sql-proxy
-
-echo "==> Installing systemd services"
-cp /tmp/deploy/cloud-sql-proxy.service /etc/systemd/system/
-cp /tmp/deploy/ironclaw.service /etc/systemd/system/
-systemctl daemon-reload
-
-echo "==> Starting Cloud SQL Auth Proxy"
-systemctl enable cloud-sql-proxy
-systemctl start cloud-sql-proxy
-
-echo "==> Configuring Docker registry auth"
-# The VM service account provides Artifact Registry access
-gcloud auth configure-docker us-central1-docker.pkg.dev --quiet
-
-echo "==> Creating config directory"
-# Owned by root, readable only by root. Docker reads --env-file as root
-# before dropping to uid 1000 (ironclaw) inside the container.
-mkdir -p /opt/ironclaw
-chmod 700 /opt/ironclaw
-
-if [ ! -f /opt/ironclaw/.env ]; then
-  echo "WARNING: /opt/ironclaw/.env does not exist."
-  echo "Create it with your configuration before starting IronClaw."
-  echo "See deploy/env.example for the required variables."
-  echo ""
-  echo "Then run: systemctl enable ironclaw && systemctl start ironclaw"
-else
-  chmod 600 /opt/ironclaw/.env
-  echo "==> Starting IronClaw"
-  systemctl enable ironclaw
-  systemctl start ironclaw
-fi
-
-echo "==> Setup complete"
-echo ""
-echo "Verify with:"
-echo "  systemctl status cloud-sql-proxy"
-echo "  systemctl status ironclaw"
-echo "  docker logs ironclaw"

examples/test_heartbeat.rs

@@ -81,6 +81,7 @@ async fn main() -> anyhow::Result<()> {
     let session = create_session_manager(SessionConfig {
         auth_base_url: config.llm.nearai.auth_base_url.clone(),
         session_path: config.llm.nearai.session_path.clone(),
+        ..Default::default()
     })
     .await;
     let llm = create_llm_provider(&config.llm, session)?;

src/agent/agent_loop.rs

@@ -22,14 +22,13 @@ use crate::context::JobContext;
 use crate::db::Database;
 use crate::error::Error;
 use crate::extensions::ExtensionManager;
-use crate::hooks::HookRegistry;
 use crate::llm::{ChatMessage, LlmProvider, Reasoning, ReasoningContext, RespondResult};
 use crate::safety::SafetyLayer;
 use crate::tools::ToolRegistry;
 use crate::workspace::Workspace;
 
 /// Collapse a tool output string into a single-line preview for display.
-pub(crate) fn truncate_for_preview(output: &str, max_chars: usize) -> String {
+fn truncate_for_preview(output: &str, max_chars: usize) -> String {
     let collapsed: String = output
         .chars()
         .take(max_chars + 50)
@@ -38,14 +37,8 @@ pub(crate) fn truncate_for_preview(output: &str, max_chars: usize) -> String {
         .split_whitespace()
         .collect::<Vec<_>>()
         .join(" ");
-    // char_indices gives us byte offsets at char boundaries, so the slice is always valid UTF-8.
-    if collapsed.chars().count() > max_chars {
-        let byte_offset = collapsed
-            .char_indices()
-            .nth(max_chars)
-            .map(|(i, _)| i)
-            .unwrap_or(collapsed.len());
-        format!("{}...", &collapsed[..byte_offset])
+    if collapsed.len() > max_chars {
+        format!("{}...", &collapsed[..max_chars])
     } else {
         collapsed
     }
@@ -68,14 +61,10 @@ enum AgenticLoopResult {
 pub struct AgentDeps {
     pub store: Option<Arc<dyn Database>>,
     pub llm: Arc<dyn LlmProvider>,
-    /// Cheap/fast LLM for lightweight tasks (heartbeat, routing, evaluation).
-    /// Falls back to the main `llm` if None.
-    pub cheap_llm: Option<Arc<dyn LlmProvider>>,
     pub safety: Arc<SafetyLayer>,
     pub tools: Arc<ToolRegistry>,
     pub workspace: Option<Arc<Workspace>>,
     pub extension_manager: Option<Arc<ExtensionManager>>,
-    pub hooks: Arc<HookRegistry>,
 }
 
 /// The main agent that coordinates all components.
@@ -118,7 +107,6 @@ impl Agent {
             deps.safety.clone(),
             deps.tools.clone(),
             deps.store.clone(),
-            deps.hooks.clone(),
         ));
 
         Self {
@@ -144,11 +132,6 @@ impl Agent {
         &self.deps.llm
     }
 
-    /// Get the cheap/fast LLM provider, falling back to the main one.
-    fn cheap_llm(&self) -> &Arc<dyn LlmProvider> {
-        self.deps.cheap_llm.as_ref().unwrap_or(&self.deps.llm)
-    }
-
     fn safety(&self) -> &Arc<SafetyLayer> {
         &self.deps.safety
     }
@@ -161,10 +144,6 @@ impl Agent {
         self.deps.workspace.as_ref()
     }
 
-    fn hooks(&self) -> &Arc<HookRegistry> {
-        &self.deps.hooks
-    }
-
     /// Run the agent main loop.
     pub async fn run(self) -> Result<(), Error> {
         // Start channels
@@ -316,7 +295,7 @@ impl Agent {
                     Some(spawn_heartbeat(
                         config,
                         workspace.clone(),
-                        self.cheap_llm().clone(),
+                        self.llm().clone(),
                         Some(notify_tx),
                     ))
                 } else {
@@ -432,32 +411,10 @@ impl Agent {
 
             match self.handle_message(&message).await {
                 Ok(Some(response)) if !response.is_empty() => {
-                    // Hook: BeforeOutbound — allow hooks to modify or suppress outbound
-                    let event = crate::hooks::HookEvent::Outbound {
-                        user_id: message.user_id.clone(),
-                        channel: message.channel.clone(),
-                        content: response.clone(),
-                        thread_id: message.thread_id.clone(),
-                    };
-                    match self.hooks().run(&event).await {
-                        Err(err) => {
-                            tracing::warn!("BeforeOutbound hook blocked response: {}", err);
-                        }
-                        Ok(crate::hooks::HookOutcome::Continue {
-                            modified: Some(new_content),
-                        }) => {
-                            let _ = self
-                                .channels
-                                .respond(&message, OutgoingResponse::text(new_content))
-                                .await;
-                        }
-                        _ => {
-                            let _ = self
-                                .channels
-                                .respond(&message, OutgoingResponse::text(response))
-                                .await;
-                        }
-                    }
+                    let _ = self
+                        .channels
+                        .respond(&message, OutgoingResponse::text(response))
+                        .await;
                 }
                 Ok(Some(_)) => {
                     // Empty response, nothing to send (e.g. approval handled via send_status)
@@ -503,33 +460,7 @@ impl Agent {
 
     async fn handle_message(&self, message: &IncomingMessage) -> Result<Option<String>, Error> {
         // Parse submission type first
-        let mut submission = SubmissionParser::parse(&message.content);
-
-        // Hook: BeforeInbound — allow hooks to modify or reject user input
-        if let Submission::UserInput { ref content } = submission {
-            let event = crate::hooks::HookEvent::Inbound {
-                user_id: message.user_id.clone(),
-                channel: message.channel.clone(),
-                content: content.clone(),
-                thread_id: message.thread_id.clone(),
-            };
-            match self.hooks().run(&event).await {
-                Err(crate::hooks::HookError::Rejected { reason }) => {
-                    return Ok(Some(format!("[Message rejected: {}]", reason)));
-                }
-                Err(err) => {
-                    return Ok(Some(format!("[Message blocked by hook policy: {}]", err)));
-                }
-                Ok(crate::hooks::HookOutcome::Continue {
-                    modified: Some(new_content),
-                }) => {
-                    submission = Submission::UserInput {
-                        content: new_content,
-                    };
-                }
-                _ => {} // Continue, fail-open errors already logged in registry
-            }
-        }
+        let submission = SubmissionParser::parse(&message.content);
 
         // Hydrate thread from DB if it's a historical thread not in memory
         if let Some(ref external_thread_id) = message.thread_id {
@@ -723,17 +654,19 @@ impl Agent {
         }
 
         // Restore response chain from conversation metadata
-        if let Some(store) = self.store()
-            && let Ok(Some(metadata)) = store.get_conversation_metadata(thread_uuid).await
-            && let Some(rid) = metadata
-                .get("last_response_id")
-                .and_then(|v| v.as_str())
-                .map(String::from)
-        {
-            thread.last_response_id = Some(rid.clone());
-            self.llm()
-                .seed_response_chain(&thread_uuid.to_string(), rid);
-            tracing::debug!("Restored response chain for thread {}", thread_uuid);
+        if let Some(store) = self.store() {
+            if let Ok(Some(metadata)) = store.get_conversation_metadata(thread_uuid).await {
+                if let Some(rid) = metadata
+                    .get("last_response_id")
+                    .and_then(|v| v.as_str())
+                    .map(String::from)
+                {
+                    thread.last_response_id = Some(rid.clone());
+                    self.llm()
+                        .seed_response_chain(&thread_uuid.to_string(), rid);
+                    tracing::debug!("Restored response chain for thread {}", thread_uuid);
+                }
+            }
         }
 
         // Insert into session and register with session manager
@@ -938,27 +871,6 @@ impl Agent {
         // Complete, fail, or request approval
         match result {
             Ok(AgenticLoopResult::Response(response)) => {
-                // Hook: TransformResponse — allow hooks to modify or reject the final response
-                let response = {
-                    let event = crate::hooks::HookEvent::ResponseTransform {
-                        user_id: message.user_id.clone(),
-                        thread_id: thread_id.to_string(),
-                        response: response.clone(),
-                    };
-                    match self.hooks().run(&event).await {
-                        Err(crate::hooks::HookError::Rejected { reason }) => {
-                            format!("[Response filtered: {}]", reason)
-                        }
-                        Err(err) => {
-                            format!("[Response blocked by hook policy: {}]", err)
-                        }
-                        Ok(crate::hooks::HookOutcome::Continue {
-                            modified: Some(new_response),
-                        }) => new_response,
-                        _ => response, // fail-open: use original
-                    }
-                };
-
                 thread.complete_turn(&response);
                 self.persist_response_chain(thread);
                 let _ = self
@@ -1042,12 +954,13 @@ impl Agent {
                 return;
             }
 
-            if let Some(ref resp) = response
-                && let Err(e) = store
+            if let Some(ref resp) = response {
+                if let Err(e) = store
                     .add_conversation_message(thread_id, "assistant", resp)
                     .await
-            {
-                tracing::warn!("Failed to persist assistant message: {}", e);
+                {
+                    tracing::warn!("Failed to persist assistant message: {}", e);
+                }
             }
         });
     }
@@ -1145,14 +1058,14 @@ impl Agent {
             // Check if interrupted
             {
                 let sess = session.lock().await;
-                if let Some(thread) = sess.threads.get(&thread_id)
-                    && thread.state == ThreadState::Interrupted
-                {
-                    return Err(crate::error::JobError::ContextError {
-                        id: thread_id,
-                        reason: "Interrupted".to_string(),
+                if let Some(thread) = sess.threads.get(&thread_id) {
+                    if thread.state == ThreadState::Interrupted {
+                        return Err(crate::error::JobError::ContextError {
+                            id: thread_id,
+                            reason: "Interrupted".to_string(),
+                        }
+                        .into());
                     }
-                    .into());
                 }
             }
 
@@ -1227,90 +1140,66 @@ impl Agent {
                     // Record tool calls in the thread
                     {
                         let mut sess = session.lock().await;
-                        if let Some(thread) = sess.threads.get_mut(&thread_id)
-                            && let Some(turn) = thread.last_turn_mut()
-                        {
-                            for tc in &tool_calls {
-                                turn.record_tool_call(&tc.name, tc.arguments.clone());
+                        if let Some(thread) = sess.threads.get_mut(&thread_id) {
+                            if let Some(turn) = thread.last_turn_mut() {
+                                for tc in &tool_calls {
+                                    turn.record_tool_call(&tc.name, tc.arguments.clone());
+                                }
                             }
                         }
                     }
 
-                    // Execute each tool (with approval checking and hook interception)
-                    for mut tc in tool_calls {
+                    // Execute each tool (with approval checking)
+                    for tc in tool_calls {
                         // Check if tool requires approval
-                        if let Some(tool) = self.tools().get(&tc.name).await
-                            && tool.requires_approval()
-                        {
-                            // Check if auto-approved for this session
-                            let mut is_auto_approved = {
-                                let sess = session.lock().await;
-                                sess.is_tool_auto_approved(&tc.name)
-                            };
-
-                            // Let the tool inspect the specific parameters and
-                            // override auto-approval (e.g. destructive shell commands).
-                            if is_auto_approved && tool.requires_approval_for(&tc.arguments) {
-                                tracing::info!(
-                                    tool = %tc.name,
-                                    "Tool requires explicit approval for these parameters despite auto-approve"
-                                );
-                                is_auto_approved = false;
-                            }
-
-                            if !is_auto_approved {
-                                // Need approval - store pending request and return
-                                let pending = PendingApproval {
-                                    request_id: Uuid::new_v4(),
-                                    tool_name: tc.name.clone(),
-                                    parameters: tc.arguments.clone(),
-                                    description: tool.description().to_string(),
-                                    tool_call_id: tc.id.clone(),
-                                    context_messages: context_messages.clone(),
+                        if let Some(tool) = self.tools().get(&tc.name).await {
+                            if tool.requires_approval() {
+                                // Check if auto-approved for this session
+                                let mut is_auto_approved = {
+                                    let sess = session.lock().await;
+                                    sess.is_tool_auto_approved(&tc.name)
                                 };
 
-                                return Ok(AgenticLoopResult::NeedApproval { pending });
-                            }
-                        }
-
-                        // Hook: BeforeToolCall — allow hooks to modify or reject tool calls
-                        {
-                            let event = crate::hooks::HookEvent::ToolCall {
-                                tool_name: tc.name.clone(),
-                                parameters: tc.arguments.clone(),
-                                user_id: message.user_id.clone(),
-                                context: "chat".to_string(),
-                            };
-                            match self.hooks().run(&event).await {
-                                Err(crate::hooks::HookError::Rejected { reason }) => {
-                                    context_messages.push(ChatMessage::tool_result(
-                                        &tc.id,
-                                        &tc.name,
-                                        format!("Tool call rejected by hook: {}", reason),
-                                    ));
-                                    continue;
-                                }
-                                Err(err) => {
-                                    context_messages.push(ChatMessage::tool_result(
-                                        &tc.id,
-                                        &tc.name,
-                                        format!("Tool call blocked by hook policy: {}", err),
-                                    ));
-                                    continue;
-                                }
-                                Ok(crate::hooks::HookOutcome::Continue {
-                                    modified: Some(new_params),
-                                }) => match serde_json::from_str(&new_params) {
-                                    Ok(parsed) => tc.arguments = parsed,
-                                    Err(e) => {
-                                        tracing::warn!(
-                                            tool = %tc.name,
-                                            "Hook returned non-JSON modification for ToolCall, ignoring: {}",
-                                            e
-                                        );
+                                // For shell commands, override auto-approval for
+                                // destructive patterns that should always require
+                                // explicit per-invocation approval.
+                                if is_auto_approved && tc.name == "shell" {
+                                    if let Some(cmd) = tc
+                                        .arguments
+                                        .as_str()
+                                        .and_then(|s| {
+                                            serde_json::from_str::<serde_json::Value>(s).ok()
+                                        })
+                                        .and_then(|v| {
+                                            v.get("command")
+                                                .and_then(|c| c.as_str().map(String::from))
+                                        })
+                                    {
+                                        if crate::tools::builtin::shell::requires_explicit_approval(
+                                            &cmd,
+                                        ) {
+                                            tracing::info!(
+                                                "Shell command '{}' requires explicit approval despite auto-approve",
+                                                cmd.chars().take(80).collect::<String>()
+                                            );
+                                            is_auto_approved = false;
+                                        }
                                     }
-                                },
-                                _ => {} // Continue, fail-open errors already logged
+                                }
+
+                                if !is_auto_approved {
+                                    // Need approval - store pending request and return
+                                    let pending = PendingApproval {
+                                        request_id: Uuid::new_v4(),
+                                        tool_name: tc.name.clone(),
+                                        parameters: tc.arguments.clone(),
+                                        description: tool.description().to_string(),
+                                        tool_call_id: tc.id.clone(),
+                                        context_messages: context_messages.clone(),
+                                    };
+
+                                    return Ok(AgenticLoopResult::NeedApproval { pending });
+                                }
                             }
                         }
 
@@ -1341,34 +1230,34 @@ impl Agent {
                             )
                             .await;
 
-                        if let Ok(ref output) = tool_result
-                            && !output.is_empty()
-                        {
-                            let _ = self
-                                .channels
-                                .send_status(
-                                    &message.channel,
-                                    StatusUpdate::ToolResult {
-                                        name: tc.name.clone(),
-                                        preview: output.clone(),
-                                    },
-                                    &message.metadata,
-                                )
-                                .await;
+                        if let Ok(ref output) = tool_result {
+                            if !output.is_empty() {
+                                let _ = self
+                                    .channels
+                                    .send_status(
+                                        &message.channel,
+                                        StatusUpdate::ToolResult {
+                                            name: tc.name.clone(),
+                                            preview: truncate_for_preview(output, 200),
+                                        },
+                                        &message.metadata,
+                                    )
+                                    .await;
+                            }
                         }
 
                         // Record result in thread
                         {
                             let mut sess = session.lock().await;
-                            if let Some(thread) = sess.threads.get_mut(&thread_id)
-                                && let Some(turn) = thread.last_turn_mut()
-                            {
-                                match &tool_result {
-                                    Ok(output) => {
-                                        turn.record_tool_result(serde_json::json!(output));
-                                    }
-                                    Err(e) => {
-                                        turn.record_tool_error(e.to_string());
+                            if let Some(thread) = sess.threads.get_mut(&thread_id) {
+                                if let Some(turn) = thread.last_turn_mut() {
+                                    match &tool_result {
+                                        Ok(output) => {
+                                            turn.record_tool_result(serde_json::json!(output));
+                                        }
+                                        Err(e) => {
+                                            turn.record_tool_error(e.to_string());
+                                        }
                                     }
                                 }
                             }
@@ -1579,9 +1468,6 @@ impl Agent {
         session: Arc<Mutex<Session>>,
         thread_id: Uuid,
     ) -> Result<SubmissionResult, Error> {
-        // Lock session first, then undo manager -- consistent with process_user_input
-        // to avoid potential deadlocks.
-        let mut sess = session.lock().await;
         let undo_mgr = self.session_manager.get_undo_manager(thread_id).await;
         let mut mgr = undo_mgr.lock().await;
 
@@ -1589,6 +1475,7 @@ impl Agent {
             return Ok(SubmissionResult::ok_with_message("Nothing to undo."));
         }
 
+        let mut sess = session.lock().await;
         let thread = sess
             .threads
             .get_mut(&thread_id)
@@ -1599,10 +1486,12 @@ impl Agent {
         let current_turn = thread.turn_number();
 
         if let Some(checkpoint) = mgr.undo(current_turn, current_messages) {
+            // Extract values before consuming the reference
             let turn_number = checkpoint.turn_number;
+            let messages = checkpoint.messages.clone();
             let undo_count = mgr.undo_count();
             // Restore thread from checkpoint
-            thread.restore_from_messages(checkpoint.messages);
+            thread.restore_from_messages(messages);
             Ok(SubmissionResult::ok_with_message(format!(
                 "Undone to turn {}. {} undo(s) remaining.",
                 turn_number, undo_count
@@ -1617,9 +1506,6 @@ impl Agent {
         session: Arc<Mutex<Session>>,
         thread_id: Uuid,
     ) -> Result<SubmissionResult, Error> {
-        // Lock session first, then undo manager -- consistent with process_user_input
-        // to avoid potential deadlocks.
-        let mut sess = session.lock().await;
         let undo_mgr = self.session_manager.get_undo_manager(thread_id).await;
         let mut mgr = undo_mgr.lock().await;
 
@@ -1627,15 +1513,12 @@ impl Agent {
             return Ok(SubmissionResult::ok_with_message("Nothing to redo."));
         }
 
-        let thread = sess
-            .threads
-            .get_mut(&thread_id)
-            .ok_or_else(|| Error::from(crate::error::JobError::NotFound { id: thread_id }))?;
-
-        let current_messages = thread.messages();
-        let current_turn = thread.turn_number();
-
-        if let Some(checkpoint) = mgr.redo(current_turn, current_messages) {
+        if let Some(checkpoint) = mgr.redo() {
+            let mut sess = session.lock().await;
+            let thread = sess
+                .threads
+                .get_mut(&thread_id)
+                .ok_or_else(|| Error::from(crate::error::JobError::NotFound { id: thread_id }))?;
             thread.restore_from_messages(checkpoint.messages);
             Ok(SubmissionResult::ok_with_message(format!(
                 "Redone to turn {}.",
@@ -1757,17 +1640,17 @@ impl Agent {
         };
 
         // Verify request ID if provided
-        if let Some(req_id) = request_id
-            && req_id != pending.request_id
-        {
-            // Put it back and return error
-            let mut sess = session.lock().await;
-            if let Some(thread) = sess.threads.get_mut(&thread_id) {
-                thread.await_approval(pending);
+        if let Some(req_id) = request_id {
+            if req_id != pending.request_id {
+                // Put it back and return error
+                let mut sess = session.lock().await;
+                if let Some(thread) = sess.threads.get_mut(&thread_id) {
+                    thread.await_approval(pending);
+                }
+                return Ok(SubmissionResult::error(
+                    "Request ID mismatch. Use the correct request ID.",
+                ));
             }
-            return Ok(SubmissionResult::error(
-                "Request ID mismatch. Use the correct request ID.",
-            ));
         }
 
         if approved {
@@ -1821,20 +1704,20 @@ impl Agent {
                 )
                 .await;
 
-            if let Ok(ref output) = tool_result
-                && !output.is_empty()
-            {
-                let _ = self
-                    .channels
-                    .send_status(
-                        &message.channel,
-                        StatusUpdate::ToolResult {
-                            name: pending.tool_name.clone(),
-                            preview: output.clone(),
-                        },
-                        &message.metadata,
-                    )
-                    .await;
+            if let Ok(ref output) = tool_result {
+                if !output.is_empty() {
+                    let _ = self
+                        .channels
+                        .send_status(
+                            &message.channel,
+                            StatusUpdate::ToolResult {
+                                name: pending.tool_name.clone(),
+                                preview: truncate_for_preview(output, 200),
+                            },
+                            &message.metadata,
+                        )
+                        .await;
+                }
             }
 
             // Build context including the tool result
@@ -1843,15 +1726,15 @@ impl Agent {
             // Record result in thread
             {
                 let mut sess = session.lock().await;
-                if let Some(thread) = sess.threads.get_mut(&thread_id)
-                    && let Some(turn) = thread.last_turn_mut()
-                {
-                    match &tool_result {
-                        Ok(output) => {
-                            turn.record_tool_result(serde_json::json!(output));
-                        }
-                        Err(e) => {
-                            turn.record_tool_error(e.to_string());
+                if let Some(thread) = sess.threads.get_mut(&thread_id) {
+                    if let Some(turn) = thread.last_turn_mut() {
+                        match &tool_result {
+                            Ok(output) => {
+                                turn.record_tool_result(serde_json::json!(output));
+                            }
+                            Err(e) => {
+                                turn.record_tool_error(e.to_string());
+                            }
                         }
                     }
                 }
@@ -2211,15 +2094,15 @@ impl Agent {
         }
 
         // 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);
-                }
-            });
+        if let Some(store) = self.store() {
+            if 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
@@ -2299,10 +2182,10 @@ impl Agent {
 
         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));
+            if let Ok(ctx) = self.context_manager.get_context(job_id).await {
+                if ctx.user_id == user_id {
+                    output.push_str(&format!("  {} - {} ({:?})\n", job_id, ctx.title, ctx.state));
+                }
             }
         }
 
@@ -2753,70 +2636,4 @@ mod tests {
 
         assert!(detect_auth_awaiting("tool_activate", &result).is_none());
     }
-
-    // --- truncate_for_preview tests ---
-
-    use super::truncate_for_preview;
-
-    #[test]
-    fn test_truncate_short_input() {
-        assert_eq!(truncate_for_preview("hello", 10), "hello");
-    }
-
-    #[test]
-    fn test_truncate_empty_input() {
-        assert_eq!(truncate_for_preview("", 10), "");
-    }
-
-    #[test]
-    fn test_truncate_exact_length() {
-        assert_eq!(truncate_for_preview("hello", 5), "hello");
-    }
-
-    #[test]
-    fn test_truncate_over_limit() {
-        let result = truncate_for_preview("hello world, this is long", 10);
-        assert!(result.ends_with("..."));
-        // "hello worl" = 10 chars + "..."
-        assert_eq!(result, "hello worl...");
-    }
-
-    #[test]
-    fn test_truncate_collapses_newlines() {
-        let result = truncate_for_preview("line1\nline2\nline3", 100);
-        assert!(!result.contains('\n'));
-        assert_eq!(result, "line1 line2 line3");
-    }
-
-    #[test]
-    fn test_truncate_collapses_whitespace() {
-        let result = truncate_for_preview("hello   world", 100);
-        assert_eq!(result, "hello world");
-    }
-
-    #[test]
-    fn test_truncate_multibyte_utf8() {
-        // Each emoji is 4 bytes. Truncating at char boundary must not panic.
-        let input = "😀😁😂🤣😃😄😅😆😉😊";
-        let result = truncate_for_preview(input, 5);
-        assert!(result.ends_with("..."));
-        // First 5 chars = 5 emoji
-        assert_eq!(result, "😀😁😂🤣😃...");
-    }
-
-    #[test]
-    fn test_truncate_cjk_characters() {
-        // CJK chars are 3 bytes each in UTF-8.
-        let input = "你好世界测试数据很长的字符串";
-        let result = truncate_for_preview(input, 4);
-        assert_eq!(result, "你好世界...");
-    }
-
-    #[test]
-    fn test_truncate_mixed_multibyte_and_ascii() {
-        let input = "hello 世界 foo";
-        let result = truncate_for_preview(input, 8);
-        // 'h','e','l','l','o',' ','世','界' = 8 chars
-        assert_eq!(result, "hello 世界...");
-    }
 }

src/agent/mod.rs

@@ -26,7 +26,6 @@ pub mod task;
 pub mod undo;
 pub mod worker;
 
-pub(crate) use agent_loop::truncate_for_preview;
 pub use agent_loop::{Agent, AgentDeps};
 pub use compaction::{CompactionResult, ContextCompactor};
 pub use context_monitor::{CompactionStrategy, ContextBreakdown, ContextMonitor};

src/agent/routine_engine.rs

@@ -103,9 +103,10 @@ impl RoutineEngine {
             if let Trigger::Event {
                 channel: Some(ch), ..
             } = &routine.trigger
-                && ch != &message.channel
             {
-                continue;
+                if ch != &message.channel {
+                    continue;
+                }
             }
 
             // Regex match

src/agent/scheduler.rs

@@ -14,7 +14,6 @@ use crate::config::AgentConfig;
 use crate::context::{ContextManager, JobContext, JobState};
 use crate::db::Database;
 use crate::error::{Error, JobError};
-use crate::hooks::HookRegistry;
 use crate::llm::LlmProvider;
 use crate::safety::SafetyLayer;
 use crate::tools::ToolRegistry;
@@ -50,7 +49,6 @@ pub struct Scheduler {
     safety: Arc<SafetyLayer>,
     tools: Arc<ToolRegistry>,
     store: Option<Arc<dyn Database>>,
-    hooks: Arc<HookRegistry>,
     /// Running jobs (main LLM-driven jobs).
     jobs: Arc<RwLock<HashMap<Uuid, ScheduledJob>>>,
     /// Running sub-tasks (tool executions, background tasks).
@@ -66,7 +64,6 @@ impl Scheduler {
         safety: Arc<SafetyLayer>,
         tools: Arc<ToolRegistry>,
         store: Option<Arc<dyn Database>>,
-        hooks: Arc<HookRegistry>,
     ) -> Self {
         Self {
             config,
@@ -75,7 +72,6 @@ impl Scheduler {
             safety,
             tools,
             store,
-            hooks,
             jobs: Arc::new(RwLock::new(HashMap::new())),
             subtasks: Arc::new(RwLock::new(HashMap::new())),
         }
@@ -122,7 +118,6 @@ impl Scheduler {
                 safety: self.safety.clone(),
                 tools: self.tools.clone(),
                 store: self.store.clone(),
-                hooks: self.hooks.clone(),
                 timeout: self.config.job_timeout,
                 use_planning: self.config.use_planning,
             };

src/agent/self_repair.rs

@@ -119,25 +119,25 @@ impl SelfRepair for DefaultSelfRepair {
         let mut stuck_jobs = Vec::new();
 
         for job_id in stuck_ids {
-            if let Ok(ctx) = self.context_manager.get_context(job_id).await
-                && ctx.state == JobState::Stuck
-            {
-                let stuck_duration = ctx
-                    .started_at
-                    .map(|start| {
-                        let now = Utc::now();
-                        let duration = now.signed_duration_since(start);
-                        Duration::from_secs(duration.num_seconds().max(0) as u64)
-                    })
-                    .unwrap_or_default();
+            if let Ok(ctx) = self.context_manager.get_context(job_id).await {
+                if ctx.state == JobState::Stuck {
+                    let stuck_duration = ctx
+                        .started_at
+                        .map(|start| {
+                            let now = Utc::now();
+                            let duration = now.signed_duration_since(start);
+                            Duration::from_secs(duration.num_seconds().max(0) as u64)
+                        })
+                        .unwrap_or_default();
 
-                stuck_jobs.push(StuckJob {
-                    job_id,
-                    last_activity: ctx.started_at.unwrap_or(ctx.created_at),
-                    stuck_duration,
-                    last_error: None,
-                    repair_attempts: ctx.repair_attempts,
-                });
+                    stuck_jobs.push(StuckJob {
+                        job_id,
+                        last_activity: ctx.started_at.unwrap_or(ctx.created_at),
+                        stuck_duration,
+                        last_error: None,
+                        repair_attempts: ctx.repair_attempts,
+                    });
+                }
             }
         }
 

src/agent/session.rs

@@ -346,11 +346,11 @@ impl Thread {
                 let mut turn = Turn::new(turn_number, &msg.content);
 
                 // Check if next is assistant response
-                if let Some(next) = iter.peek()
-                    && next.role == crate::llm::Role::Assistant
-                {
-                    let response = iter.next().expect("peeked");
-                    turn.complete(&response.content);
+                if let Some(next) = iter.peek() {
+                    if next.role == crate::llm::Role::Assistant {
+                        let response = iter.next().expect("peeked");
+                        turn.complete(&response.content);
+                    }
                 }
 
                 self.turns.push(turn);

src/agent/session_manager.rs

@@ -11,7 +11,6 @@ use uuid::Uuid;
 
 use crate::agent::session::Session;
 use crate::agent::undo::UndoManager;
-use crate::hooks::HookRegistry;
 
 /// Key for mapping external thread IDs to internal ones.
 #[derive(Clone, Hash, Eq, PartialEq)]
@@ -26,7 +25,6 @@ pub struct SessionManager {
     sessions: RwLock<HashMap<String, Arc<Mutex<Session>>>>,
     thread_map: RwLock<HashMap<ThreadKey, Uuid>>,
     undo_managers: RwLock<HashMap<Uuid, Arc<Mutex<UndoManager>>>>,
-    hooks: Option<Arc<HookRegistry>>,
 }
 
 impl SessionManager {
@@ -36,16 +34,9 @@ impl SessionManager {
             sessions: RwLock::new(HashMap::new()),
             thread_map: RwLock::new(HashMap::new()),
             undo_managers: RwLock::new(HashMap::new()),
-            hooks: None,
         }
     }
 
-    /// Attach a hook registry for session lifecycle events.
-    pub fn with_hooks(mut self, hooks: Arc<HookRegistry>) -> Self {
-        self.hooks = Some(hooks);
-        self
-    }
-
     /// Get or create a session for a user.
     pub async fn get_or_create_session(&self, user_id: &str) -> Arc<Mutex<Session>> {
         // Fast path: check if session exists
@@ -63,28 +54,8 @@ impl SessionManager {
             return Arc::clone(session);
         }
 
-        let new_session = Session::new(user_id);
-        let session_id = new_session.id.to_string();
-        let session = Arc::new(Mutex::new(new_session));
+        let session = Arc::new(Mutex::new(Session::new(user_id)));
         sessions.insert(user_id.to_string(), Arc::clone(&session));
-
-        // Fire OnSessionStart hook (fire-and-forget)
-        if let Some(ref hooks) = self.hooks {
-            let hooks = hooks.clone();
-            let uid = user_id.to_string();
-            let sid = session_id;
-            tokio::spawn(async move {
-                use crate::hooks::HookEvent;
-                let event = HookEvent::SessionStart {
-                    user_id: uid,
-                    session_id: sid,
-                };
-                if let Err(e) = hooks.run(&event).await {
-                    tracing::warn!("OnSessionStart hook error: {}", e);
-                }
-            });
-        }
-
         session
     }
 
@@ -202,8 +173,8 @@ impl SessionManager {
     pub async fn prune_stale_sessions(&self, max_idle: std::time::Duration) -> usize {
         let cutoff = chrono::Utc::now() - chrono::TimeDelta::seconds(max_idle.as_secs() as i64);
 
-        // Find stale sessions (user_id + session_id)
-        let stale_sessions: Vec<(String, String)> = {
+        // Find stale session user_ids
+        let stale_users: Vec<String> = {
             let sessions = self.sessions.read().await;
             sessions
                 .iter()
@@ -211,7 +182,7 @@ impl SessionManager {
                     // Try to lock; skip if contended (someone is actively using it)
                     let sess = session.try_lock().ok()?;
                     if sess.last_active_at < cutoff {
-                        Some((user_id.clone(), sess.id.to_string()))
+                        Some(user_id.clone())
                     } else {
                         None
                     }
@@ -219,11 +190,6 @@ impl SessionManager {
                 .collect()
         };
 
-        let stale_users: Vec<String> = stale_sessions
-            .iter()
-            .map(|(user_id, _)| user_id.clone())
-            .collect();
-
         if stale_users.is_empty() {
             return 0;
         }
@@ -233,30 +199,11 @@ impl SessionManager {
         {
             let sessions = self.sessions.read().await;
             for user_id in &stale_users {
-                if let Some(session) = sessions.get(user_id)
-                    && let Ok(sess) = session.try_lock()
-                {
-                    stale_thread_ids.extend(sess.threads.keys());
-                }
-            }
-        }
-
-        // Fire OnSessionEnd hooks for stale sessions (fire-and-forget)
-        if let Some(ref hooks) = self.hooks {
-            for (user_id, session_id) in &stale_sessions {
-                let hooks = hooks.clone();
-                let uid = user_id.clone();
-                let sid = session_id.clone();
-                tokio::spawn(async move {
-                    use crate::hooks::HookEvent;
-                    let event = HookEvent::SessionEnd {
-                        user_id: uid,
-                        session_id: sid,
-                    };
-                    if let Err(e) = hooks.run(&event).await {
-                        tracing::warn!("OnSessionEnd hook error: {}", e);
+                if let Some(session) = sessions.get(user_id) {
+                    if let Ok(sess) = session.try_lock() {
+                        stale_thread_ids.extend(sess.threads.keys());
                     }
-                });
+                }
             }
         }
 

src/agent/submission.rs

@@ -93,26 +93,27 @@ impl SubmissionParser {
         // /thread <uuid> - switch thread
         if let Some(rest) = lower.strip_prefix("/thread ") {
             let rest = rest.trim();
-            if rest != "new"
-                && let Ok(id) = Uuid::parse_str(rest)
-            {
-                return Submission::SwitchThread { thread_id: id };
+            if rest != "new" {
+                if let Ok(id) = Uuid::parse_str(rest) {
+                    return Submission::SwitchThread { thread_id: id };
+                }
             }
         }
 
         // /resume <uuid> - resume from checkpoint
-        if let Some(rest) = lower.strip_prefix("/resume ")
-            && let Ok(id) = Uuid::parse_str(rest.trim())
-        {
-            return Submission::Resume { checkpoint_id: id };
+        if let Some(rest) = lower.strip_prefix("/resume ") {
+            if let Ok(id) = Uuid::parse_str(rest.trim()) {
+                return Submission::Resume { checkpoint_id: id };
+            }
         }
 
         // Try structured JSON approval (from web gateway's /api/chat/approval endpoint)
-        if trimmed.starts_with('{')
-            && let Ok(submission) = serde_json::from_str::<Submission>(trimmed)
-            && matches!(submission, Submission::ExecApproval { .. })
-        {
-            return submission;
+        if trimmed.starts_with('{') {
+            if let Ok(submission) = serde_json::from_str::<Submission>(trimmed) {
+                if matches!(submission, Submission::ExecApproval { .. }) {
+                    return submission;
+                }
+            }
         }
 
         // Approval responses (simple yes/no/always for pending approvals)

src/agent/undo.rs

@@ -43,10 +43,6 @@ 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>,
@@ -72,14 +68,6 @@ impl UndoManager {
         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.
@@ -92,23 +80,24 @@ 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.push_undo(checkpoint);
+        self.undo_stack.push_back(checkpoint);
+
+        // Trim if over limit
+        while self.undo_stack.len() > self.max_checkpoints {
+            self.undo_stack.pop_front();
+        }
     }
 
     /// Undo: pop the last checkpoint and return it.
     ///
-    /// 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.
+    /// The current state should be saved to redo stack before calling this.
     pub fn undo(
         &mut self,
         current_turn: usize,
         current_messages: Vec<ChatMessage>,
-    ) -> Option<Checkpoint> {
+    ) -> Option<&Checkpoint> {
         if self.undo_stack.is_empty() {
             return None;
         }
@@ -121,8 +110,9 @@ impl UndoManager {
         );
         self.redo_stack.push(current);
 
-        // Pop and return the most recent checkpoint
-        self.undo_stack.pop_back()
+        // Return the most recent checkpoint without removing it
+        // (we keep it so multiple undos can work)
+        self.undo_stack.back()
     }
 
     /// Pop the last checkpoint from the undo stack.
@@ -131,29 +121,7 @@ impl UndoManager {
     }
 
     /// Redo: restore a previously undone state.
-    ///
-    /// 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);
-
+    pub fn redo(&mut self) -> Option<Checkpoint> {
         self.redo_stack.pop()
     }
 
@@ -246,16 +214,14 @@ mod tests {
         assert!(manager.can_undo());
         assert!(!manager.can_redo());
 
-        // Undo - returns owned Checkpoint now
+        // Undo
         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 - now requires current state parameters
-        let restored = manager.redo(checkpoint.turn_number, checkpoint.messages);
+        // Redo
+        let restored = manager.redo();
         assert!(restored.is_some());
     }
 
@@ -283,90 +249,4 @@ 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

@@ -12,7 +12,6 @@ use crate::agent::task::TaskOutput;
 use crate::context::{ContextManager, JobState};
 use crate::db::Database;
 use crate::error::Error;
-use crate::hooks::HookRegistry;
 use crate::llm::{
     ActionPlan, ChatMessage, LlmProvider, Reasoning, ReasoningContext, RespondResult, ToolSelection,
 };
@@ -30,7 +29,6 @@ pub struct WorkerDeps {
     pub safety: Arc<SafetyLayer>,
     pub tools: Arc<ToolRegistry>,
     pub store: Option<Arc<dyn Database>>,
-    pub hooks: Arc<HookRegistry>,
     pub timeout: Duration,
     pub use_planning: bool,
 }
@@ -229,11 +227,11 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
             }
 
             // Check for cancellation
-            if let Ok(ctx) = self.context_manager().get_context(self.job_id).await
-                && ctx.state == JobState::Cancelled
-            {
-                tracing::info!("Worker for job {} detected cancellation", self.job_id);
-                return Ok(());
+            if let Ok(ctx) = self.context_manager().get_context(self.job_id).await {
+                if ctx.state == JobState::Cancelled {
+                    tracing::info!("Worker for job {} detected cancellation", self.job_id);
+                    return Ok(());
+                }
             }
 
             iteration += 1;
@@ -301,7 +299,6 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
                                 parameters: tc.arguments.clone(),
                                 reasoning: String::new(),
                                 alternatives: vec![],
-                                tool_call_id: tc.id.clone(),
                             };
 
                             self.process_tool_result(reason_ctx, &selection, result)
@@ -354,11 +351,23 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
             .map(|selection| {
                 let tool_name = selection.tool_name.clone();
                 let params = selection.parameters.clone();
-                let deps = self.deps.clone();
+                let tools = self.tools().clone();
+                let context_manager = self.context_manager().clone();
+                let safety = self.safety().clone();
                 let job_id = self.job_id;
+                let store = self.deps.store.clone();
 
                 async move {
-                    let result = Self::execute_tool_inner(&deps, job_id, &tool_name, &params).await;
+                    let result = Self::execute_tool_inner(
+                        tools,
+                        context_manager,
+                        safety,
+                        store,
+                        job_id,
+                        &tool_name,
+                        &params,
+                    )
+                    .await;
                     ToolExecResult { result }
                 }
             })
@@ -369,18 +378,20 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
 
     /// Inner tool execution logic that can be called from both single and parallel paths.
     async fn execute_tool_inner(
-        deps: &WorkerDeps,
+        tools: Arc<ToolRegistry>,
+        context_manager: Arc<ContextManager>,
+        safety: Arc<SafetyLayer>,
+        store: Option<Arc<dyn Database>>,
         job_id: Uuid,
         tool_name: &str,
         params: &serde_json::Value,
     ) -> Result<String, Error> {
-        let tool =
-            deps.tools
-                .get(tool_name)
-                .await
-                .ok_or_else(|| crate::error::ToolError::NotFound {
-                    name: tool_name.to_string(),
-                })?;
+        let tool = tools
+            .get(tool_name)
+            .await
+            .ok_or_else(|| crate::error::ToolError::NotFound {
+                name: tool_name.to_string(),
+            })?;
 
         // Tools requiring approval are blocked in autonomous jobs
         if tool.requires_approval() {
@@ -390,46 +401,8 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
             .into());
         }
 
-        // Fetch job context early so we have the real user_id for hooks
-        let job_ctx = deps.context_manager.get_context(job_id).await?;
-
-        // Run BeforeToolCall hook
-        let params = {
-            use crate::hooks::{HookError, HookEvent, HookOutcome};
-            let event = HookEvent::ToolCall {
-                tool_name: tool_name.to_string(),
-                parameters: params.clone(),
-                user_id: job_ctx.user_id.clone(),
-                context: format!("job:{}", job_id),
-            };
-            match deps.hooks.run(&event).await {
-                Err(HookError::Rejected { reason }) => {
-                    return Err(crate::error::ToolError::ExecutionFailed {
-                        name: tool_name.to_string(),
-                        reason: format!("Blocked by hook: {}", reason),
-                    }
-                    .into());
-                }
-                Err(err) => {
-                    return Err(crate::error::ToolError::ExecutionFailed {
-                        name: tool_name.to_string(),
-                        reason: format!("Blocked by hook failure mode: {}", err),
-                    }
-                    .into());
-                }
-                Ok(HookOutcome::Continue {
-                    modified: Some(new_params),
-                }) => serde_json::from_str(&new_params).unwrap_or_else(|e| {
-                    tracing::warn!(
-                        tool = %tool_name,
-                        "Hook returned non-JSON modification for ToolCall, ignoring: {}",
-                        e
-                    );
-                    params.clone()
-                }),
-                _ => params.clone(),
-            }
-        };
+        // Get job context for the tool
+        let job_ctx = context_manager.get_context(job_id).await?;
         if job_ctx.state == JobState::Cancelled {
             return Err(crate::error::ToolError::ExecutionFailed {
                 name: tool_name.to_string(),
@@ -439,7 +412,7 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
         }
 
         // Validate tool parameters
-        let validation = deps.safety.validator().validate_tool_params(&params);
+        let validation = safety.validator().validate_tool_params(params);
         if !validation.is_valid {
             let details = validation
                 .errors
@@ -504,8 +477,8 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
             Ok(Ok(output)) => {
                 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
+                    .map(|s| safety.sanitize_tool_output(tool_name, &s).content);
+                context_manager
                     .update_memory(job_id, |mem| {
                         let rec = mem.create_action(tool_name, params.clone()).succeed(
                             output_str.clone(),
@@ -518,8 +491,7 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
                     .await
                     .ok()
             }
-            Ok(Err(e)) => deps
-                .context_manager
+            Ok(Err(e)) => context_manager
                 .update_memory(job_id, |mem| {
                     let rec = mem
                         .create_action(tool_name, params.clone())
@@ -529,8 +501,7 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
                 })
                 .await
                 .ok(),
-            Err(_) => deps
-                .context_manager
+            Err(_) => context_manager
                 .update_memory(job_id, |mem| {
                     let rec = mem
                         .create_action(tool_name, params.clone())
@@ -543,7 +514,7 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
         };
 
         // Persist action to database (fire-and-forget)
-        if let (Some(action), Some(store)) = (action, deps.store.clone()) {
+        if let (Some(action), Some(store)) = (action, store) {
             tokio::spawn(async move {
                 if let Err(e) = store.save_action(job_id, &action).await {
                     tracing::warn!("Failed to persist action for job {}: {}", job_id, e);
@@ -594,7 +565,7 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
                 );
 
                 reason_ctx.messages.push(ChatMessage::tool_result(
-                    &selection.tool_call_id,
+                    "tool_call_id",
                     &selection.tool_name,
                     wrapped,
                 ));
@@ -626,7 +597,7 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
                 }
 
                 reason_ctx.messages.push(ChatMessage::tool_result(
-                    &selection.tool_call_id,
+                    "tool_call_id",
                     &selection.tool_name,
                     format!("Error: {}", e),
                 ));
@@ -676,15 +647,12 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
                 .execute_tool(&action.tool_name, &action.parameters)
                 .await;
 
-            // Create a synthetic ToolSelection for process_tool_result.
-            // Plan actions don't originate from an LLM tool_call response so
-            // there is no real tool_call_id; generate a unique one.
+            // Create a synthetic ToolSelection for process_tool_result
             let selection = ToolSelection {
                 tool_name: action.tool_name.clone(),
                 parameters: action.parameters.clone(),
                 reasoning: action.reasoning.clone(),
                 alternatives: vec![],
-                tool_call_id: format!("plan_{}_{}", self.job_id, i),
             };
 
             // Process the result
@@ -729,7 +697,16 @@ Report when the job is complete or if you encounter issues you cannot resolve."#
         tool_name: &str,
         params: &serde_json::Value,
     ) -> Result<String, Error> {
-        Self::execute_tool_inner(&self.deps, self.job_id, tool_name, params).await
+        Self::execute_tool_inner(
+            self.tools().clone(),
+            self.context_manager().clone(),
+            self.safety().clone(),
+            self.deps.store.clone(),
+            self.job_id,
+            tool_name,
+            params,
+        )
+        .await
     }
 
     async fn mark_completed(&self) -> Result<(), Error> {
@@ -797,26 +774,8 @@ impl From<TaskOutput> for Result<String, Error> {
 
 #[cfg(test)]
 mod tests {
-    use crate::llm::ToolSelection;
     use crate::util::llm_signals_completion;
 
-    #[test]
-    fn test_tool_selection_preserves_call_id() {
-        let selection = ToolSelection {
-            tool_name: "memory_search".to_string(),
-            parameters: serde_json::json!({"query": "test"}),
-            reasoning: "Need to search memory".to_string(),
-            alternatives: vec![],
-            tool_call_id: "call_abc123".to_string(),
-        };
-
-        assert_eq!(selection.tool_call_id, "call_abc123");
-        assert_ne!(
-            selection.tool_call_id, "tool_call_id",
-            "tool_call_id must not be the hardcoded placeholder string"
-        );
-    }
-
     #[test]
     fn test_completion_positive_signals() {
         assert!(llm_signals_completion("The job is complete."));

src/boot_screen.rs

@@ -1,208 +0,0 @@
-//! Boot screen displayed after all initialization completes.
-//!
-//! Shows a polished ANSI-styled status panel summarizing the agent's runtime
-//! state: model, database, tool count, enabled features, active channels,
-//! and the gateway URL.
-
-/// All displayable fields for the boot screen.
-pub struct BootInfo {
-    pub version: String,
-    pub agent_name: String,
-    pub llm_backend: String,
-    pub llm_model: String,
-    pub cheap_model: Option<String>,
-    pub db_backend: String,
-    pub db_connected: bool,
-    pub tool_count: usize,
-    pub gateway_url: Option<String>,
-    pub embeddings_enabled: bool,
-    pub embeddings_provider: Option<String>,
-    pub heartbeat_enabled: bool,
-    pub heartbeat_interval_secs: u64,
-    pub sandbox_enabled: bool,
-    pub claude_code_enabled: bool,
-    pub routines_enabled: bool,
-    pub channels: Vec<String>,
-}
-
-/// Print the boot screen to stdout.
-pub fn print_boot_screen(info: &BootInfo) {
-    // ANSI codes matching existing REPL palette
-    let bold = "\x1b[1m";
-    let cyan = "\x1b[36m";
-    let dim = "\x1b[90m";
-    let yellow_underline = "\x1b[33;4m";
-    let reset = "\x1b[0m";
-
-    let border = format!("  {dim}{}{reset}", "\u{2576}".repeat(58));
-
-    println!();
-    println!("{border}");
-    println!();
-    println!("  {bold}{}{reset} v{}", info.agent_name, info.version);
-    println!();
-
-    // Model line
-    let model_display = if let Some(ref cheap) = info.cheap_model {
-        format!(
-            "{cyan}{}{reset}  {dim}cheap{reset} {cyan}{}{reset}",
-            info.llm_model, cheap
-        )
-    } else {
-        format!("{cyan}{}{reset}", info.llm_model)
-    };
-    println!(
-        "  {dim}model{reset}     {model_display}  {dim}via {}{reset}",
-        info.llm_backend
-    );
-
-    // Database line
-    let db_status = if info.db_connected {
-        "connected"
-    } else {
-        "none"
-    };
-    println!(
-        "  {dim}database{reset}  {cyan}{}{reset} {dim}({db_status}){reset}",
-        info.db_backend
-    );
-
-    // Tools line
-    println!(
-        "  {dim}tools{reset}     {cyan}{}{reset} {dim}registered{reset}",
-        info.tool_count
-    );
-
-    // Features line
-    let mut features = Vec::new();
-    if info.embeddings_enabled {
-        if let Some(ref provider) = info.embeddings_provider {
-            features.push(format!("embeddings ({provider})"));
-        } else {
-            features.push("embeddings".to_string());
-        }
-    }
-    if info.heartbeat_enabled {
-        let mins = info.heartbeat_interval_secs / 60;
-        features.push(format!("heartbeat ({mins}m)"));
-    }
-    if info.sandbox_enabled {
-        features.push("sandbox".to_string());
-    }
-    if info.claude_code_enabled {
-        features.push("claude-code".to_string());
-    }
-    if info.routines_enabled {
-        features.push("routines".to_string());
-    }
-    if !features.is_empty() {
-        println!(
-            "  {dim}features{reset}  {cyan}{}{reset}",
-            features.join("  ")
-        );
-    }
-
-    // Channels line
-    if !info.channels.is_empty() {
-        println!(
-            "  {dim}channels{reset}  {cyan}{}{reset}",
-            info.channels.join("  ")
-        );
-    }
-
-    // Gateway URL (highlighted)
-    if let Some(ref url) = info.gateway_url {
-        println!();
-        println!("  {dim}gateway{reset}   {yellow_underline}{url}{reset}");
-    }
-
-    println!();
-    println!("{border}");
-    println!();
-    println!("  /help for commands, /quit to exit");
-    println!();
-}
-
-#[cfg(test)]
-mod tests {
-    use super::*;
-
-    #[test]
-    fn test_print_boot_screen_full() {
-        let info = BootInfo {
-            version: "0.2.0".to_string(),
-            agent_name: "ironclaw".to_string(),
-            llm_backend: "nearai".to_string(),
-            llm_model: "claude-3-5-sonnet-20241022".to_string(),
-            cheap_model: Some("gpt-4o-mini".to_string()),
-            db_backend: "libsql".to_string(),
-            db_connected: true,
-            tool_count: 24,
-            gateway_url: Some("http://127.0.0.1:3001/?token=abc123".to_string()),
-            embeddings_enabled: true,
-            embeddings_provider: Some("openai".to_string()),
-            heartbeat_enabled: true,
-            heartbeat_interval_secs: 1800,
-            sandbox_enabled: true,
-            claude_code_enabled: false,
-            routines_enabled: true,
-            channels: vec![
-                "repl".to_string(),
-                "gateway".to_string(),
-                "telegram".to_string(),
-            ],
-        };
-        // Should not panic
-        print_boot_screen(&info);
-    }
-
-    #[test]
-    fn test_print_boot_screen_minimal() {
-        let info = BootInfo {
-            version: "0.2.0".to_string(),
-            agent_name: "ironclaw".to_string(),
-            llm_backend: "nearai".to_string(),
-            llm_model: "gpt-4o".to_string(),
-            cheap_model: None,
-            db_backend: "none".to_string(),
-            db_connected: false,
-            tool_count: 5,
-            gateway_url: None,
-            embeddings_enabled: false,
-            embeddings_provider: None,
-            heartbeat_enabled: false,
-            heartbeat_interval_secs: 0,
-            sandbox_enabled: false,
-            claude_code_enabled: false,
-            routines_enabled: false,
-            channels: vec![],
-        };
-        // Should not panic
-        print_boot_screen(&info);
-    }
-
-    #[test]
-    fn test_print_boot_screen_no_features() {
-        let info = BootInfo {
-            version: "0.1.0".to_string(),
-            agent_name: "test".to_string(),
-            llm_backend: "openai".to_string(),
-            llm_model: "gpt-4o".to_string(),
-            cheap_model: None,
-            db_backend: "postgres".to_string(),
-            db_connected: true,
-            tool_count: 10,
-            gateway_url: None,
-            embeddings_enabled: false,
-            embeddings_provider: None,
-            heartbeat_enabled: false,
-            heartbeat_interval_secs: 0,
-            sandbox_enabled: false,
-            claude_code_enabled: false,
-            routines_enabled: false,
-            channels: vec!["repl".to_string()],
-        };
-        // Should not panic
-        print_boot_screen(&info);
-    }
-}

src/bootstrap.rs

@@ -1,145 +1,147 @@
-//! Bootstrap helpers for IronClaw.
+//! Bootstrap configuration for IronClaw.
 //!
-//! The only setting that truly needs disk persistence before the database is
-//! available is `DATABASE_URL` (chicken-and-egg: can't connect to DB without
-//! it). Everything else is auto-detected or read from env vars.
+//! These are the only settings that MUST live on disk because they're needed
+//! before the database connection is established. Everything else lives in the
+//! `settings` table in PostgreSQL.
 //!
-//! File: `~/.ironclaw/.env` (standard dotenvy format)
+//! File: `~/.ironclaw/bootstrap.json`
 
 use std::path::PathBuf;
 
-/// Path to the IronClaw-specific `.env` file: `~/.ironclaw/.env`.
-pub fn ironclaw_env_path() -> PathBuf {
-    dirs::home_dir()
-        .unwrap_or_else(|| PathBuf::from("."))
-        .join(".ironclaw")
-        .join(".env")
+use serde::{Deserialize, Serialize};
+
+use crate::settings::KeySource;
+
+/// Minimal config needed to connect to the database and decrypt secrets.
+///
+/// This is the only JSON file IronClaw reads from disk at startup.
+/// All other configuration lives in the `settings` table in PostgreSQL.
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct BootstrapConfig {
+    /// Database connection URL (postgres://...).
+    #[serde(default)]
+    pub database_url: Option<String>,
+
+    /// Database connection pool size.
+    #[serde(default)]
+    pub database_pool_size: Option<usize>,
+
+    /// Source for the secrets master key.
+    #[serde(default)]
+    pub secrets_master_key_source: KeySource,
+
+    /// Whether onboarding wizard has been completed.
+    #[serde(default)]
+    pub onboard_completed: bool,
 }
 
-/// Load env vars from `~/.ironclaw/.env` (in addition to the standard `.env`).
-///
-/// Call this **after** `dotenvy::dotenv()` so that the standard `./.env`
-/// takes priority over `~/.ironclaw/.env`. dotenvy never overwrites
-/// existing env vars, so the effective priority is:
-///
-///   explicit env vars > `./.env` > `~/.ironclaw/.env`
-///
-/// If `~/.ironclaw/.env` doesn't exist but the legacy `bootstrap.json` does,
-/// extracts `DATABASE_URL` from it and writes the `.env` file (one-time
-/// upgrade from the old config format).
-pub fn load_ironclaw_env() {
-    let path = ironclaw_env_path();
-
-    if !path.exists() {
-        // One-time upgrade: extract DATABASE_URL from legacy bootstrap.json
-        migrate_bootstrap_json_to_env(&path);
-    }
-
-    if path.exists() {
-        let _ = dotenvy::from_path(&path);
-    }
-}
-
-/// If `bootstrap.json` exists, pull `database_url` out of it and write `.env`.
-fn migrate_bootstrap_json_to_env(env_path: &std::path::Path) {
-    let ironclaw_dir = env_path
-        .parent()
-        .unwrap_or_else(|| std::path::Path::new("."));
-    let bootstrap_path = ironclaw_dir.join("bootstrap.json");
-
-    if !bootstrap_path.exists() {
-        return;
-    }
-
-    let content = match std::fs::read_to_string(&bootstrap_path) {
-        Ok(c) => c,
-        Err(_) => return,
-    };
-
-    // Minimal parse: just grab database_url from the JSON
-    let parsed: serde_json::Value = match serde_json::from_str(&content) {
-        Ok(v) => v,
-        Err(_) => return,
-    };
-
-    if let Some(url) = parsed.get("database_url").and_then(|v| v.as_str()) {
-        if let Some(parent) = env_path.parent()
-            && let Err(e) = std::fs::create_dir_all(parent)
-        {
-            eprintln!("Warning: failed to create {}: {}", parent.display(), e);
-            return;
+impl Default for BootstrapConfig {
+    fn default() -> Self {
+        Self {
+            database_url: None,
+            database_pool_size: None,
+            secrets_master_key_source: KeySource::None,
+            onboard_completed: false,
         }
-        if let Err(e) = std::fs::write(env_path, format!("DATABASE_URL=\"{}\"\n", url)) {
-            eprintln!("Warning: failed to migrate bootstrap.json to .env: {}", e);
-            return;
+    }
+}
+
+impl BootstrapConfig {
+    /// Default bootstrap file path: `~/.ironclaw/bootstrap.json`.
+    pub fn default_path() -> PathBuf {
+        dirs::home_dir()
+            .unwrap_or_else(|| PathBuf::from("."))
+            .join(".ironclaw")
+            .join("bootstrap.json")
+    }
+
+    /// Legacy settings.json path (for migration detection).
+    pub fn legacy_settings_path() -> PathBuf {
+        dirs::home_dir()
+            .unwrap_or_else(|| PathBuf::from("."))
+            .join(".ironclaw")
+            .join("settings.json")
+    }
+
+    /// Load from the default path, falling back to legacy settings.json,
+    /// then to defaults if neither exists.
+    pub fn load() -> Self {
+        let bootstrap_path = Self::default_path();
+        if bootstrap_path.exists() {
+            return Self::load_from(&bootstrap_path);
         }
-        rename_to_migrated(&bootstrap_path);
-        eprintln!(
-            "Migrated DATABASE_URL from bootstrap.json to {}",
-            env_path.display()
-        );
+
+        // Fall back to legacy settings.json (extract just the 4 bootstrap fields)
+        let legacy_path = Self::legacy_settings_path();
+        if legacy_path.exists() {
+            return Self::load_from_legacy(&legacy_path);
+        }
+
+        Self::default()
+    }
+
+    /// Load from a specific path.
+    pub fn load_from(path: &PathBuf) -> Self {
+        match std::fs::read_to_string(path) {
+            Ok(data) => serde_json::from_str(&data).unwrap_or_default(),
+            Err(_) => Self::default(),
+        }
+    }
+
+    /// Extract bootstrap fields from a legacy settings.json.
+    fn load_from_legacy(path: &PathBuf) -> Self {
+        match std::fs::read_to_string(path) {
+            Ok(data) => {
+                // The legacy Settings struct is a superset; serde will ignore extra fields.
+                serde_json::from_str(&data).unwrap_or_default()
+            }
+            Err(_) => Self::default(),
+        }
+    }
+
+    /// Save to the default path.
+    pub fn save(&self) -> std::io::Result<()> {
+        self.save_to(&Self::default_path())
+    }
+
+    /// Save to a specific path.
+    pub fn save_to(&self, path: &PathBuf) -> std::io::Result<()> {
+        if let Some(parent) = path.parent() {
+            std::fs::create_dir_all(parent)?;
+        }
+        let json = serde_json::to_string_pretty(self)
+            .map_err(|e| std::io::Error::new(std::io::ErrorKind::InvalidData, e.to_string()))?;
+        std::fs::write(path, json)
     }
 }
 
-/// Write database bootstrap vars to `~/.ironclaw/.env`.
+/// One-time migration from disk config files to the database settings table.
 ///
-/// These settings form the chicken-and-egg layer: they must be available
-/// from the filesystem (env vars) BEFORE any database connection, because
-/// they determine which database to connect to. Everything else is stored
-/// in the database itself.
+/// On first boot after upgrade, checks if:
+/// 1. `~/.ironclaw/settings.json` exists
+/// 2. The DB settings table is empty for this user
 ///
-/// Creates the parent directory if it doesn't exist.
-/// Values are double-quoted so that `#` (common in URL-encoded passwords)
-/// and other shell-special characters are preserved by dotenvy.
-pub fn save_bootstrap_env(vars: &[(&str, &str)]) -> std::io::Result<()> {
-    let path = ironclaw_env_path();
-    if let Some(parent) = path.parent() {
-        std::fs::create_dir_all(parent)?;
-    }
-    let mut content = String::new();
-    for (key, value) in vars {
-        content.push_str(&format!("{}=\"{}\"\n", key, value));
-    }
-    std::fs::write(&path, content)
-}
-
-/// Write `DATABASE_URL` to `~/.ironclaw/.env`.
-///
-/// Convenience wrapper around `save_bootstrap_env` for single-value migration
-/// paths. Prefer `save_bootstrap_env` for new code.
-pub fn save_database_url(url: &str) -> std::io::Result<()> {
-    save_bootstrap_env(&[("DATABASE_URL", url)])
-}
-
-/// One-time migration of legacy `~/.ironclaw/settings.json` into the database.
-///
-/// Only runs when a `settings.json` exists on disk AND the DB has no settings
-/// yet. After the wizard writes directly to the DB, this path is only hit by
-/// users upgrading from the old disk-only configuration.
-///
-/// After syncing, renames `settings.json` to `.migrated` so it won't trigger again.
+/// If both conditions hold, migrates settings, MCP servers, and session data
+/// to the database, writes `bootstrap.json`, and renames old files to `.migrated`.
 pub async fn migrate_disk_to_db(
     store: &dyn crate::db::Database,
     user_id: &str,
 ) -> Result<(), MigrationError> {
-    let ironclaw_dir = dirs::home_dir()
-        .unwrap_or_else(|| PathBuf::from("."))
-        .join(".ironclaw");
-    let legacy_settings_path = ironclaw_dir.join("settings.json");
-
+    let legacy_settings_path = BootstrapConfig::legacy_settings_path();
     if !legacy_settings_path.exists() {
         tracing::debug!("No legacy settings.json found, skipping disk-to-DB migration");
         return Ok(());
     }
 
-    // If DB already has settings, this is not a first boot, the wizard already
-    // wrote directly to the DB. Just clean up the stale file.
+    // Only migrate if DB is empty for this user
     let has_settings = store.has_settings(user_id).await.map_err(|e| {
         MigrationError::Database(format!("Failed to check existing settings: {}", e))
     })?;
     if has_settings {
-        tracing::info!("DB already has settings, renaming stale settings.json");
-        rename_to_migrated(&legacy_settings_path);
+        tracing::debug!(
+            "DB already has settings for user '{}', skipping migration",
+            user_id
+        );
         return Ok(());
     }
 
@@ -158,14 +160,22 @@ pub async fn migrate_disk_to_db(
         tracing::info!("Migrated {} settings to database", db_map.len());
     }
 
-    // 2. Write DATABASE_URL to ~/.ironclaw/.env
-    if let Some(ref url) = settings.database_url {
-        save_database_url(url)
-            .map_err(|e| MigrationError::Io(format!("Failed to write .env: {}", e)))?;
-        tracing::info!("Wrote DATABASE_URL to {}", ironclaw_env_path().display());
-    }
+    // 2. Write bootstrap.json with the 4 essential fields
+    let bootstrap = BootstrapConfig {
+        database_url: settings.database_url.clone(),
+        database_pool_size: settings.database_pool_size,
+        secrets_master_key_source: settings.secrets_master_key_source,
+        onboard_completed: settings.onboard_completed,
+    };
+    bootstrap
+        .save()
+        .map_err(|e| MigrationError::Io(format!("Failed to write bootstrap.json: {}", e)))?;
+    tracing::info!("Wrote bootstrap.json");
 
     // 3. Migrate mcp-servers.json if it exists
+    let ironclaw_dir = dirs::home_dir()
+        .unwrap_or_else(|| PathBuf::from("."))
+        .join(".ironclaw");
     let mcp_path = ironclaw_dir.join("mcp-servers.json");
     if mcp_path.exists() {
         match std::fs::read_to_string(&mcp_path) {
@@ -201,7 +211,7 @@ pub async fn migrate_disk_to_db(
             Ok(content) => match serde_json::from_str::<serde_json::Value>(&content) {
                 Ok(value) => {
                     store
-                        .set_setting(user_id, "nearai.session_token", &value)
+                        .set_setting(user_id, "nearai.session", &value)
                         .await
                         .map_err(|e| {
                             MigrationError::Database(format!(
@@ -226,19 +236,12 @@ pub async fn migrate_disk_to_db(
     // 5. Rename settings.json to .migrated (don't delete, safety net)
     rename_to_migrated(&legacy_settings_path);
 
-    // 6. Clean up old bootstrap.json if it exists (superseded by .env)
-    let old_bootstrap = ironclaw_dir.join("bootstrap.json");
-    if old_bootstrap.exists() {
-        rename_to_migrated(&old_bootstrap);
-        tracing::info!("Renamed old bootstrap.json to .migrated");
-    }
-
     tracing::info!("Disk-to-DB migration complete");
     Ok(())
 }
 
 /// Rename a file to `<name>.migrated` as a safety net.
-fn rename_to_migrated(path: &std::path::Path) {
+fn rename_to_migrated(path: &PathBuf) {
     let mut migrated = path.as_os_str().to_owned();
     migrated.push(".migrated");
     if let Err(e) = std::fs::rename(path, &migrated) {
@@ -261,204 +264,62 @@ mod tests {
     use tempfile::tempdir;
 
     #[test]
-    fn test_save_and_load_database_url() {
+    fn test_bootstrap_save_load() {
         let dir = tempdir().unwrap();
-        let env_path = dir.path().join(".env");
+        let path = dir.path().join("bootstrap.json");
 
-        // Write in the quoted format that save_database_url uses
-        let url = "postgres://localhost:5432/ironclaw_test";
-        std::fs::write(&env_path, format!("DATABASE_URL=\"{}\"\n", url)).unwrap();
+        let config = BootstrapConfig {
+            database_url: Some("postgres://localhost/test".to_string()),
+            database_pool_size: Some(5),
+            secrets_master_key_source: KeySource::Keychain,
+            onboard_completed: true,
+        };
 
-        // Verify the content is a valid dotenv line (quoted)
-        let content = std::fs::read_to_string(&env_path).unwrap();
+        config.save_to(&path).unwrap();
+
+        let loaded = BootstrapConfig::load_from(&path);
         assert_eq!(
-            content,
-            "DATABASE_URL=\"postgres://localhost:5432/ironclaw_test\"\n"
+            loaded.database_url,
+            Some("postgres://localhost/test".to_string())
         );
-
-        // Verify dotenvy can parse it (strips quotes automatically)
-        let parsed: Vec<(String, String)> = dotenvy::from_path_iter(&env_path)
-            .unwrap()
-            .filter_map(|r| r.ok())
-            .collect();
-        assert_eq!(parsed.len(), 1);
-        assert_eq!(parsed[0].0, "DATABASE_URL");
-        assert_eq!(parsed[0].1, url);
+        assert_eq!(loaded.database_pool_size, Some(5));
+        assert_eq!(loaded.secrets_master_key_source, KeySource::Keychain);
+        assert!(loaded.onboard_completed);
     }
 
     #[test]
-    fn test_save_database_url_with_hash_in_password() {
+    fn test_bootstrap_from_legacy_settings() {
         let dir = tempdir().unwrap();
-        let env_path = dir.path().join(".env");
+        let path = dir.path().join("settings.json");
 
-        // URLs with # in the password are common (URL-encoded special chars).
-        // Without quoting, dotenvy treats # as a comment delimiter.
-        let url = "postgres://user:p%23ss@localhost:5432/ironclaw";
-        std::fs::write(&env_path, format!("DATABASE_URL=\"{}\"\n", url)).unwrap();
-
-        let parsed: Vec<(String, String)> = dotenvy::from_path_iter(&env_path)
-            .unwrap()
-            .filter_map(|r| r.ok())
-            .collect();
-        assert_eq!(parsed.len(), 1);
-        assert_eq!(parsed[0].0, "DATABASE_URL");
-        assert_eq!(parsed[0].1, url);
-    }
-
-    #[test]
-    fn test_save_database_url_creates_parent_dirs() {
-        let dir = tempdir().unwrap();
-        let nested = dir.path().join("deep").join("nested");
-        let env_path = nested.join(".env");
-
-        // Parent doesn't exist yet
-        assert!(!nested.exists());
-
-        // The global function uses a fixed path, so we test the logic directly
-        std::fs::create_dir_all(&nested).unwrap();
-        std::fs::write(&env_path, "DATABASE_URL=postgres://test\n").unwrap();
-
-        assert!(env_path.exists());
-        let content = std::fs::read_to_string(&env_path).unwrap();
-        assert!(content.contains("DATABASE_URL=postgres://test"));
-    }
-
-    #[test]
-    fn test_ironclaw_env_path() {
-        let path = ironclaw_env_path();
-        assert!(path.ends_with(".ironclaw/.env"));
-    }
-
-    #[test]
-    fn test_migrate_bootstrap_json_to_env() {
-        let dir = tempdir().unwrap();
-        let env_path = dir.path().join(".env");
-        let bootstrap_path = dir.path().join("bootstrap.json");
-
-        // Write a legacy bootstrap.json
-        let bootstrap_json = serde_json::json!({
-            "database_url": "postgres://localhost/ironclaw_upgrade",
-            "database_pool_size": 5,
+        // Write a legacy settings.json with many extra fields
+        let legacy = serde_json::json!({
+            "database_url": "postgres://localhost/ironclaw",
+            "database_pool_size": 10,
             "secrets_master_key_source": "keychain",
-            "onboard_completed": true
+            "onboard_completed": true,
+            "selected_model": "claude-3-5-sonnet",
+            "agent": { "name": "testbot", "max_parallel_jobs": 3 },
+            "heartbeat": { "enabled": true }
         });
-        std::fs::write(
-            &bootstrap_path,
-            serde_json::to_string_pretty(&bootstrap_json).unwrap(),
-        )
-        .unwrap();
+        std::fs::write(&path, serde_json::to_string_pretty(&legacy).unwrap()).unwrap();
 
-        assert!(!env_path.exists());
-        assert!(bootstrap_path.exists());
-
-        // Run the migration
-        migrate_bootstrap_json_to_env(&env_path);
-
-        // .env should now exist with DATABASE_URL
-        assert!(env_path.exists());
-        let content = std::fs::read_to_string(&env_path).unwrap();
+        let config = BootstrapConfig::load_from_legacy(&path);
         assert_eq!(
-            content,
-            "DATABASE_URL=\"postgres://localhost/ironclaw_upgrade\"\n"
+            config.database_url,
+            Some("postgres://localhost/ironclaw".to_string())
         );
-
-        // bootstrap.json should be renamed to .migrated
-        assert!(!bootstrap_path.exists());
-        assert!(dir.path().join("bootstrap.json.migrated").exists());
+        assert_eq!(config.database_pool_size, Some(10));
+        assert_eq!(config.secrets_master_key_source, KeySource::Keychain);
+        assert!(config.onboard_completed);
     }
 
     #[test]
-    fn test_migrate_bootstrap_json_no_database_url() {
-        let dir = tempdir().unwrap();
-        let env_path = dir.path().join(".env");
-        let bootstrap_path = dir.path().join("bootstrap.json");
-
-        // bootstrap.json with no database_url
-        let bootstrap_json = serde_json::json!({
-            "onboard_completed": false
-        });
-        std::fs::write(
-            &bootstrap_path,
-            serde_json::to_string_pretty(&bootstrap_json).unwrap(),
-        )
-        .unwrap();
-
-        migrate_bootstrap_json_to_env(&env_path);
-
-        // .env should NOT be created
-        assert!(!env_path.exists());
-        // bootstrap.json should remain (no migration happened)
-        assert!(bootstrap_path.exists());
-    }
-
-    #[test]
-    fn test_migrate_bootstrap_json_missing() {
-        let dir = tempdir().unwrap();
-        let env_path = dir.path().join(".env");
-
-        // No bootstrap.json at all
-        migrate_bootstrap_json_to_env(&env_path);
-
-        // Nothing should happen
-        assert!(!env_path.exists());
-    }
-
-    #[test]
-    fn test_save_bootstrap_env_multiple_vars() {
-        let dir = tempdir().unwrap();
-        let env_path = dir.path().join("nested").join(".env");
-
-        std::fs::create_dir_all(env_path.parent().unwrap()).unwrap();
-
-        let vars = [
-            ("DATABASE_BACKEND", "libsql"),
-            ("LIBSQL_PATH", "/home/user/.ironclaw/ironclaw.db"),
-        ];
-
-        // Write manually to the temp path (save_bootstrap_env uses the global path)
-        let mut content = String::new();
-        for (key, value) in &vars {
-            content.push_str(&format!("{}=\"{}\"\n", key, value));
-        }
-        std::fs::write(&env_path, &content).unwrap();
-
-        // Verify dotenvy can parse all entries
-        let parsed: Vec<(String, String)> = dotenvy::from_path_iter(&env_path)
-            .unwrap()
-            .filter_map(|r| r.ok())
-            .collect();
-        assert_eq!(parsed.len(), 2);
-        assert_eq!(
-            parsed[0],
-            ("DATABASE_BACKEND".to_string(), "libsql".to_string())
-        );
-        assert_eq!(
-            parsed[1],
-            (
-                "LIBSQL_PATH".to_string(),
-                "/home/user/.ironclaw/ironclaw.db".to_string()
-            )
-        );
-    }
-
-    #[test]
-    fn test_save_bootstrap_env_overwrites_previous() {
-        let dir = tempdir().unwrap();
-        let env_path = dir.path().join(".env");
-
-        // Write initial content
-        std::fs::write(&env_path, "DATABASE_URL=\"postgres://old\"\n").unwrap();
-
-        // Overwrite with new vars (simulating save_bootstrap_env behavior)
-        let content = "DATABASE_BACKEND=\"libsql\"\nLIBSQL_PATH=\"/new/path.db\"\n";
-        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();
-        // Old DATABASE_URL should be gone
-        assert_eq!(parsed.len(), 2);
-        assert!(parsed.iter().all(|(k, _)| k != "DATABASE_URL"));
+    fn test_bootstrap_defaults() {
+        let config = BootstrapConfig::default();
+        assert!(config.database_url.is_none());
+        assert!(config.database_pool_size.is_none());
+        assert_eq!(config.secrets_master_key_source, KeySource::None);
+        assert!(!config.onboard_completed);
     }
 }

src/channels/repl.rs

@@ -33,16 +33,9 @@ use termimad::MadSkin;
 use tokio::sync::mpsc;
 use tokio_stream::wrappers::ReceiverStream;
 
-use crate::agent::truncate_for_preview;
 use crate::channels::{Channel, IncomingMessage, MessageStream, OutgoingResponse, StatusUpdate};
 use crate::error::ChannelError;
 
-/// Max characters for tool result previews in the terminal.
-const CLI_TOOL_RESULT_MAX: usize = 200;
-
-/// Max characters for thinking/status messages in the terminal.
-const CLI_STATUS_MAX: usize = 200;
-
 /// Slash commands available in the REPL.
 const SLASH_COMMANDS: &[&str] = &[
     "/help",
@@ -184,8 +177,6 @@ pub struct ReplChannel {
     debug_mode: Arc<AtomicBool>,
     /// Whether we're currently streaming (chunks have been printed without a trailing newline).
     is_streaming: Arc<AtomicBool>,
-    /// When true, the one-liner startup banner is suppressed (boot screen shown instead).
-    suppress_banner: Arc<AtomicBool>,
 }
 
 impl ReplChannel {
@@ -195,7 +186,6 @@ impl ReplChannel {
             single_message: None,
             debug_mode: Arc::new(AtomicBool::new(false)),
             is_streaming: Arc::new(AtomicBool::new(false)),
-            suppress_banner: Arc::new(AtomicBool::new(false)),
         }
     }
 
@@ -205,15 +195,9 @@ impl ReplChannel {
             single_message: Some(message),
             debug_mode: Arc::new(AtomicBool::new(false)),
             is_streaming: Arc::new(AtomicBool::new(false)),
-            suppress_banner: Arc::new(AtomicBool::new(false)),
         }
     }
 
-    /// Suppress the one-liner startup banner (boot screen will be shown instead).
-    pub fn suppress_banner(&self) {
-        self.suppress_banner.store(true, Ordering::Relaxed);
-    }
-
     fn is_debug(&self) -> bool {
         self.debug_mode.load(Ordering::Relaxed)
     }
@@ -273,12 +257,11 @@ impl Channel for ReplChannel {
         let (tx, rx) = mpsc::channel(32);
         let single_message = self.single_message.clone();
         let debug_mode = Arc::clone(&self.debug_mode);
-        let suppress_banner = Arc::clone(&self.suppress_banner);
 
         std::thread::spawn(move || {
             // Single message mode: send it and return
             if let Some(msg) = single_message {
-                let incoming = IncomingMessage::new("repl", "default", &msg);
+                let incoming = IncomingMessage::new("repl", "user", &msg);
                 let _ = tx.blocking_send(incoming);
                 return;
             }
@@ -308,10 +291,8 @@ impl Channel for ReplChannel {
             }
             let _ = rl.load_history(&hist_path);
 
-            if !suppress_banner.load(Ordering::Relaxed) {
-                println!("\x1b[1mIronClaw\x1b[0m  /help for commands, /quit to exit");
-                println!();
-            }
+            println!("\x1b[1mIronClaw\x1b[0m  /help for commands, /quit to exit");
+            println!();
 
             loop {
                 let prompt = if debug_mode.load(Ordering::Relaxed) {
@@ -348,21 +329,21 @@ impl Channel for ReplChannel {
                             _ => {}
                         }
 
-                        let msg = IncomingMessage::new("repl", "default", line);
+                        let msg = IncomingMessage::new("repl", "user", line);
                         if tx.blocking_send(msg).is_err() {
                             break;
                         }
                     }
                     Err(ReadlineError::Interrupted) => {
                         // Ctrl+C: send /interrupt
-                        let msg = IncomingMessage::new("repl", "default", "/interrupt");
+                        let msg = IncomingMessage::new("repl", "user", "/interrupt");
                         if tx.blocking_send(msg).is_err() {
                             break;
                         }
                     }
                     Err(ReadlineError::Eof) => {
                         // Ctrl+D: send /quit so the agent loop runs graceful shutdown
-                        let msg = IncomingMessage::new("repl", "default", "/quit");
+                        let msg = IncomingMessage::new("repl", "user", "/quit");
                         let _ = tx.blocking_send(msg);
                         break;
                     }
@@ -419,8 +400,7 @@ impl Channel for ReplChannel {
 
         match status {
             StatusUpdate::Thinking(msg) => {
-                let display = truncate_for_preview(&msg, CLI_STATUS_MAX);
-                eprintln!("  \x1b[90m\u{25CB} {display}\x1b[0m");
+                eprintln!("  \x1b[90m\u{25CB} {msg}\x1b[0m");
             }
             StatusUpdate::ToolStarted { name } => {
                 eprintln!("  \x1b[33m\u{25CB} {name}\x1b[0m");
@@ -433,8 +413,7 @@ impl Channel for ReplChannel {
                 }
             }
             StatusUpdate::ToolResult { name: _, preview } => {
-                let display = truncate_for_preview(&preview, CLI_TOOL_RESULT_MAX);
-                eprintln!("    \x1b[90m{display}\x1b[0m");
+                eprintln!("    \x1b[90m{preview}\x1b[0m");
             }
             StatusUpdate::StreamChunk(chunk) => {
                 // Print separator on the false-to-true transition
@@ -459,8 +438,7 @@ impl Channel for ReplChannel {
             }
             StatusUpdate::Status(msg) => {
                 if debug || msg.contains("approval") || msg.contains("Approval") {
-                    let display = truncate_for_preview(&msg, CLI_STATUS_MAX);
-                    eprintln!("  \x1b[90m{display}\x1b[0m");
+                    eprintln!("  \x1b[90m{msg}\x1b[0m");
                 }
             }
             StatusUpdate::ApprovalNeeded {

src/channels/wasm/wrapper.rs

@@ -76,9 +76,6 @@ struct ChannelStoreData {
     credentials: HashMap<String, String>,
     /// Pairing store for DM pairing (guest access control).
     pairing_store: Arc<PairingStore>,
-    /// Dedicated tokio runtime for HTTP requests, lazily initialized.
-    /// Reused across multiple `http_request` calls within one execution.
-    http_runtime: Option<tokio::runtime::Runtime>,
 }
 
 impl ChannelStoreData {
@@ -99,7 +96,6 @@ impl ChannelStoreData {
             table: ResourceTable::new(),
             credentials,
             pairing_store,
-            http_runtime: None,
         }
     }
 
@@ -138,13 +134,13 @@ impl ChannelStoreData {
         if result.contains('{') && result.contains('}') {
             // Only warn if it looks like an unresolved placeholder (not JSON braces)
             let brace_pattern = regex::Regex::new(r"\{[A-Z_]+\}").ok();
-            if let Some(re) = brace_pattern
-                && re.is_match(&result)
-            {
-                tracing::warn!(
-                    context = %context,
-                    "String may contain unresolved credential placeholders"
-                );
+            if let Some(re) = brace_pattern {
+                if re.is_match(&result) {
+                    tracing::warn!(
+                        context = %context,
+                        "String may contain unresolved credential placeholders"
+                    );
+                }
             }
         }
 
@@ -287,25 +283,10 @@ impl near::agent::channel_host::Host for ChannelStoreData {
             .map(|h| h.max_response_bytes)
             .unwrap_or(10 * 1024 * 1024);
 
-        // Make the HTTP request using a dedicated single-threaded runtime.
-        // We're inside spawn_blocking, so we can't rely on the main runtime's
-        // I/O driver (it may be busy with WASM compilation or other startup work).
-        // A dedicated runtime gives us our own I/O driver and avoids contention.
-        // The runtime is lazily created and reused across calls within one execution.
-        if self.http_runtime.is_none() {
-            self.http_runtime = Some(
-                tokio::runtime::Builder::new_current_thread()
-                    .enable_all()
-                    .build()
-                    .map_err(|e| format!("Failed to create HTTP runtime: {e}"))?,
-            );
-        }
-        let rt = self.http_runtime.as_ref().expect("just initialized");
-        let result = rt.block_on(async {
-            let client = reqwest::Client::builder()
-                .connect_timeout(std::time::Duration::from_secs(10))
-                .build()
-                .map_err(|e| format!("Failed to build HTTP client: {e}"))?;
+        // Make the HTTP request using blocking I/O
+        // We're already in a spawn_blocking context, so we can use block_on
+        let result = tokio::runtime::Handle::current().block_on(async {
+            let client = reqwest::Client::new();
 
             let mut request = match method.to_uppercase().as_str() {
                 "GET" => client.get(&url),
@@ -327,9 +308,9 @@ impl near::agent::channel_host::Host for ChannelStoreData {
                 request = request.body(body_bytes);
             }
 
-            // Send request with caller-specified timeout (default 30s, max 5min).
-            let timeout_ms = timeout_ms.unwrap_or(30_000).min(300_000) as u64;
-            let timeout = std::time::Duration::from_millis(timeout_ms);
+            // Send request with caller-specified timeout (default 30s).
+            // Cap at callback_timeout to prevent outliving the host wrapper.
+            let timeout = std::time::Duration::from_millis(timeout_ms.unwrap_or(30_000) as u64);
             let response = request.timeout(timeout).send().await.map_err(|e| {
                 // Walk the full error chain so we get the actual root cause
                 // (DNS, TLS, connection refused, etc.) instead of just
@@ -357,13 +338,13 @@ impl near::agent::channel_host::Host for ChannelStoreData {
 
             // Enforce max response body size to prevent memory exhaustion.
             let max_response = max_response_bytes;
-            if let Some(cl) = response.content_length()
-                && cl as usize > max_response
-            {
-                return Err(format!(
-                    "Response body too large: {} bytes exceeds limit of {} bytes",
-                    cl, max_response
-                ));
+            if let Some(cl) = response.content_length() {
+                if cl as usize > max_response {
+                    return Err(format!(
+                        "Response body too large: {} bytes exceeds limit of {} bytes",
+                        cl, max_response
+                    ));
+                }
             }
             let body = response
                 .bytes()
@@ -814,21 +795,7 @@ impl WasmChannel {
         .await;
 
         match result {
-            Ok(Ok((config, mut host_state))) => {
-                // Surface WASM guest logs (errors/warnings from webhook setup, etc.)
-                for entry in host_state.take_logs() {
-                    match entry.level {
-                        crate::tools::wasm::LogLevel::Error => {
-                            tracing::error!(channel = %self.name, "{}", entry.message);
-                        }
-                        crate::tools::wasm::LogLevel::Warn => {
-                            tracing::warn!(channel = %self.name, "{}", entry.message);
-                        }
-                        _ => {
-                            tracing::debug!(channel = %self.name, "{}", entry.message);
-                        }
-                    }
-                }
+            Ok(Ok((config, _host_state))) => {
                 tracing::info!(
                     channel = %self.name,
                     display_name = %config.display_name,
@@ -1528,8 +1495,8 @@ impl WasmChannel {
                         match result {
                             Ok(emitted_messages) => {
                                 // Process any emitted messages
-                                if !emitted_messages.is_empty()
-                                    && let Err(e) = Self::dispatch_emitted_messages(
+                                if !emitted_messages.is_empty() {
+                                    if let Err(e) = Self::dispatch_emitted_messages(
                                         &channel_name,
                                         emitted_messages,
                                         &message_tx,
@@ -1541,6 +1508,7 @@ impl WasmChannel {
                                             "Failed to dispatch emitted messages from poll"
                                         );
                                     }
+                                }
                             }
                             Err(e) => {
                                 tracing::warn!(
@@ -1770,22 +1738,22 @@ impl Channel for WasmChannel {
         *self.endpoints.write().await = endpoints;
 
         // Start polling if configured
-        if let Some(poll_config) = &config.poll
-            && poll_config.enabled
-        {
-            let interval = self
-                .capabilities
-                .validate_poll_interval(poll_config.interval_ms)
-                .map_err(|e| ChannelError::StartupFailed {
-                    name: self.name.clone(),
-                    reason: e,
-                })?;
+        if let Some(poll_config) = &config.poll {
+            if poll_config.enabled {
+                let interval = self
+                    .capabilities
+                    .validate_poll_interval(poll_config.interval_ms)
+                    .map_err(|e| ChannelError::StartupFailed {
+                        name: self.name.clone(),
+                        reason: e,
+                    })?;
 
-            // Create shutdown channel for polling and store the sender to keep it alive
-            let (poll_shutdown_tx, poll_shutdown_rx) = oneshot::channel();
-            *self.poll_shutdown_tx.write().await = Some(poll_shutdown_tx);
+                // Create shutdown channel for polling and store the sender to keep it alive
+                let (poll_shutdown_tx, poll_shutdown_rx) = oneshot::channel();
+                *self.poll_shutdown_tx.write().await = Some(poll_shutdown_tx);
 
-            self.start_polling(Duration::from_millis(interval as u64), poll_shutdown_rx);
+                self.start_polling(Duration::from_millis(interval as u64), poll_shutdown_rx);
+            }
         }
 
         tracing::info!(
@@ -2648,52 +2616,15 @@ mod tests {
         assert_eq!(store.redact_credentials(input), input);
     }
 
-    /// Verify that WASM HTTP host functions work using a dedicated
-    /// current-thread runtime inside spawn_blocking.
+    /// Verify that the block_on-inside-spawn_blocking pattern used by the WASM
+    /// channel HTTP host function doesn't deadlock or panic.
     #[tokio::test]
-    async fn test_dedicated_runtime_inside_spawn_blocking() {
+    async fn test_block_on_inside_spawn_blocking_does_not_deadlock() {
         let result = tokio::task::spawn_blocking(|| {
-            let rt = tokio::runtime::Builder::new_current_thread()
-                .enable_all()
-                .build()
-                .expect("failed to build runtime");
-            rt.block_on(async { 42 })
+            tokio::runtime::Handle::current().block_on(async { 42 })
         })
         .await
         .expect("spawn_blocking panicked");
         assert_eq!(result, 42);
     }
-
-    /// Verify a real HTTP request works using the dedicated-runtime pattern.
-    /// This catches DNS, TLS, and I/O driver issues that trivial tests miss.
-    #[tokio::test]
-    #[ignore] // requires network
-    async fn test_dedicated_runtime_real_http() {
-        let result = tokio::task::spawn_blocking(|| {
-            let rt = tokio::runtime::Builder::new_current_thread()
-                .enable_all()
-                .build()
-                .expect("failed to build runtime");
-            rt.block_on(async {
-                let client = reqwest::Client::builder()
-                    .connect_timeout(std::time::Duration::from_secs(10))
-                    .build()
-                    .expect("failed to build client");
-                let resp = client
-                    .get("https://api.telegram.org/bot000/getMe")
-                    .timeout(std::time::Duration::from_secs(10))
-                    .send()
-                    .await;
-                match resp {
-                    Ok(r) => r.status().as_u16(),
-                    Err(e) if e.is_timeout() => panic!("request timed out: {e}"),
-                    Err(e) => panic!("unexpected error: {e}"),
-                }
-            })
-        })
-        .await
-        .expect("spawn_blocking panicked");
-        // 404 because "000" is not a valid bot token
-        assert_eq!(result, 404);
-    }
 }

src/channels/web/auth.rs

@@ -25,21 +25,23 @@ pub async fn auth_middleware(
     next: Next,
 ) -> Response {
     // Try Authorization header first (constant-time comparison)
-    if let Some(auth_header) = headers.get("authorization")
-        && let Ok(value) = auth_header.to_str()
-        && let Some(token) = value.strip_prefix("Bearer ")
-        && bool::from(token.as_bytes().ct_eq(auth.token.as_bytes()))
-    {
-        return next.run(request).await;
+    if let Some(auth_header) = headers.get("authorization") {
+        if let Ok(value) = auth_header.to_str() {
+            if let Some(token) = value.strip_prefix("Bearer ") {
+                if bool::from(token.as_bytes().ct_eq(auth.token.as_bytes())) {
+                    return next.run(request).await;
+                }
+            }
+        }
     }
 
     // Fall back to query parameter for SSE EventSource (constant-time comparison)
     if let Some(query) = request.uri().query() {
         for pair in query.split('&') {
-            if let Some(token) = pair.strip_prefix("token=")
-                && bool::from(token.as_bytes().ct_eq(auth.token.as_bytes()))
-            {
-                return next.run(request).await;
+            if let Some(token) = pair.strip_prefix("token=") {
+                if bool::from(token.as_bytes().ct_eq(auth.token.as_bytes())) {
+                    return next.run(request).await;
+                }
             }
         }
     }

src/channels/web/openai_compat.rs

@@ -473,10 +473,10 @@ pub async fn chat_completions_handler(
         if let Some(mt) = req.max_tokens {
             tool_req = tool_req.with_max_tokens(mt);
         }
-        if let Some(ref tc) = req.tool_choice
-            && let Some(choice) = normalize_tool_choice(tc)
-        {
-            tool_req = tool_req.with_tool_choice(choice);
+        if let Some(ref tc) = req.tool_choice {
+            if let Some(choice) = normalize_tool_choice(tc) {
+                tool_req = tool_req.with_tool_choice(choice);
+            }
         }
 
         let resp = llm
@@ -591,10 +591,10 @@ async fn handle_streaming(
         if let Some(mt) = req.max_tokens {
             tool_req = tool_req.with_max_tokens(mt);
         }
-        if let Some(ref tc) = req.tool_choice
-            && let Some(choice) = normalize_tool_choice(tc)
-        {
-            tool_req = tool_req.with_tool_choice(choice);
+        if let Some(ref tc) = req.tool_choice {
+            if let Some(choice) = normalize_tool_choice(tc) {
+                tool_req = tool_req.with_tool_choice(choice);
+            }
         }
         LlmResult::WithTools(
             llm.complete_with_tools(tool_req)

src/channels/web/server.rs

@@ -525,10 +525,10 @@ 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;
+        if let Some(thread_id) = sess.active_thread {
+            if let Some(thread) = sess.threads.get_mut(&thread_id) {
+                thread.pending_auth = None;
+            }
         }
     }
 }
@@ -626,69 +626,69 @@ async fn chat_history_handler(
     // Verify the thread belongs to the authenticated user before returning any data.
     // In-memory threads are already scoped by user via session_manager, but DB
     // lookups could expose another user's conversation if the UUID is guessed.
-    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()));
+    if query.thread_id.is_some() {
+        if 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()))?;
+    if before_cursor.is_some() {
+        if 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,
-        }));
+            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();
+    if let Some(thread) = sess.threads.get(&thread_id) {
+        if !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,
-        }));
+            return Ok(Json(HistoryResponse {
+                thread_id,
+                turns,
+                has_more: false,
+                oldest_timestamp: None,
+            }));
+        }
     }
 
     // Fall back to DB for historical threads not in memory (paginated)
@@ -738,12 +738,12 @@ fn build_turns_from_db_messages(messages: &[crate::history::ConversationMessage]
             };
 
             // 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());
+            if let Some(next) = iter.peek() {
+                if 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)
@@ -1126,65 +1126,65 @@ async fn jobs_detail_handler(
         .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());
+    if let Some(ref store) = state.store {
+        if 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 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,
+            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
             });
-        }
-        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,
-        }));
+            // 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()))
@@ -1198,35 +1198,35 @@ async fn jobs_cancel_handler(
         .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");
+    if let Some(ref store) = state.store {
+        if 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()));
             }
-            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()))?;
+            if job.status == "running" || job.status == "creating" {
+                // Stop the container if we have a job manager.
+                if let Some(ref jm) = state.job_manager {
+                    if 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,
+            })));
         }
-        return Ok(Json(serde_json::json!({
-            "status": "cancelled",
-            "job_id": job_id,
-        })));
     }
 
     Err((StatusCode::NOT_FOUND, "Job not found".to_string()))
@@ -1334,13 +1334,14 @@ async fn jobs_prompt_handler(
         .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid job ID".to_string()))?;
 
     // Verify user owns this job.
-    if let Some(ref store) = state.store
-        && !store
+    if let Some(ref store) = state.store {
+        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()));
+        {
+            return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
+        }
     }
 
     let content = body

src/channels/web/static/app.js

@@ -12,7 +12,6 @@ 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 ---
 
@@ -1002,12 +1001,9 @@ function buildBreadcrumb(path) {
 }
 
 function searchMemory(query) {
-  const normalizedQuery = normalizeSearchQuery(query);
-  if (!normalizedQuery) return;
-
   apiFetch('/api/memory/search', {
     method: 'POST',
-    body: { query: normalizedQuery, limit: 20 },
+    body: { query, limit: 20 },
   }).then((data) => {
     const tree = document.getElementById('memory-tree');
     tree.innerHTML = '';
@@ -1018,23 +1014,18 @@ function searchMemory(query) {
     for (const result of data.results) {
       const item = document.createElement('div');
       item.className = 'search-result';
-      const snippet = snippetAround(result.content, normalizedQuery, 120);
+      const snippet = snippetAround(result.content, query, 120);
       item.innerHTML = '<div class="path">' + escapeHtml(result.path) + '</div>'
-        + '<div class="snippet">' + highlightQuery(snippet, normalizedQuery) + '</div>';
+        + '<div class="snippet">' + highlightQuery(snippet, query) + '</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(normalizedQuery.toLowerCase());
+  const idx = lower.indexOf(query.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);
@@ -1047,11 +1038,11 @@ function snippetAround(text, query, len) {
 function highlightQuery(text, query) {
   if (!query) return escapeHtml(text);
   const escaped = escapeHtml(text);
-  const normalizedQuery = normalizeSearchQuery(query);
-  const queryEscaped = normalizedQuery.replace(/[.*+?^${}()|[\]\\]/g, '\\$&');
+  const queryEscaped = query.replace(/[.*+?^${}()|[\]\\]/g, '\\$&');
   const re = new RegExp('(' + queryEscaped + ')', 'gi');
   return escaped.replace(re, '<mark>$1</mark>');
 }
+
 // --- Logs ---
 
 const LOG_MAX_ENTRIES = 2000;

src/channels/web/static/index.html

@@ -5,11 +5,7 @@
   <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/[email protected]/lib/marked.umd.min.js"
-    integrity="sha384-pN9zSKOnTZwXRtYZAu0PBPEgR2B7DOC1aeLxQ33oJ0oy5iN1we6gm57xldM2irDG"
-    crossorigin="anonymous"
-  ></script>
+  <script src="https://cdn.jsdelivr.net/npm/marked/marked.min.js"></script>
 </head>
 <body>
   <!-- Auth Screen -->

src/cli/config.rs

@@ -48,6 +48,8 @@ pub enum ConfigCommand {
 /// Connects to the database to read/write settings. Falls back to disk
 /// if the database is not available.
 pub async fn run_config_command(cmd: ConfigCommand) -> anyhow::Result<()> {
+    let _ = dotenvy::dotenv();
+
     // Try to connect to the DB for settings access
     let db: Option<Arc<dyn crate::db::Database>> = match connect_db().await {
         Ok(d) => Some(d),
@@ -90,7 +92,7 @@ async fn load_settings(store: Option<&dyn crate::db::Database>) -> Settings {
             _ => {}
         }
     }
-    Settings::default()
+    Settings::load()
 }
 
 /// List all settings.
@@ -108,10 +110,10 @@ async fn list_settings(
     println!();
 
     for (key, value) in all {
-        if let Some(ref f) = filter
-            && !key.starts_with(f)
-        {
-            continue;
+        if let Some(ref f) = filter {
+            if !key.starts_with(f) {
+                continue;
+            }
         }
 
         let display_value = if value.len() > 60 {
@@ -153,17 +155,19 @@ async fn set_setting(
         .set(path, value)
         .map_err(|e| anyhow::anyhow!("{}", e))?;
 
-    let store = store.ok_or_else(|| {
-        anyhow::anyhow!("Database connection required to save settings. Check DATABASE_URL.")
-    })?;
-    let json_value = match serde_json::from_str::<serde_json::Value>(value) {
-        Ok(v) => v,
-        Err(_) => serde_json::Value::String(value.to_string()),
-    };
-    store
-        .set_setting(DEFAULT_USER_ID, path, &json_value)
-        .await
-        .map_err(|e| anyhow::anyhow!("Failed to save to database: {}", e))?;
+    // Save to DB if available, otherwise disk
+    if let Some(store) = store {
+        let json_value = match serde_json::from_str::<serde_json::Value>(value) {
+            Ok(v) => v,
+            Err(_) => serde_json::Value::String(value.to_string()),
+        };
+        store
+            .set_setting(DEFAULT_USER_ID, path, &json_value)
+            .await
+            .map_err(|e| anyhow::anyhow!("Failed to save to database: {}", e))?;
+    } else {
+        settings.save()?;
+    }
 
     println!("Set {} = {}", path, value);
     Ok(())
@@ -176,13 +180,17 @@ async fn reset_setting(store: Option<&dyn crate::db::Database>, path: &str) -> a
         .get(path)
         .ok_or_else(|| anyhow::anyhow!("Unknown setting: {}", path))?;
 
-    let store = store.ok_or_else(|| {
-        anyhow::anyhow!("Database connection required to reset settings. Check DATABASE_URL.")
-    })?;
-    store
-        .delete_setting(DEFAULT_USER_ID, path)
-        .await
-        .map_err(|e| anyhow::anyhow!("Failed to delete setting from database: {}", e))?;
+    // Delete from DB (falling back to default) or reset on disk
+    if let Some(store) = store {
+        store
+            .delete_setting(DEFAULT_USER_ID, path)
+            .await
+            .map_err(|e| anyhow::anyhow!("Failed to delete setting from database: {}", e))?;
+    } else {
+        let mut settings = Settings::load();
+        settings.reset(path).map_err(|e| anyhow::anyhow!("{}", e))?;
+        settings.save()?;
+    }
 
     println!("Reset {} to default: {}", path, default_value);
     Ok(())
@@ -192,13 +200,37 @@ async fn reset_setting(store: Option<&dyn crate::db::Database>, path: &str) -> a
 fn show_path(has_db: bool) -> anyhow::Result<()> {
     if has_db {
         println!("Settings stored in: database (settings table)");
+        println!(
+            "Bootstrap config:   {}",
+            crate::bootstrap::BootstrapConfig::default_path().display()
+        );
     } else {
-        println!("Settings stored in: PostgreSQL (not connected, using defaults)");
+        let path = Settings::default_path();
+        println!("Settings stored in: {} (disk fallback)", path.display());
+
+        if path.exists() {
+            let metadata = std::fs::metadata(&path)?;
+            println!("  Size: {} bytes", metadata.len());
+            if let Ok(modified) = metadata.modified() {
+                use std::time::SystemTime;
+                let duration = SystemTime::now()
+                    .duration_since(modified)
+                    .unwrap_or_default();
+                let secs = duration.as_secs();
+                if secs < 60 {
+                    println!("  Modified: {} seconds ago", secs);
+                } else if secs < 3600 {
+                    println!("  Modified: {} minutes ago", secs / 60);
+                } else if secs < 86400 {
+                    println!("  Modified: {} hours ago", secs / 3600);
+                } else {
+                    println!("  Modified: {} days ago", secs / 86400);
+                }
+            }
+        } else {
+            println!("  (does not exist, using defaults)");
+        }
     }
-    println!(
-        "Env config:         {}",
-        crate::bootstrap::ironclaw_env_path().display()
-    );
 
     Ok(())
 }

src/cli/mod.rs

@@ -12,7 +12,6 @@
 mod config;
 mod mcp;
 pub mod memory;
-pub mod oauth_defaults;
 mod pairing;
 pub mod status;
 mod tool;

src/cli/oauth_defaults.rs

@@ -1,342 +0,0 @@
-//! Shared OAuth infrastructure: built-in credentials, callback server, landing pages.
-//!
-//! Every OAuth flow in the codebase (WASM tool auth, MCP server auth, NEAR AI login)
-//! uses the same callback port, landing page, and listener logic from this module.
-//!
-//! # Built-in Credentials
-//!
-//! Many CLI tools (gcloud, rclone, gdrive) ship with default OAuth credentials
-//! so users don't need to register their own OAuth app. Google explicitly
-//! documents that client_secret for "Desktop App" / "Installed App" types
-//! is NOT actually secret.
-//!
-//! Default credentials are hardcoded below. They can be overridden at:
-//!
-//! - **Compile time**: Set IRONCLAW_GOOGLE_CLIENT_ID / IRONCLAW_GOOGLE_CLIENT_SECRET
-//!   env vars before building to replace the hardcoded defaults.
-//! - **Runtime**: Users can set GOOGLE_OAUTH_CLIENT_ID / GOOGLE_OAUTH_CLIENT_SECRET
-//!   env vars, which take priority over built-in defaults.
-
-use std::time::Duration;
-
-use tokio::io::{AsyncBufReadExt, AsyncWriteExt, BufReader};
-use tokio::net::TcpListener;
-
-// ── Built-in credentials ────────────────────────────────────────────────
-
-pub struct OAuthCredentials {
-    pub client_id: &'static str,
-    pub client_secret: &'static str,
-}
-
-/// Google OAuth "Desktop App" credentials, shared across all Google tools.
-/// Compile-time env vars override the hardcoded defaults below.
-const GOOGLE_CLIENT_ID: &str = match option_env!("IRONCLAW_GOOGLE_CLIENT_ID") {
-    Some(v) => v,
-    None => "564604149681-efo25d43rs85v0tibdepsmdv5dsrhhr0.apps.googleusercontent.com",
-};
-const GOOGLE_CLIENT_SECRET: &str = match option_env!("IRONCLAW_GOOGLE_CLIENT_SECRET") {
-    Some(v) => v,
-    None => "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",
-};
-
-/// Returns built-in OAuth credentials for a provider, keyed by secret_name.
-///
-/// The secret_name comes from the tool's capabilities.json `auth.secret_name` field.
-/// Returns `None` if no built-in credentials are configured for that provider.
-pub fn builtin_credentials(secret_name: &str) -> Option<OAuthCredentials> {
-    match secret_name {
-        "google_oauth_token" => Some(OAuthCredentials {
-            client_id: GOOGLE_CLIENT_ID,
-            client_secret: GOOGLE_CLIENT_SECRET,
-        }),
-        _ => None,
-    }
-}
-
-// ── Shared callback server ──────────────────────────────────────────────
-
-/// Fixed port for all OAuth callbacks.
-///
-/// Every redirect URI registered with providers must use this port:
-/// `http://localhost:9876/callback` (or `/auth/callback` for NEAR AI).
-pub const OAUTH_CALLBACK_PORT: u16 = 9876;
-
-/// Error from the OAuth callback listener.
-#[derive(Debug, thiserror::Error)]
-pub enum OAuthCallbackError {
-    #[error("Port {0} is in use (another auth flow running?): {1}")]
-    PortInUse(u16, String),
-
-    #[error("Authorization denied by user")]
-    Denied,
-
-    #[error("Timed out waiting for authorization")]
-    Timeout,
-
-    #[error("IO error: {0}")]
-    Io(String),
-}
-
-/// Bind the OAuth callback listener on the fixed port.
-///
-/// Binds to IPv4 `127.0.0.1` first because callback URLs use `127.0.0.1`
-/// explicitly (e.g., NEAR AI redirects to `http://127.0.0.1:9876/auth/callback`).
-/// Falls back to IPv6 `[::1]` only if IPv4 binding fails for a reason other
-/// than `AddrInUse`. If the port is already occupied, fails immediately.
-pub async fn bind_callback_listener() -> Result<TcpListener, OAuthCallbackError> {
-    let ipv4_addr = format!("127.0.0.1:{}", OAUTH_CALLBACK_PORT);
-    match TcpListener::bind(&ipv4_addr).await {
-        Ok(listener) => return Ok(listener),
-        Err(e) if e.kind() == std::io::ErrorKind::AddrInUse => {
-            return Err(OAuthCallbackError::PortInUse(
-                OAUTH_CALLBACK_PORT,
-                e.to_string(),
-            ));
-        }
-        Err(_) => {
-            // IPv4 not available, fall back to IPv6
-        }
-    }
-    TcpListener::bind(format!("[::1]:{}", OAUTH_CALLBACK_PORT))
-        .await
-        .map_err(|e| {
-            if e.kind() == std::io::ErrorKind::AddrInUse {
-                OAuthCallbackError::PortInUse(OAUTH_CALLBACK_PORT, e.to_string())
-            } else {
-                OAuthCallbackError::Io(e.to_string())
-            }
-        })
-}
-
-/// Wait for an OAuth callback and extract a query parameter value.
-///
-/// Listens for a GET request matching `path_prefix` (e.g., "/callback" or "/auth/callback"),
-/// extracts the value of `param_name` (e.g., "code" or "token"), and shows a branded
-/// landing page using `display_name` (e.g., "Google", "Notion", "NEAR AI").
-///
-/// Times out after 5 minutes.
-pub async fn wait_for_callback(
-    listener: TcpListener,
-    path_prefix: &str,
-    param_name: &str,
-    display_name: &str,
-) -> Result<String, OAuthCallbackError> {
-    let path_prefix = path_prefix.to_string();
-    let param_name = param_name.to_string();
-    let display_name = display_name.to_string();
-
-    tokio::time::timeout(Duration::from_secs(300), async move {
-        loop {
-            let (mut socket, _) = listener
-                .accept()
-                .await
-                .map_err(|e| OAuthCallbackError::Io(e.to_string()))?;
-
-            let mut reader = BufReader::new(&mut socket);
-            let mut request_line = String::new();
-            reader
-                .read_line(&mut request_line)
-                .await
-                .map_err(|e| OAuthCallbackError::Io(e.to_string()))?;
-
-            if let Some(path) = request_line.split_whitespace().nth(1)
-                && path.starts_with(&path_prefix)
-                && let Some(query) = path.split('?').nth(1)
-            {
-                // Check for error first
-                if query.contains("error=") {
-                    let html = landing_html(&display_name, false);
-                    let response = format!(
-                        "HTTP/1.1 400 Bad Request\r\n\
-                         Content-Type: text/html; charset=utf-8\r\n\
-                         Connection: close\r\n\
-                         \r\n\
-                         {}",
-                        html
-                    );
-                    let _ = socket.write_all(response.as_bytes()).await;
-                    return Err(OAuthCallbackError::Denied);
-                }
-
-                // Look for the target parameter
-                for param in query.split('&') {
-                    let parts: Vec<&str> = param.splitn(2, '=').collect();
-                    if parts.len() == 2 && parts[0] == param_name {
-                        let value = urlencoding::decode(parts[1])
-                            .unwrap_or_else(|_| parts[1].into())
-                            .into_owned();
-
-                        let html = landing_html(&display_name, true);
-                        let response = format!(
-                            "HTTP/1.1 200 OK\r\n\
-                             Content-Type: text/html; charset=utf-8\r\n\
-                             Connection: close\r\n\
-                             \r\n\
-                             {}",
-                            html
-                        );
-                        let _ = socket.write_all(response.as_bytes()).await;
-                        let _ = socket.shutdown().await;
-
-                        return Ok(value);
-                    }
-                }
-            }
-
-            // Not the callback we're looking for
-            let response = "HTTP/1.1 404 Not Found\r\nConnection: close\r\n\r\n";
-            let _ = socket.write_all(response.as_bytes()).await;
-        }
-    })
-    .await
-    .map_err(|_| OAuthCallbackError::Timeout)?
-}
-
-/// Escape a string for safe interpolation into HTML content.
-fn html_escape(s: &str) -> String {
-    let mut out = String::with_capacity(s.len());
-    for c in s.chars() {
-        match c {
-            '&' => out.push_str("&amp;"),
-            '<' => out.push_str("&lt;"),
-            '>' => out.push_str("&gt;"),
-            '"' => out.push_str("&quot;"),
-            '\'' => out.push_str("&#x27;"),
-            _ => out.push(c),
-        }
-    }
-    out
-}
-
-/// HTML landing page shown in the browser after an OAuth redirect.
-pub fn landing_html(provider_name: &str, success: bool) -> String {
-    let safe_name = html_escape(provider_name);
-    let (icon, heading, subtitle, accent) = if success {
-        (
-            r##"<div style="width:64px;height:64px;border-radius:50%;background:#22c55e;display:flex;align-items:center;justify-content:center;margin:0 auto 24px">
-                <svg width="32" height="32" viewBox="0 0 24 24" fill="none" stroke="#fff" stroke-width="3" stroke-linecap="round" stroke-linejoin="round"><polyline points="20 6 9 17 4 12"/></svg>
-              </div>"##,
-            format!("{} Connected", safe_name),
-            "You can close this window and return to your terminal.",
-            "#22c55e",
-        )
-    } else {
-        (
-            r##"<div style="width:64px;height:64px;border-radius:50%;background:#ef4444;display:flex;align-items:center;justify-content:center;margin:0 auto 24px">
-                <svg width="32" height="32" viewBox="0 0 24 24" fill="none" stroke="#fff" stroke-width="3" stroke-linecap="round" stroke-linejoin="round"><line x1="18" y1="6" x2="6" y2="18"/><line x1="6" y1="6" x2="18" y2="18"/></svg>
-              </div>"##,
-            "Authorization Failed".to_string(),
-            "The request was denied. You can close this window and try again.",
-            "#ef4444",
-        )
-    };
-
-    format!(
-        r#"<!DOCTYPE html>
-<html lang="en">
-<head>
-<meta charset="utf-8">
-<meta name="viewport" content="width=device-width,initial-scale=1">
-<title>IronClaw - {heading}</title>
-<style>
-  * {{ margin:0; padding:0; box-sizing:border-box }}
-  body {{
-    font-family: -apple-system, BlinkMacSystemFont, "Segoe UI", Roboto, Helvetica, Arial, sans-serif;
-    background: #0a0a0a;
-    color: #e5e5e5;
-    display: flex;
-    justify-content: center;
-    align-items: center;
-    min-height: 100vh;
-  }}
-  .card {{
-    text-align: center;
-    padding: 48px 40px;
-    max-width: 420px;
-    border: 1px solid #262626;
-    border-radius: 16px;
-    background: #141414;
-  }}
-  h1 {{
-    font-size: 22px;
-    font-weight: 600;
-    margin-bottom: 8px;
-    color: #fafafa;
-  }}
-  p {{
-    font-size: 14px;
-    color: #a3a3a3;
-    line-height: 1.5;
-  }}
-  .accent {{ color: {accent}; }}
-  .brand {{
-    margin-top: 32px;
-    font-size: 12px;
-    color: #525252;
-    letter-spacing: 0.5px;
-    text-transform: uppercase;
-  }}
-</style>
-</head>
-<body>
-  <div class="card">
-    {icon}
-    <h1>{heading}</h1>
-    <p>{subtitle}</p>
-    <div class="brand">IronClaw</div>
-  </div>
-</body>
-</html>"#,
-        heading = heading,
-        icon = icon,
-        subtitle = subtitle,
-        accent = accent,
-    )
-}
-
-#[cfg(test)]
-mod tests {
-    use crate::cli::oauth_defaults::{builtin_credentials, landing_html};
-
-    #[test]
-    fn test_unknown_provider_returns_none() {
-        assert!(builtin_credentials("unknown_token").is_none());
-    }
-
-    #[test]
-    fn test_google_returns_based_on_compile_env() {
-        let creds = builtin_credentials("google_oauth_token");
-        assert!(creds.is_some());
-        let creds = creds.unwrap();
-        assert!(!creds.client_id.is_empty());
-        assert!(!creds.client_secret.is_empty());
-    }
-
-    #[test]
-    fn test_landing_html_success_contains_key_elements() {
-        let html = landing_html("Google", true);
-        assert!(html.contains("Google Connected"));
-        assert!(html.contains("charset"));
-        assert!(html.contains("IronClaw"));
-        assert!(html.contains("#22c55e")); // green accent
-        assert!(!html.contains("Failed"));
-    }
-
-    #[test]
-    fn test_landing_html_escapes_provider_name() {
-        let html = landing_html("<script>alert(1)</script>", true);
-        assert!(!html.contains("<script>"));
-        assert!(html.contains("&lt;script&gt;"));
-    }
-
-    #[test]
-    fn test_landing_html_error_contains_key_elements() {
-        let html = landing_html("Notion", false);
-        assert!(html.contains("Authorization Failed"));
-        assert!(html.contains("charset"));
-        assert!(html.contains("IronClaw"));
-        assert!(html.contains("#ef4444")); // red accent
-        assert!(!html.contains("Connected"));
-    }
-}

src/cli/status.rs

@@ -9,7 +9,7 @@ use crate::settings::Settings;
 
 /// Run the status command, printing system health info.
 pub async fn run_status_command() -> anyhow::Result<()> {
-    let settings = Settings::default();
+    let settings = Settings::load();
 
     println!("IronClaw Status");
     println!("===============\n");
@@ -22,36 +22,16 @@ pub async fn run_status_command() -> anyhow::Result<()> {
     );
 
     // Database
+    let db_url_set = settings.database_url.is_some() || std::env::var("DATABASE_URL").is_ok();
     print!("  Database:    ");
-    let db_backend = std::env::var("DATABASE_BACKEND")
-        .ok()
-        .unwrap_or_else(|| "postgres".to_string());
-    match db_backend.as_str() {
-        "libsql" | "turso" | "sqlite" => {
-            let path = std::env::var("LIBSQL_PATH")
-                .map(std::path::PathBuf::from)
-                .unwrap_or_else(|_| crate::config::default_libsql_path());
-            if path.exists() {
-                let turso = if std::env::var("LIBSQL_URL").is_ok() {
-                    " + Turso sync"
-                } else {
-                    ""
-                };
-                println!("libSQL ({}{})", path.display(), turso);
-            } else {
-                println!("libSQL (file missing: {})", path.display());
-            }
-        }
-        _ => {
-            if std::env::var("DATABASE_URL").is_ok() {
-                match check_database().await {
-                    Ok(()) => println!("connected (PostgreSQL)"),
-                    Err(e) => println!("error ({})", e),
-                }
-            } else {
-                println!("not configured");
-            }
+    if db_url_set {
+        // Try to connect
+        match check_database().await {
+            Ok(()) => println!("connected"),
+            Err(e) => println!("error ({})", e),
         }
+    } else {
+        println!("not configured");
     }
 
     // Session / Auth
@@ -63,17 +43,15 @@ pub async fn run_status_command() -> anyhow::Result<()> {
         println!("not found (run `ironclaw onboard`)");
     }
 
-    // Secrets (auto-detect from env only; skip keychain probe to avoid
-    // triggering macOS system password dialogs on a simple status check)
+    // Secrets
     print!("  Secrets:     ");
-    if std::env::var("SECRETS_MASTER_KEY").is_ok() {
-        println!("configured (env)");
+    let secrets_configured = settings.secrets_master_key_source != crate::settings::KeySource::None
+        || std::env::var("SECRETS_MASTER_KEY").is_ok()
+        || crate::secrets::keychain::has_master_key().await;
+    if secrets_configured {
+        println!("configured ({:?})", settings.secrets_master_key_source);
     } else {
-        // We don't probe the keychain here because get_generic_password()
-        // triggers macOS unlock+authorization dialogs, which is bad UX for
-        // a read-only status command. If onboarding completed with keychain
-        // storage, the key is there; we just can't cheaply verify it.
-        println!("env not set (keychain may be configured)");
+        println!("not configured");
     }
 
     // Embeddings
@@ -151,18 +129,20 @@ pub async fn run_status_command() -> anyhow::Result<()> {
         Err(_) => println!("none configured"),
     }
 
-    // Config path
-    println!(
-        "\n  Config:      {}",
-        crate::bootstrap::ironclaw_env_path().display()
-    );
+    // Settings path
+    println!("\n  Settings:    {}", Settings::default_path().display());
 
     Ok(())
 }
 
 #[cfg(feature = "postgres")]
 async fn check_database() -> anyhow::Result<()> {
-    let url = std::env::var("DATABASE_URL").map_err(|_| anyhow::anyhow!("DATABASE_URL not set"))?;
+    let _ = dotenvy::dotenv();
+    let settings = Settings::load();
+    let url = std::env::var("DATABASE_URL")
+        .ok()
+        .or(settings.database_url)
+        .ok_or_else(|| anyhow::anyhow!("no URL"))?;
 
     let config: deadpool_postgres::Config = deadpool_postgres::Config {
         url: Some(url),

src/cli/tool.rs

@@ -423,11 +423,11 @@ async fn extract_crate_name(cargo_toml: &Path) -> anyhow::Result<String> {
     // Simple TOML parsing for [package] name
     for line in content.lines() {
         let line = line.trim();
-        if line.starts_with("name")
-            && let Some((_, value)) = line.split_once('=')
-        {
-            let name = value.trim().trim_matches('"').trim_matches('\'');
-            return Ok(name.to_string());
+        if line.starts_with("name") {
+            if let Some((_, value)) = line.split_once('=') {
+                let name = value.trim().trim_matches('"').trim_matches('\'');
+                return Ok(name.to_string());
+            }
         }
     }
 
@@ -491,10 +491,10 @@ async fn list_tools(dir: Option<PathBuf>, verbose: bool) -> anyhow::Result<()> {
 
             if has_caps {
                 let caps_path = path.with_extension("capabilities.json");
-                if let Ok(content) = fs::read_to_string(&caps_path).await
-                    && let Ok(caps) = CapabilitiesFile::from_json(&content)
-                {
-                    print_capabilities_summary(&caps);
+                if let Ok(content) = fs::read_to_string(&caps_path).await {
+                    if let Ok(caps) = CapabilitiesFile::from_json(&content) {
+                        print_capabilities_summary(&caps);
+                    }
                 }
             }
             println!();
@@ -607,16 +607,16 @@ fn print_capabilities_summary(caps: &CapabilitiesFile) {
         }
     }
 
-    if let Some(ref secrets) = caps.secrets
-        && !secrets.allowed_names.is_empty()
-    {
-        parts.push(format!("secrets: {}", secrets.allowed_names.len()));
+    if let Some(ref secrets) = caps.secrets {
+        if !secrets.allowed_names.is_empty() {
+            parts.push(format!("secrets: {}", secrets.allowed_names.len()));
+        }
     }
 
-    if let Some(ref ws) = caps.workspace
-        && !ws.allowed_prefixes.is_empty()
-    {
-        parts.push("workspace: read".to_string());
+    if let Some(ref ws) = caps.workspace {
+        if !ws.allowed_prefixes.is_empty() {
+            parts.push("workspace: read".to_string());
+        }
     }
 
     if !parts.is_empty() {
@@ -653,30 +653,30 @@ fn print_capabilities_detail(caps: &CapabilitiesFile) {
         }
     }
 
-    if let Some(ref secrets) = caps.secrets
-        && !secrets.allowed_names.is_empty()
-    {
-        println!("  Secrets (existence check only):");
-        for name in &secrets.allowed_names {
-            println!("    {}", name);
+    if let Some(ref secrets) = caps.secrets {
+        if !secrets.allowed_names.is_empty() {
+            println!("  Secrets (existence check only):");
+            for name in &secrets.allowed_names {
+                println!("    {}", name);
+            }
         }
     }
 
-    if let Some(ref tool_invoke) = caps.tool_invoke
-        && !tool_invoke.aliases.is_empty()
-    {
-        println!("  Tool aliases:");
-        for (alias, real_name) in &tool_invoke.aliases {
-            println!("    {} -> {}", alias, real_name);
+    if let Some(ref tool_invoke) = caps.tool_invoke {
+        if !tool_invoke.aliases.is_empty() {
+            println!("  Tool aliases:");
+            for (alias, real_name) in &tool_invoke.aliases {
+                println!("    {} -> {}", alias, real_name);
+            }
         }
     }
 
-    if let Some(ref ws) = caps.workspace
-        && !ws.allowed_prefixes.is_empty()
-    {
-        println!("  Workspace read prefixes:");
-        for prefix in &ws.allowed_prefixes {
-            println!("    {}", prefix);
+    if let Some(ref ws) = caps.workspace {
+        if !ws.allowed_prefixes.is_empty() {
+            println!("  Workspace read prefixes:");
+            for prefix in &ws.allowed_prefixes {
+                println!("    {}", prefix);
+            }
         }
     }
 }
@@ -802,100 +802,48 @@ async fn auth_tool(name: String, dir: Option<PathBuf>, user_id: String) -> anyho
     }
 
     // Check for environment variable
-    if let Some(ref env_var) = auth.env_var
-        && let Ok(token) = std::env::var(env_var)
-        && !token.is_empty()
-    {
-        println!("  Found {} in environment.", env_var);
-        println!();
+    if let Some(ref env_var) = auth.env_var {
+        if let Ok(token) = std::env::var(env_var) {
+            if !token.is_empty() {
+                println!("  Found {} in environment.", env_var);
+                println!();
 
-        // Validate if endpoint is provided
-        if let Some(ref validation) = auth.validation_endpoint {
-            print!("  Validating token...");
-            std::io::stdout().flush()?;
+                // Validate if endpoint is provided
+                if let Some(ref validation) = auth.validation_endpoint {
+                    print!("  Validating token...");
+                    std::io::stdout().flush()?;
 
-            match validate_token(&token, validation, &auth.secret_name).await {
-                Ok(()) => {
-                    println!(" ✓");
-                }
-                Err(e) => {
-                    println!(" ✗");
-                    println!("  Validation failed: {}", e);
-                    println!();
-                    println!("  Falling back to manual entry...");
-                    return auth_tool_manual(secrets_store.as_ref(), &user_id, &auth).await;
+                    match validate_token(&token, validation, &auth.secret_name).await {
+                        Ok(()) => {
+                            println!(" ✓");
+                        }
+                        Err(e) => {
+                            println!(" ✗");
+                            println!("  Validation failed: {}", e);
+                            println!();
+                            println!("  Falling back to manual entry...");
+                            return auth_tool_manual(secrets_store.as_ref(), &user_id, &auth).await;
+                        }
+                    }
                 }
+
+                // Save the token
+                save_token(secrets_store.as_ref(), &user_id, &auth, &token).await?;
+                print_success(display_name);
+                return Ok(());
             }
         }
-
-        // Save the token
-        save_token(secrets_store.as_ref(), &user_id, &auth, &token, None, None).await?;
-        print_success(display_name);
-        return Ok(());
     }
 
     // Check for OAuth configuration
     if let Some(ref oauth) = auth.oauth {
-        // For providers with shared tokens (e.g., all Google tools share google_oauth_token),
-        // combine scopes from all installed tools so one auth covers everything.
-        let combined = combine_provider_scopes(&tools_dir, &auth.secret_name, oauth).await;
-        if combined.scopes.len() > oauth.scopes.len() {
-            let extra = combined.scopes.len() - oauth.scopes.len();
-            println!(
-                "  Including scopes from {} other installed tool(s) sharing this credential.",
-                extra
-            );
-            println!();
-        }
-        return auth_tool_oauth(secrets_store.as_ref(), &user_id, &auth, &combined).await;
+        return auth_tool_oauth(secrets_store.as_ref(), &user_id, &auth, oauth).await;
     }
 
     // Fall back to manual entry
     auth_tool_manual(secrets_store.as_ref(), &user_id, &auth).await
 }
 
-/// Scan the tools directory for all capabilities files sharing the same secret_name
-/// and combine their OAuth scopes. This way, authing any Google tool requests scopes
-/// for ALL installed Google tools, so one login covers everything.
-async fn combine_provider_scopes(
-    tools_dir: &Path,
-    secret_name: &str,
-    base_oauth: &crate::tools::wasm::OAuthConfigSchema,
-) -> crate::tools::wasm::OAuthConfigSchema {
-    let mut all_scopes: std::collections::HashSet<String> =
-        base_oauth.scopes.iter().cloned().collect();
-
-    if let Ok(mut entries) = tokio::fs::read_dir(tools_dir).await {
-        while let Ok(Some(entry)) = entries.next_entry().await {
-            let path = entry.path();
-            if path.extension().and_then(|e| e.to_str()) != Some("json") {
-                continue;
-            }
-            let name = path
-                .file_name()
-                .and_then(|n| n.to_str())
-                .unwrap_or_default();
-            if !name.ends_with(".capabilities.json") {
-                continue;
-            }
-
-            if let Ok(content) = tokio::fs::read_to_string(&path).await
-                && let Ok(caps) = CapabilitiesFile::from_json(&content)
-                && let Some(auth) = &caps.auth
-                && auth.secret_name == secret_name
-                && let Some(oauth) = &auth.oauth
-            {
-                all_scopes.extend(oauth.scopes.iter().cloned());
-            }
-        }
-    }
-
-    let mut combined = base_oauth.clone();
-    combined.scopes = all_scopes.into_iter().collect();
-    combined.scopes.sort(); // deterministic ordering
-    combined
-}
-
 /// OAuth browser-based login flow.
 async fn auth_tool_oauth(
     store: &(dyn SecretsStore + Send + Sync),
@@ -906,14 +854,12 @@ async fn auth_tool_oauth(
     use base64::{Engine, engine::general_purpose::URL_SAFE_NO_PAD};
     use rand::RngCore;
     use sha2::{Digest, Sha256};
-
-    use crate::cli::oauth_defaults::{self, OAUTH_CALLBACK_PORT};
+    use tokio::io::{AsyncBufReadExt, AsyncWriteExt, BufReader};
+    use tokio::net::TcpListener;
 
     let display_name = auth.display_name.as_deref().unwrap_or(&auth.secret_name);
 
-    // Get client_id: capabilities file > runtime env var > built-in defaults
-    let builtin = oauth_defaults::builtin_credentials(&auth.secret_name);
-
+    // Get client_id from config or env
     let client_id = oauth
         .client_id
         .clone()
@@ -923,32 +869,41 @@ async fn auth_tool_oauth(
                 .as_ref()
                 .and_then(|env| std::env::var(env).ok())
         })
-        .or_else(|| builtin.as_ref().map(|c| c.client_id.to_string()))
         .ok_or_else(|| {
             anyhow::anyhow!(
                 "OAuth client_id not configured.\n\
-                 Set {} env var, or build with IRONCLAW_GOOGLE_CLIENT_ID.",
-                oauth.client_id_env.as_deref().unwrap_or("the client_id")
+                 Set it in the capabilities file or via environment variable."
             )
         })?;
 
-    // Get client_secret: capabilities file > runtime env var > built-in defaults
-    let client_secret = oauth
-        .client_secret
-        .clone()
-        .or_else(|| {
-            oauth
-                .client_secret_env
-                .as_ref()
-                .and_then(|env| std::env::var(env).ok())
-        })
-        .or_else(|| builtin.as_ref().map(|c| c.client_secret.to_string()));
+    // Get client_secret if provided
+    let client_secret = oauth.client_secret.clone().or_else(|| {
+        oauth
+            .client_secret_env
+            .as_ref()
+            .and_then(|env| std::env::var(env).ok())
+    });
 
     println!("  Starting OAuth authentication...");
     println!();
 
-    let listener = oauth_defaults::bind_callback_listener().await?;
-    let redirect_uri = format!("http://localhost:{}/callback", OAUTH_CALLBACK_PORT);
+    // Find an available port for the callback
+    let mut listener = None;
+    let mut port = 0;
+
+    for p in 9876..=9886 {
+        match TcpListener::bind(format!("127.0.0.1:{}", p)).await {
+            Ok(l) => {
+                listener = Some(l);
+                port = p;
+                break;
+            }
+            Err(_) => continue,
+        }
+    }
+
+    let listener = listener.ok_or_else(|| anyhow::anyhow!("Could not find available port"))?;
+    let redirect_uri = format!("http://localhost:{}/callback", port);
 
     // Generate PKCE verifier and challenge
     let (code_verifier, code_challenge) = if oauth.use_pkce {
@@ -1007,8 +962,65 @@ async fn auth_tool_oauth(
 
     println!("  Waiting for authorization...");
 
-    let code =
-        oauth_defaults::wait_for_callback(listener, "/callback", "code", display_name).await?;
+    // Wait for callback with timeout
+    let timeout = std::time::Duration::from_secs(300);
+    let code = tokio::time::timeout(timeout, async {
+        loop {
+            let (mut socket, _) = listener.accept().await?;
+
+            let mut reader = BufReader::new(&mut socket);
+            let mut request_line = String::new();
+            reader.read_line(&mut request_line).await?;
+
+            // Parse GET /callback?code=xxx HTTP/1.1
+            if let Some(path) = request_line.split_whitespace().nth(1) {
+                if path.starts_with("/callback") {
+                    if let Some(query) = path.split('?').nth(1) {
+                        for param in query.split('&') {
+                            let parts: Vec<&str> = param.splitn(2, '=').collect();
+                            if parts.len() == 2 && parts[0] == "code" {
+                                let code = urlencoding::decode(parts[1])
+                                    .unwrap_or_else(|_| parts[1].into())
+                                    .into_owned();
+
+                                // Send success response
+                                let response = format!(
+                                    "HTTP/1.1 200 OK\r\n\
+                                     Content-Type: text/html\r\n\
+                                     \r\n\
+                                     <!DOCTYPE html><html><body style=\"font-family: sans-serif; \
+                                     display: flex; justify-content: center; align-items: center; \
+                                     height: 100vh; margin: 0; background: #191919; color: white;\">\
+                                     <div style=\"text-align: center;\">\
+                                     <h1>✓ {} Connected!</h1>\
+                                     <p>You can close this window.</p>\
+                                     </div></body></html>",
+                                    display_name
+                                );
+                                let _ = socket.write_all(response.as_bytes()).await;
+                                let _ = socket.shutdown().await;
+
+                                return Ok::<_, anyhow::Error>(code);
+                            }
+                        }
+
+                        // Check for error
+                        if query.contains("error=") {
+                            let response =
+                                "HTTP/1.1 400 Bad Request\r\n\r\nAuthorization denied";
+                            let _ = socket.write_all(response.as_bytes()).await;
+                            return Err(anyhow::anyhow!("Authorization denied by user"));
+                        }
+                    }
+                }
+            }
+
+            let response = "HTTP/1.1 404 Not Found\r\n\r\n";
+            let _ = socket.write_all(response.as_bytes()).await;
+        }
+    })
+    .await
+    .map_err(|_| anyhow::anyhow!("Timed out waiting for authorization"))??;
 
     println!();
     println!("  Exchanging code for token...");
@@ -1059,19 +1071,8 @@ async fn auth_tool_oauth(
             )
         })?;
 
-    let refresh_token = token_data.get("refresh_token").and_then(|v| v.as_str());
-    let expires_in = token_data.get("expires_in").and_then(|v| v.as_u64());
-
-    // Save the token (with refresh token and expiry if provided)
-    save_token(
-        store,
-        user_id,
-        auth,
-        access_token,
-        refresh_token,
-        expires_in,
-    )
-    .await?;
+    // Save the token
+    save_token(store, user_id, auth, access_token).await?;
 
     // Extract any additional info for display
     let workspace_name = token_data
@@ -1173,8 +1174,8 @@ async fn auth_tool_manual(
         }
     }
 
-    // Save the token (manual path: no refresh token or expiry)
-    save_token(store, user_id, auth, &token, None, None).await?;
+    // Save the token
+    save_token(store, user_id, auth, &token).await?;
     print_success(display_name);
     Ok(())
 }
@@ -1265,16 +1266,11 @@ async fn validate_token(
 }
 
 /// Save token to secrets store.
-///
-/// Optionally stores a refresh token (as `{secret_name}_refresh_token`) and
-/// sets `expires_at` on the access token so the runtime can auto-refresh.
 async fn save_token(
     store: &(dyn SecretsStore + Send + Sync),
     user_id: &str,
     auth: &crate::tools::wasm::AuthCapabilitySchema,
     token: &str,
-    refresh_token: Option<&str>,
-    expires_in: Option<u64>,
 ) -> anyhow::Result<()> {
     let mut params = CreateSecretParams::new(&auth.secret_name, token);
 
@@ -1282,29 +1278,11 @@ async fn save_token(
         params = params.with_provider(provider);
     }
 
-    if let Some(secs) = expires_in {
-        let expires_at = chrono::Utc::now() + chrono::Duration::seconds(secs as i64);
-        params = params.with_expiry(expires_at);
-    }
-
     store
         .create(user_id, params)
         .await
         .map_err(|e| anyhow::anyhow!("Failed to save token: {}", e))?;
 
-    // Store refresh token separately (no expiry, it's long-lived)
-    if let Some(rt) = refresh_token {
-        let refresh_name = format!("{}_refresh_token", auth.secret_name);
-        let mut refresh_params = CreateSecretParams::new(&refresh_name, rt);
-        if let Some(ref provider) = auth.provider {
-            refresh_params = refresh_params.with_provider(provider);
-        }
-        store
-            .create(user_id, refresh_params)
-            .await
-            .map_err(|e| anyhow::anyhow!("Failed to save refresh token: {}", e))?;
-    }
-
     Ok(())
 }
 

src/config.rs

@@ -1,13 +1,11 @@
 //! Configuration for IronClaw.
 //!
 //! Settings are loaded with priority: env var > database > default.
-//! `DATABASE_URL` lives in `~/.ironclaw/.env` (loaded via dotenvy early
-//! in startup). Everything else comes from env vars, the DB settings
-//! table, or auto-detection.
+//! The database replaces the old `settings.json` file for all settings
+//! except the 4 bootstrap fields (database_url, pool_size, secrets key
+//! source, onboard_completed) which live in `~/.ironclaw/bootstrap.json`.
 
-use std::collections::HashMap;
 use std::path::PathBuf;
-use std::sync::OnceLock;
 use std::time::Duration;
 
 use secrecy::{ExposeSecret, SecretString};
@@ -15,13 +13,6 @@ use secrecy::{ExposeSecret, SecretString};
 use crate::error::ConfigError;
 use crate::settings::Settings;
 
-/// Thread-safe overlay for injected env vars (secrets loaded from DB).
-///
-/// Used by `inject_llm_keys_from_secrets()` to make API keys available to
-/// `optional_env()` without unsafe `set_var` calls. `optional_env()` checks
-/// real env vars first, then falls back to this overlay.
-static INJECTED_VARS: OnceLock<HashMap<String, String>> = OnceLock::new();
-
 /// Main configuration for the agent.
 #[derive(Debug, Clone)]
 pub struct Config {
@@ -49,9 +40,9 @@ impl Config {
     pub async fn from_db(
         store: &dyn crate::db::Database,
         user_id: &str,
+        bootstrap: &crate::bootstrap::BootstrapConfig,
     ) -> Result<Self, ConfigError> {
         let _ = dotenvy::dotenv();
-        crate::bootstrap::load_ironclaw_env();
 
         // Load all settings from DB into a Settings struct
         let db_settings = match store.get_all_settings(user_id).await {
@@ -62,7 +53,7 @@ impl Config {
             }
         };
 
-        Self::build(&db_settings).await
+        Self::build(bootstrap, &db_settings).await
     }
 
     /// Load configuration from environment variables only (no database).
@@ -70,20 +61,20 @@ impl Config {
     /// Used during early startup before the database is connected,
     /// and by CLI commands that don't have DB access.
     /// Falls back to legacy `settings.json` on disk if present.
-    ///
-    /// Loads both `./.env` (standard, higher priority) and `~/.ironclaw/.env`
-    /// (lower priority) via dotenvy, which never overwrites existing vars.
     pub async fn from_env() -> Result<Self, ConfigError> {
         let _ = dotenvy::dotenv();
-        crate::bootstrap::load_ironclaw_env();
+        let bootstrap = crate::bootstrap::BootstrapConfig::load();
         let settings = Settings::load();
-        Self::build(&settings).await
+        Self::build(&bootstrap, &settings).await
     }
 
-    /// Build config from settings (shared by from_env and from_db).
-    async fn build(settings: &Settings) -> Result<Self, ConfigError> {
+    /// Build config from bootstrap + settings (shared by from_env and from_db).
+    async fn build(
+        bootstrap: &crate::bootstrap::BootstrapConfig,
+        settings: &Settings,
+    ) -> Result<Self, ConfigError> {
         Ok(Self {
-            database: DatabaseConfig::resolve()?,
+            database: DatabaseConfig::resolve(bootstrap)?,
             llm: LlmConfig::resolve(settings)?,
             embeddings: EmbeddingsConfig::resolve(settings)?,
             tunnel: TunnelConfig::resolve(settings)?,
@@ -91,7 +82,7 @@ impl Config {
             agent: AgentConfig::resolve(settings)?,
             safety: SafetyConfig::resolve()?,
             wasm: WasmConfig::resolve()?,
-            secrets: SecretsConfig::resolve().await?,
+            secrets: SecretsConfig::resolve(bootstrap).await?,
             builder: BuilderModeConfig::resolve()?,
             heartbeat: HeartbeatConfig::resolve(settings)?,
             routines: RoutineConfig::resolve()?,
@@ -116,13 +107,13 @@ impl TunnelConfig {
         let public_url = optional_env("TUNNEL_URL")?
             .or_else(|| settings.tunnel.public_url.clone().filter(|s| !s.is_empty()));
 
-        if let Some(ref url) = public_url
-            && !url.starts_with("https://")
-        {
-            return Err(ConfigError::InvalidValue {
-                key: "TUNNEL_URL".to_string(),
-                message: "must start with https:// (webhooks require HTTPS)".to_string(),
-            });
+        if let Some(ref url) = public_url {
+            if !url.starts_with("https://") {
+                return Err(ConfigError::InvalidValue {
+                    key: "TUNNEL_URL".to_string(),
+                    message: "must start with https:// (webhooks require HTTPS)".to_string(),
+                });
+            }
         }
 
         Ok(Self { public_url })
@@ -153,15 +144,6 @@ pub enum DatabaseBackend {
     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;
 
@@ -197,7 +179,7 @@ pub struct DatabaseConfig {
 }
 
 impl DatabaseConfig {
-    fn resolve() -> Result<Self, ConfigError> {
+    fn resolve(bootstrap: &crate::bootstrap::BootstrapConfig) -> 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(),
@@ -209,8 +191,8 @@ impl DatabaseConfig {
 
         // 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(|| bootstrap.database_url.clone())
             .or_else(|| {
                 if backend == DatabaseBackend::LibSql {
                     Some("unused://libsql".to_string())
@@ -223,7 +205,15 @@ impl DatabaseConfig {
                 hint: "Run 'ironclaw onboard' or set DATABASE_URL environment variable".to_string(),
             })?;
 
-        let pool_size = parse_optional_env("DATABASE_POOL_SIZE", 10)?;
+        let pool_size = optional_env("DATABASE_POOL_SIZE")?
+            .map(|s| s.parse())
+            .transpose()
+            .map_err(|e| ConfigError::InvalidValue {
+                key: "DATABASE_POOL_SIZE".to_string(),
+                message: format!("must be a positive integer: {e}"),
+            })?
+            .or(bootstrap.database_pool_size)
+            .unwrap_or(10);
 
         let libsql_path = optional_env("LIBSQL_PATH")?.map(PathBuf::from).or_else(|| {
             if backend == DatabaseBackend::LibSql {
@@ -397,9 +387,6 @@ impl std::str::FromStr for NearAiApiMode {
 pub struct NearAiConfig {
     /// Model to use (e.g., "claude-3-5-sonnet-20241022", "gpt-4o")
     pub model: String,
-    /// Cheap/fast model for lightweight tasks (heartbeat, routing, evaluation).
-    /// Falls back to the main model if not set.
-    pub cheap_model: Option<String>,
     /// Base URL for the NEAR AI API (default: https://api.near.ai)
     pub base_url: String,
     /// Base URL for auth/refresh endpoints (default: https://private.near.ai)
@@ -410,44 +397,16 @@ pub struct NearAiConfig {
     pub api_mode: NearAiApiMode,
     /// API key for cloud-api (required for chat_completions mode)
     pub api_key: Option<SecretString>,
-    /// Optional fallback model for failover (default: None).
-    /// When set, a secondary provider is created with this model and wrapped
-    /// in a `FailoverProvider` so transient errors on the primary model
-    /// automatically fall through to the fallback.
-    pub fallback_model: Option<String>,
-    /// Maximum number of retries for transient errors (default: 3).
-    /// With the default of 3, the provider makes up to 4 total attempts
-    /// (1 initial + 3 retries) before giving up.
-    pub max_retries: u32,
-    /// Cooldown duration in seconds for the failover provider (default: 300).
-    /// When a provider accumulates enough consecutive failures it is skipped
-    /// for this many seconds.
-    pub failover_cooldown_secs: u64,
-    /// Number of consecutive retryable failures before a provider enters
-    /// cooldown (default: 3).
-    pub failover_cooldown_threshold: u32,
 }
 
 impl LlmConfig {
     fn resolve(settings: &Settings) -> Result<Self, ConfigError> {
-        // Determine backend: env var > settings > default (NearAi)
+        // Determine backend (default: NearAi)
         let backend: LlmBackend = if let Some(b) = optional_env("LLM_BACKEND")? {
             b.parse().map_err(|e| ConfigError::InvalidValue {
                 key: "LLM_BACKEND".to_string(),
                 message: e,
             })?
-        } else if let Some(ref b) = settings.llm_backend {
-            match b.parse() {
-                Ok(backend) => backend,
-                Err(e) => {
-                    tracing::warn!(
-                        "Invalid llm_backend '{}' in settings: {}. Using default NearAi.",
-                        b,
-                        e
-                    );
-                    LlmBackend::NearAi
-                }
-            }
         } else {
             LlmBackend::NearAi
         };
@@ -473,7 +432,6 @@ impl LlmConfig {
                     "fireworks::accounts/fireworks/models/llama4-maverick-instruct-basic"
                         .to_string()
                 }),
-            cheap_model: optional_env("NEARAI_CHEAP_MODEL")?,
             base_url: optional_env("NEARAI_BASE_URL")?
                 .unwrap_or_else(|| "https://cloud-api.near.ai".to_string()),
             auth_base_url: optional_env("NEARAI_AUTH_URL")?
@@ -483,10 +441,6 @@ impl LlmConfig {
                 .unwrap_or_else(default_session_path),
             api_mode,
             api_key: nearai_api_key,
-            fallback_model: optional_env("NEARAI_FALLBACK_MODEL")?,
-            max_retries: parse_optional_env("NEARAI_MAX_RETRIES", 3)?,
-            failover_cooldown_secs: parse_optional_env("LLM_FAILOVER_COOLDOWN_SECS", 300)?,
-            failover_cooldown_threshold: parse_optional_env("LLM_FAILOVER_THRESHOLD", 3)?,
         };
 
         // Resolve provider-specific configs based on backend
@@ -519,7 +473,6 @@ impl LlmConfig {
 
         let ollama = if backend == LlmBackend::Ollama {
             let base_url = optional_env("OLLAMA_BASE_URL")?
-                .or_else(|| settings.ollama_base_url.clone())
                 .unwrap_or_else(|| "http://localhost:11434".to_string());
             let model = optional_env("OLLAMA_MODEL")?.unwrap_or_else(|| "llama3".to_string());
             Some(OllamaConfig { base_url, model })
@@ -528,9 +481,8 @@ impl LlmConfig {
         };
 
         let openai_compatible = if backend == LlmBackend::OpenAiCompatible {
-            let base_url = optional_env("LLM_BASE_URL")?
-                .or_else(|| settings.openai_compatible_base_url.clone())
-                .ok_or_else(|| ConfigError::MissingRequired {
+            let base_url =
+                optional_env("LLM_BASE_URL")?.ok_or_else(|| ConfigError::MissingRequired {
                     key: "LLM_BASE_URL".to_string(),
                     hint: "Set LLM_BASE_URL when LLM_BACKEND=openai_compatible".to_string(),
                 })?;
@@ -900,41 +852,52 @@ impl std::fmt::Debug for SecretsConfig {
     }
 }
 
-/// Process-wide cache for the keychain master key.
-///
-/// Avoids re-prompting the OS keychain on every `SecretsConfig::resolve()` call
-/// (e.g. `Config::from_env()` then `Config::from_db()`). Thread-safe alternative
-/// to caching in a process env var.
 impl SecretsConfig {
-    /// Auto-detect secrets master key from env var, then OS keychain.
-    ///
-    /// Sequential probe: SECRETS_MASTER_KEY env var first, then OS keychain.
-    /// No saved "source" needed; just try each source in order.
-    async fn resolve() -> Result<Self, ConfigError> {
+    async fn resolve(bootstrap: &crate::bootstrap::BootstrapConfig) -> Result<Self, ConfigError> {
         use crate::settings::KeySource;
 
         let (master_key, source) = if let Some(env_key) = optional_env("SECRETS_MASTER_KEY")? {
             (Some(SecretString::from(env_key)), KeySource::Env)
         } else {
-            // Probe the OS keychain; if a key is stored, use it
-            match crate::secrets::keychain::get_master_key().await {
-                Ok(key_bytes) => {
-                    let key_hex: String = key_bytes.iter().map(|b| format!("{:02x}", b)).collect();
-                    (Some(SecretString::from(key_hex)), KeySource::Keychain)
+            match bootstrap.secrets_master_key_source {
+                KeySource::Keychain => {
+                    // Try to load from OS keychain (async on Linux)
+                    match crate::secrets::keychain::get_master_key().await {
+                        Ok(key_bytes) => {
+                            let key_hex: String =
+                                key_bytes.iter().map(|b| format!("{:02x}", b)).collect();
+                            (Some(SecretString::from(key_hex)), KeySource::Keychain)
+                        }
+                        Err(_) => {
+                            // Keychain configured but key not found
+                            // This might happen if keychain was cleared
+                            tracing::warn!(
+                                "Secrets configured for keychain but key not found. \
+                                 Run 'ironclaw onboard' to reconfigure."
+                            );
+                            (None, KeySource::None)
+                        }
+                    }
                 }
-                Err(_) => (None, KeySource::None),
+                KeySource::Env => {
+                    tracing::warn!(
+                        "Secrets configured for env var but SECRETS_MASTER_KEY not set."
+                    );
+                    (None, KeySource::None)
+                }
+                KeySource::None => (None, KeySource::None),
             }
         };
 
         let enabled = master_key.is_some();
 
-        if let Some(ref key) = master_key
-            && key.expose_secret().len() < 32
-        {
-            return Err(ConfigError::InvalidValue {
-                key: "SECRETS_MASTER_KEY".to_string(),
-                message: "must be at least 32 bytes for AES-256-GCM".to_string(),
-            });
+        if let Some(ref key) = master_key {
+            if key.expose_secret().len() < 32 {
+                return Err(ConfigError::InvalidValue {
+                    key: "SECRETS_MASTER_KEY".to_string(),
+                    message: "must be at least 32 bytes for AES-256-GCM".to_string(),
+                });
+            }
         }
 
         Ok(Self {
@@ -1388,64 +1351,17 @@ impl ClaudeCodeConfig {
     }
 }
 
-/// Load API keys from the encrypted secrets store into a thread-safe overlay.
-///
-/// This bridges the gap between secrets stored during onboarding and the
-/// env-var-first resolution in `LlmConfig::resolve()`. Keys in the overlay
-/// are read by `optional_env()` before falling back to `std::env::var()`,
-/// so explicit env vars always win.
-pub async fn inject_llm_keys_from_secrets(
-    secrets: &dyn crate::secrets::SecretsStore,
-    user_id: &str,
-) {
-    let mappings = [
-        ("llm_openai_api_key", "OPENAI_API_KEY"),
-        ("llm_anthropic_api_key", "ANTHROPIC_API_KEY"),
-        ("llm_compatible_api_key", "LLM_API_KEY"),
-    ];
-
-    let mut injected = HashMap::new();
-
-    for (secret_name, env_var) in mappings {
-        match std::env::var(env_var) {
-            Ok(val) if !val.is_empty() => continue,
-            _ => {}
-        }
-        match secrets.get_decrypted(user_id, secret_name).await {
-            Ok(decrypted) => {
-                injected.insert(env_var.to_string(), decrypted.expose().to_string());
-                tracing::debug!("Loaded secret '{}' for env var '{}'", secret_name, env_var);
-            }
-            Err(_) => {
-                // Secret doesn't exist, that's fine
-            }
-        }
-    }
-
-    let _ = INJECTED_VARS.set(injected);
-}
-
 // Helper functions
 
 fn optional_env(key: &str) -> Result<Option<String>, ConfigError> {
-    // Check real env vars first (always win over injected secrets)
     match std::env::var(key) {
-        Ok(val) if val.is_empty() => {}
-        Ok(val) => return Ok(Some(val)),
-        Err(std::env::VarError::NotPresent) => {}
-        Err(e) => {
-            return Err(ConfigError::ParseError(format!(
-                "failed to read {key}: {e}"
-            )));
-        }
+        Ok(val) if val.is_empty() => Ok(None),
+        Ok(val) => Ok(Some(val)),
+        Err(std::env::VarError::NotPresent) => Ok(None),
+        Err(e) => Err(ConfigError::ParseError(format!(
+            "failed to read {key}: {e}"
+        ))),
     }
-
-    // Fall back to thread-safe overlay (secrets injected from DB)
-    if let Some(val) = INJECTED_VARS.get().and_then(|map| map.get(key)) {
-        return Ok(Some(val.clone()));
-    }
-
-    Ok(None)
 }
 
 fn parse_optional_env<T>(key: &str, default: T) -> Result<T, ConfigError>

src/db/libsql_backend.rs

@@ -772,10 +772,10 @@ impl Database for LibSqlBackend {
             .await
             .map_err(|e| DatabaseError::Query(e.to_string()))?
         {
-            if let Ok(id_str) = row.get::<String>(0)
-                && let Ok(id) = id_str.parse()
-            {
-                ids.push(id);
+            if let Ok(id_str) = row.get::<String>(0) {
+                if let Ok(id) = id_str.parse() {
+                    ids.push(id);
+                }
             }
         }
         Ok(ids)
@@ -2199,10 +2199,10 @@ impl Database for LibSqlBackend {
                         e.content_preview = None;
                     }
                     // Update to latest timestamp
-                    if let (Some(existing), Some(new)) = (&e.updated_at, &updated_at)
-                        && new > existing
-                    {
-                        e.updated_at = Some(*new);
+                    if let (Some(existing), Some(new)) = (&e.updated_at, &updated_at) {
+                        if new > existing {
+                            e.updated_at = Some(*new);
+                        }
                     }
                 })
                 .or_insert(WorkspaceEntry {

src/error.rs

@@ -40,9 +40,6 @@ pub enum Error {
     #[error("Workspace error: {0}")]
     Workspace(#[from] WorkspaceError),
 
-    #[error("Hook error: {0}")]
-    Hook(#[from] crate::hooks::HookError),
-
     #[error("Orchestrator error: {0}")]
     Orchestrator(#[from] OrchestratorError),
 

src/estimation/cost.rs

@@ -20,6 +20,10 @@ impl CostEstimator {
 
         // Default tool costs (in USD or equivalent)
         tool_costs.insert("http".to_string(), dec!(0.0001)); // API call
+        tool_costs.insert("marketplace".to_string(), dec!(0.01)); // Gas costs
+        tool_costs.insert("ecommerce".to_string(), dec!(0.001)); // API call
+        tool_costs.insert("taskrabbit".to_string(), dec!(0.0)); // Cost comes from task itself
+        tool_costs.insert("restaurant".to_string(), dec!(0.001)); // API call
         tool_costs.insert("echo".to_string(), dec!(0.0)); // Free
         tool_costs.insert("time".to_string(), dec!(0.0)); // Free
         tool_costs.insert("json".to_string(), dec!(0.0)); // Free
@@ -70,7 +74,7 @@ mod tests {
         let estimator = CostEstimator::new();
 
         assert_eq!(estimator.estimate_tool("echo"), dec!(0.0));
-        assert_eq!(estimator.estimate_tool("http"), dec!(0.0001));
+        assert_eq!(estimator.estimate_tool("marketplace"), dec!(0.01));
         assert!(estimator.estimate_tool("unknown") > dec!(0.0));
     }
 

src/estimation/time.rs

@@ -16,6 +16,10 @@ impl TimeEstimator {
 
         // Default tool durations
         tool_durations.insert("http".to_string(), Duration::from_secs(5));
+        tool_durations.insert("marketplace".to_string(), Duration::from_secs(10));
+        tool_durations.insert("ecommerce".to_string(), Duration::from_secs(8));
+        tool_durations.insert("taskrabbit".to_string(), Duration::from_secs(30)); // Just API, not task itself
+        tool_durations.insert("restaurant".to_string(), Duration::from_secs(5));
         tool_durations.insert("echo".to_string(), Duration::from_millis(10));
         tool_durations.insert("time".to_string(), Duration::from_millis(1));
         tool_durations.insert("json".to_string(), Duration::from_millis(5));

src/evaluation/success.rs

@@ -144,11 +144,12 @@ impl SuccessEvaluator for RuleBasedEvaluator {
 
         // Check for critical errors
         for action in actions.iter().filter(|a| !a.success) {
-            if let Some(ref error) = action.error
-                && (error.to_lowercase().contains("critical")
-                    || error.to_lowercase().contains("fatal"))
-            {
-                issues.push(format!("Critical error in {}: {}", action.tool_name, error));
+            if let Some(ref error) = action.error {
+                if error.to_lowercase().contains("critical")
+                    || error.to_lowercase().contains("fatal")
+                {
+                    issues.push(format!("Critical error in {}: {}", action.tool_name, error));
+                }
             }
         }
 

src/extensions/manager.rs

@@ -492,13 +492,13 @@ impl ExtensionManager {
         }
 
         // Check Content-Length header before downloading the full body
-        if let Some(len) = response.content_length()
-            && len as usize > MAX_WASM_SIZE
-        {
-            return Err(ExtensionError::InstallFailed(format!(
-                "WASM binary too large ({} bytes, max {} bytes)",
-                len, MAX_WASM_SIZE
-            )));
+        if let Some(len) = response.content_length() {
+            if len as usize > MAX_WASM_SIZE {
+                return Err(ExtensionError::InstallFailed(format!(
+                    "WASM binary too large ({} bytes, max {} bytes)",
+                    len, MAX_WASM_SIZE
+                )));
+            }
         }
 
         let bytes = response
@@ -768,27 +768,27 @@ impl ExtensionManager {
         };
 
         // Check env var first
-        if let Some(ref env_var) = auth.env_var
-            && let Ok(value) = std::env::var(env_var)
-        {
-            // Store the env var value as a secret
-            let params =
-                CreateSecretParams::new(&auth.secret_name, &value).with_provider(name.to_string());
-            self.secrets
-                .create(&self.user_id, params)
-                .await
-                .map_err(|e| ExtensionError::AuthFailed(e.to_string()))?;
+        if let Some(ref env_var) = auth.env_var {
+            if let Ok(value) = std::env::var(env_var) {
+                // Store the env var value as a secret
+                let params = CreateSecretParams::new(&auth.secret_name, &value)
+                    .with_provider(name.to_string());
+                self.secrets
+                    .create(&self.user_id, params)
+                    .await
+                    .map_err(|e| ExtensionError::AuthFailed(e.to_string()))?;
 
-            return Ok(AuthResult {
-                name: name.to_string(),
-                kind: ExtensionKind::WasmTool,
-                auth_url: None,
-                callback_type: None,
-                instructions: None,
-                setup_url: None,
-                awaiting_token: false,
-                status: "authenticated".to_string(),
-            });
+                return Ok(AuthResult {
+                    name: name.to_string(),
+                    kind: ExtensionKind::WasmTool,
+                    auth_url: None,
+                    callback_type: None,
+                    instructions: None,
+                    setup_url: None,
+                    awaiting_token: false,
+                    status: "authenticated".to_string(),
+                });
+            }
         }
 
         // Check if already authenticated

src/history/store.rs

@@ -36,11 +36,6 @@ pub struct Store {
 
 #[cfg(feature = "postgres")]
 impl Store {
-    /// Wrap an existing pool (useful when the caller already has a connection).
-    pub fn from_pool(pool: Pool) -> Self {
-        Self { pool }
-    }
-
     /// Create a new store and connect to the database.
     pub async fn new(config: &DatabaseConfig) -> Result<Self, DatabaseError> {
         let mut cfg = Config::new();

src/hooks/hook.rs

@@ -1,199 +0,0 @@
-//! Core hook types and traits.
-
-use std::time::Duration;
-
-use async_trait::async_trait;
-
-/// Points in the agent lifecycle where hooks can be attached.
-#[derive(Debug, Clone, Copy, PartialEq, Eq, Hash)]
-pub enum HookPoint {
-    /// Before processing an inbound user message.
-    BeforeInbound,
-    /// Before executing a tool call.
-    BeforeToolCall,
-    /// Before sending an outbound response.
-    BeforeOutbound,
-    /// When a new session starts.
-    OnSessionStart,
-    /// When a session ends (pruned or expired).
-    OnSessionEnd,
-    /// Transform the final response before completing a turn.
-    TransformResponse,
-}
-
-/// Contextual data carried with each hook invocation.
-#[derive(Debug, Clone)]
-pub enum HookEvent {
-    /// An inbound user message about to be processed.
-    Inbound {
-        user_id: String,
-        channel: String,
-        content: String,
-        thread_id: Option<String>,
-    },
-    /// A tool call about to be executed.
-    ToolCall {
-        tool_name: String,
-        parameters: serde_json::Value,
-        user_id: String,
-        /// "chat" for interactive, or a job ID string for autonomous jobs.
-        context: String,
-    },
-    /// An outbound response about to be sent.
-    Outbound {
-        user_id: String,
-        channel: String,
-        content: String,
-        thread_id: Option<String>,
-    },
-    /// A new session was created.
-    SessionStart { user_id: String, session_id: String },
-    /// A session was ended (pruned).
-    SessionEnd { user_id: String, session_id: String },
-    /// The final response is being transformed before completing a turn.
-    ResponseTransform {
-        user_id: String,
-        thread_id: String,
-        response: String,
-    },
-}
-
-impl HookEvent {
-    /// Returns the [`HookPoint`] this event corresponds to.
-    pub fn hook_point(&self) -> HookPoint {
-        match self {
-            HookEvent::Inbound { .. } => HookPoint::BeforeInbound,
-            HookEvent::ToolCall { .. } => HookPoint::BeforeToolCall,
-            HookEvent::Outbound { .. } => HookPoint::BeforeOutbound,
-            HookEvent::SessionStart { .. } => HookPoint::OnSessionStart,
-            HookEvent::SessionEnd { .. } => HookPoint::OnSessionEnd,
-            HookEvent::ResponseTransform { .. } => HookPoint::TransformResponse,
-        }
-    }
-
-    /// Apply a modification string to the event's primary content field.
-    pub fn apply_modification(&mut self, modified: &str) {
-        match self {
-            HookEvent::Inbound { content, .. } | HookEvent::Outbound { content, .. } => {
-                *content = modified.to_string();
-            }
-            HookEvent::ToolCall { parameters, .. } => match serde_json::from_str(modified) {
-                Ok(parsed) => *parameters = parsed,
-                Err(e) => {
-                    tracing::warn!(
-                        "Hook returned non-JSON modification for ToolCall, ignoring: {}",
-                        e
-                    );
-                }
-            },
-            HookEvent::ResponseTransform { response, .. } => {
-                *response = modified.to_string();
-            }
-            HookEvent::SessionStart { .. } | HookEvent::SessionEnd { .. } => {
-                // Session events don't have modifiable content
-            }
-        }
-    }
-}
-
-/// The result of executing a hook.
-#[derive(Debug, Clone)]
-pub enum HookOutcome {
-    /// Continue processing, optionally with modified content.
-    Continue {
-        /// If `Some`, replace the event's primary content with this value.
-        modified: Option<String>,
-    },
-    /// Reject the event entirely.
-    Reject {
-        /// Human-readable reason for the rejection.
-        reason: String,
-    },
-}
-
-impl HookOutcome {
-    /// Shorthand for `Continue { modified: None }`.
-    pub fn ok() -> Self {
-        HookOutcome::Continue { modified: None }
-    }
-
-    /// Shorthand for `Continue { modified: Some(value) }`.
-    pub fn modify(value: String) -> Self {
-        HookOutcome::Continue {
-            modified: Some(value),
-        }
-    }
-
-    /// Shorthand for `Reject { reason }`.
-    pub fn reject(reason: impl Into<String>) -> Self {
-        HookOutcome::Reject {
-            reason: reason.into(),
-        }
-    }
-}
-
-/// How to handle hook execution failures.
-#[derive(Debug, Clone, Copy, PartialEq, Eq)]
-pub enum HookFailureMode {
-    /// On error/timeout, continue processing as if the hook returned `ok()`.
-    FailOpen,
-    /// On error/timeout, reject the event.
-    FailClosed,
-}
-
-/// Hook execution errors.
-#[derive(Debug, thiserror::Error)]
-pub enum HookError {
-    #[error("Hook execution failed: {reason}")]
-    ExecutionFailed { reason: String },
-
-    #[error("Hook timed out after {timeout:?}")]
-    Timeout { timeout: Duration },
-
-    #[error("Hook rejected: {reason}")]
-    Rejected { reason: String },
-}
-
-/// Context passed to hooks alongside the event.
-pub struct HookContext {
-    /// Arbitrary metadata hooks can use.
-    pub metadata: serde_json::Value,
-}
-
-impl Default for HookContext {
-    fn default() -> Self {
-        Self {
-            metadata: serde_json::Value::Null,
-        }
-    }
-}
-
-/// Trait for implementing lifecycle hooks.
-///
-/// Hooks intercept and can modify agent operations at well-defined points.
-#[async_trait]
-pub trait Hook: Send + Sync {
-    /// A unique name for this hook.
-    fn name(&self) -> &str;
-
-    /// The lifecycle points this hook should be called at.
-    fn hook_points(&self) -> &[HookPoint];
-
-    /// How to handle failures in this hook.
-    ///
-    /// Default: `FailOpen` (continue on error).
-    fn failure_mode(&self) -> HookFailureMode {
-        HookFailureMode::FailOpen
-    }
-
-    /// Maximum time this hook is allowed to run.
-    ///
-    /// Default: 5 seconds.
-    fn timeout(&self) -> Duration {
-        Duration::from_secs(5)
-    }
-
-    /// Execute the hook.
-    async fn execute(&self, event: &HookEvent, ctx: &HookContext)
-    -> Result<HookOutcome, HookError>;
-}

src/hooks/mod.rs

@@ -1,19 +0,0 @@
-//! Lifecycle hooks for intercepting and transforming agent operations.
-//!
-//! The hook system provides 6 well-defined interception points:
-//!
-//! - **BeforeInbound** — Before processing an inbound user message
-//! - **BeforeToolCall** — Before executing a tool call
-//! - **BeforeOutbound** — Before sending an outbound response
-//! - **OnSessionStart** — When a new session starts
-//! - **OnSessionEnd** — When a session ends
-//! - **TransformResponse** — Transform the final response before completing a turn
-//!
-//! Hooks are executed in priority order (lower number = higher priority).
-//! Each hook can pass through, modify content, or reject the event.
-
-pub mod hook;
-pub mod registry;
-
-pub use hook::{Hook, HookContext, HookError, HookEvent, HookFailureMode, HookOutcome, HookPoint};
-pub use registry::HookRegistry;

src/hooks/registry.rs

@@ -1,555 +0,0 @@
-//! Hook registry for managing and executing lifecycle hooks.
-
-use std::sync::Arc;
-
-use tokio::sync::RwLock;
-
-use crate::hooks::hook::{Hook, HookContext, HookError, HookEvent, HookFailureMode, HookOutcome};
-
-/// A registered hook with its priority.
-struct HookEntry {
-    hook: Arc<dyn Hook>,
-    priority: u32,
-}
-
-/// Registry that manages hooks and executes them at lifecycle points.
-///
-/// Hooks are executed in priority order (lower number = higher priority).
-/// A `Reject` outcome stops the chain immediately.
-/// A `Modify` outcome chains through subsequent hooks.
-pub struct HookRegistry {
-    hooks: RwLock<Vec<HookEntry>>,
-}
-
-impl HookRegistry {
-    /// Create an empty registry.
-    pub fn new() -> Self {
-        Self {
-            hooks: RwLock::new(Vec::new()),
-        }
-    }
-
-    /// Register a hook with default priority (100).
-    pub async fn register(&self, hook: Arc<dyn Hook>) {
-        self.register_with_priority(hook, 100).await;
-    }
-
-    /// Register a hook with a specific priority.
-    ///
-    /// Lower priority number = runs first.
-    pub async fn register_with_priority(&self, hook: Arc<dyn Hook>, priority: u32) {
-        let mut hooks = self.hooks.write().await;
-        hooks.push(HookEntry { hook, priority });
-        hooks.sort_by_key(|e| e.priority);
-    }
-
-    /// Unregister a hook by name. Returns `true` if it was found and removed.
-    pub async fn unregister(&self, name: &str) -> bool {
-        let mut hooks = self.hooks.write().await;
-        let before = hooks.len();
-        hooks.retain(|e| e.hook.name() != name);
-        hooks.len() < before
-    }
-
-    /// List all registered hook names (in priority order).
-    pub async fn list(&self) -> Vec<String> {
-        let hooks = self.hooks.read().await;
-        hooks.iter().map(|e| e.hook.name().to_string()).collect()
-    }
-
-    /// Run all hooks matching the event's hook point.
-    ///
-    /// - Hooks run in priority order (lowest first).
-    /// - `Reject` stops the chain immediately.
-    /// - `Modify` chains the modification through subsequent hooks.
-    /// - Timeout/error handling respects each hook's `failure_mode`.
-    pub async fn run(&self, event: &HookEvent) -> Result<HookOutcome, HookError> {
-        let point = event.hook_point();
-        let ctx = HookContext::default();
-
-        // Clone matching hooks and drop the read guard before executing.
-        // Each hook can run up to its timeout, so holding the guard would
-        // block concurrent register/unregister/run calls.
-        let matching: Vec<Arc<dyn Hook>> = {
-            let hooks = self.hooks.read().await;
-            hooks
-                .iter()
-                .filter(|e| e.hook.hook_points().contains(&point))
-                .map(|e| e.hook.clone())
-                .collect()
-        };
-
-        if matching.is_empty() {
-            return Ok(HookOutcome::ok());
-        }
-
-        let mut current_event = event.clone();
-
-        for hook in &matching {
-            let timeout = hook.timeout();
-
-            let result = tokio::time::timeout(timeout, hook.execute(&current_event, &ctx)).await;
-
-            match result {
-                Ok(Ok(HookOutcome::Reject { reason })) => {
-                    tracing::debug!(hook = hook.name(), "Hook rejected: {}", reason);
-                    return Err(HookError::Rejected { reason });
-                }
-                Ok(Ok(HookOutcome::Continue {
-                    modified: Some(value),
-                })) => {
-                    tracing::debug!(hook = hook.name(), "Hook modified content");
-                    current_event.apply_modification(&value);
-                }
-                Ok(Ok(HookOutcome::Continue { modified: None })) => {
-                    // No-op, continue chain
-                }
-                Ok(Err(err)) => match hook.failure_mode() {
-                    HookFailureMode::FailOpen => {
-                        tracing::warn!(hook = hook.name(), "Hook failed (fail-open): {}", err);
-                    }
-                    HookFailureMode::FailClosed => {
-                        tracing::warn!(hook = hook.name(), "Hook failed (fail-closed): {}", err);
-                        return Err(HookError::ExecutionFailed {
-                            reason: format!("Hook '{}' failed: {}", hook.name(), err),
-                        });
-                    }
-                },
-                Err(_elapsed) => match hook.failure_mode() {
-                    HookFailureMode::FailOpen => {
-                        tracing::warn!(
-                            hook = hook.name(),
-                            "Hook timed out (fail-open) after {:?}",
-                            timeout
-                        );
-                    }
-                    HookFailureMode::FailClosed => {
-                        tracing::warn!(
-                            hook = hook.name(),
-                            "Hook timed out (fail-closed) after {:?}",
-                            timeout
-                        );
-                        return Err(HookError::Timeout { timeout });
-                    }
-                },
-            }
-        }
-
-        // Determine final outcome by comparing with original event
-        let modified = extract_content(&current_event);
-        let original = extract_content(event);
-
-        if modified != original {
-            Ok(HookOutcome::modify(modified))
-        } else {
-            Ok(HookOutcome::ok())
-        }
-    }
-}
-
-impl Default for HookRegistry {
-    fn default() -> Self {
-        Self::new()
-    }
-}
-
-/// Extract the primary content string from a hook event.
-fn extract_content(event: &HookEvent) -> String {
-    match event {
-        HookEvent::Inbound { content, .. } | HookEvent::Outbound { content, .. } => content.clone(),
-        HookEvent::ToolCall { parameters, .. } => {
-            serde_json::to_string(parameters).unwrap_or_default()
-        }
-        HookEvent::ResponseTransform { response, .. } => response.clone(),
-        HookEvent::SessionStart { session_id, .. } | HookEvent::SessionEnd { session_id, .. } => {
-            session_id.clone()
-        }
-    }
-}
-
-#[cfg(test)]
-mod tests {
-    use super::*;
-    use crate::hooks::hook::{HookFailureMode, HookPoint};
-    use async_trait::async_trait;
-    use std::time::Duration;
-
-    /// A test hook that always returns ok.
-    struct PassthroughHook {
-        name: String,
-        points: Vec<HookPoint>,
-    }
-
-    #[async_trait]
-    impl Hook for PassthroughHook {
-        fn name(&self) -> &str {
-            &self.name
-        }
-        fn hook_points(&self) -> &[HookPoint] {
-            &self.points
-        }
-        async fn execute(
-            &self,
-            _event: &HookEvent,
-            _ctx: &HookContext,
-        ) -> Result<HookOutcome, HookError> {
-            Ok(HookOutcome::ok())
-        }
-    }
-
-    /// A hook that modifies content by appending a suffix.
-    struct ModifyHook {
-        name: String,
-        suffix: String,
-        points: Vec<HookPoint>,
-    }
-
-    #[async_trait]
-    impl Hook for ModifyHook {
-        fn name(&self) -> &str {
-            &self.name
-        }
-        fn hook_points(&self) -> &[HookPoint] {
-            &self.points
-        }
-        async fn execute(
-            &self,
-            event: &HookEvent,
-            _ctx: &HookContext,
-        ) -> Result<HookOutcome, HookError> {
-            let content = extract_content(event);
-            Ok(HookOutcome::modify(format!("{}{}", content, self.suffix)))
-        }
-    }
-
-    /// A hook that always rejects.
-    struct RejectHook {
-        name: String,
-        reason: String,
-        points: Vec<HookPoint>,
-    }
-
-    #[async_trait]
-    impl Hook for RejectHook {
-        fn name(&self) -> &str {
-            &self.name
-        }
-        fn hook_points(&self) -> &[HookPoint] {
-            &self.points
-        }
-        async fn execute(
-            &self,
-            _event: &HookEvent,
-            _ctx: &HookContext,
-        ) -> Result<HookOutcome, HookError> {
-            Ok(HookOutcome::reject(&self.reason))
-        }
-    }
-
-    /// A hook that always errors.
-    struct ErrorHook {
-        name: String,
-        points: Vec<HookPoint>,
-        failure_mode: HookFailureMode,
-    }
-
-    #[async_trait]
-    impl Hook for ErrorHook {
-        fn name(&self) -> &str {
-            &self.name
-        }
-        fn hook_points(&self) -> &[HookPoint] {
-            &self.points
-        }
-        fn failure_mode(&self) -> HookFailureMode {
-            self.failure_mode
-        }
-        async fn execute(
-            &self,
-            _event: &HookEvent,
-            _ctx: &HookContext,
-        ) -> Result<HookOutcome, HookError> {
-            Err(HookError::ExecutionFailed {
-                reason: "test error".into(),
-            })
-        }
-    }
-
-    /// A hook that sleeps longer than its timeout.
-    struct SlowHook {
-        name: String,
-        points: Vec<HookPoint>,
-        failure_mode: HookFailureMode,
-    }
-
-    #[async_trait]
-    impl Hook for SlowHook {
-        fn name(&self) -> &str {
-            &self.name
-        }
-        fn hook_points(&self) -> &[HookPoint] {
-            &self.points
-        }
-        fn failure_mode(&self) -> HookFailureMode {
-            self.failure_mode
-        }
-        fn timeout(&self) -> Duration {
-            Duration::from_millis(50)
-        }
-        async fn execute(
-            &self,
-            _event: &HookEvent,
-            _ctx: &HookContext,
-        ) -> Result<HookOutcome, HookError> {
-            tokio::time::sleep(Duration::from_millis(200)).await;
-            Ok(HookOutcome::ok())
-        }
-    }
-
-    fn test_event() -> HookEvent {
-        HookEvent::Inbound {
-            user_id: "user-1".into(),
-            channel: "test".into(),
-            content: "hello".into(),
-            thread_id: None,
-        }
-    }
-
-    #[tokio::test]
-    async fn test_empty_registry_returns_ok() {
-        let registry = HookRegistry::new();
-        let result = registry.run(&test_event()).await;
-        assert!(result.is_ok());
-        assert!(matches!(
-            result.unwrap(),
-            HookOutcome::Continue { modified: None }
-        ));
-    }
-
-    #[tokio::test]
-    async fn test_register_and_list() {
-        let registry = HookRegistry::new();
-        registry
-            .register(Arc::new(PassthroughHook {
-                name: "hook-a".into(),
-                points: vec![HookPoint::BeforeInbound],
-            }))
-            .await;
-        registry
-            .register(Arc::new(PassthroughHook {
-                name: "hook-b".into(),
-                points: vec![HookPoint::BeforeInbound],
-            }))
-            .await;
-
-        let names = registry.list().await;
-        assert_eq!(names, vec!["hook-a", "hook-b"]);
-    }
-
-    #[tokio::test]
-    async fn test_priority_ordering() {
-        let registry = HookRegistry::new();
-
-        // Register in reverse priority order
-        registry
-            .register_with_priority(
-                Arc::new(ModifyHook {
-                    name: "low-prio".into(),
-                    suffix: "-LOW".into(),
-                    points: vec![HookPoint::BeforeInbound],
-                }),
-                200,
-            )
-            .await;
-        registry
-            .register_with_priority(
-                Arc::new(ModifyHook {
-                    name: "high-prio".into(),
-                    suffix: "-HIGH".into(),
-                    points: vec![HookPoint::BeforeInbound],
-                }),
-                10,
-            )
-            .await;
-
-        // Should run in priority order: high-prio first, then low-prio
-        let names = registry.list().await;
-        assert_eq!(names[0], "high-prio");
-        assert_eq!(names[1], "low-prio");
-
-        let result = registry.run(&test_event()).await.unwrap();
-        match result {
-            HookOutcome::Continue { modified: Some(m) } => {
-                // "hello" -> "hello-HIGH" -> "hello-HIGH-LOW"
-                assert_eq!(m, "hello-HIGH-LOW");
-            }
-            other => panic!("Expected modification chain, got: {:?}", other),
-        }
-    }
-
-    #[tokio::test]
-    async fn test_reject_stops_chain() {
-        let registry = HookRegistry::new();
-
-        registry
-            .register_with_priority(
-                Arc::new(RejectHook {
-                    name: "blocker".into(),
-                    reason: "blocked".into(),
-                    points: vec![HookPoint::BeforeInbound],
-                }),
-                10,
-            )
-            .await;
-        registry
-            .register_with_priority(
-                Arc::new(ModifyHook {
-                    name: "modifier".into(),
-                    suffix: "-MODIFIED".into(),
-                    points: vec![HookPoint::BeforeInbound],
-                }),
-                20,
-            )
-            .await;
-
-        let result = registry.run(&test_event()).await;
-        assert!(result.is_err());
-        match result.unwrap_err() {
-            HookError::Rejected { reason } => assert_eq!(reason, "blocked"),
-            other => panic!("Expected Rejected, got: {:?}", other),
-        }
-    }
-
-    #[tokio::test]
-    async fn test_modification_chaining() {
-        let registry = HookRegistry::new();
-
-        registry
-            .register_with_priority(
-                Arc::new(ModifyHook {
-                    name: "first".into(),
-                    suffix: "-A".into(),
-                    points: vec![HookPoint::BeforeInbound],
-                }),
-                10,
-            )
-            .await;
-        registry
-            .register_with_priority(
-                Arc::new(ModifyHook {
-                    name: "second".into(),
-                    suffix: "-B".into(),
-                    points: vec![HookPoint::BeforeInbound],
-                }),
-                20,
-            )
-            .await;
-
-        let result = registry.run(&test_event()).await.unwrap();
-        match result {
-            HookOutcome::Continue { modified: Some(m) } => {
-                assert_eq!(m, "hello-A-B");
-            }
-            other => panic!("Expected chained modification, got: {:?}", other),
-        }
-    }
-
-    #[tokio::test]
-    async fn test_fail_open_on_error() {
-        let registry = HookRegistry::new();
-        registry
-            .register(Arc::new(ErrorHook {
-                name: "err-open".into(),
-                points: vec![HookPoint::BeforeInbound],
-                failure_mode: HookFailureMode::FailOpen,
-            }))
-            .await;
-
-        let result = registry.run(&test_event()).await;
-        assert!(result.is_ok());
-    }
-
-    #[tokio::test]
-    async fn test_fail_closed_on_error() {
-        let registry = HookRegistry::new();
-        registry
-            .register(Arc::new(ErrorHook {
-                name: "err-closed".into(),
-                points: vec![HookPoint::BeforeInbound],
-                failure_mode: HookFailureMode::FailClosed,
-            }))
-            .await;
-
-        let result = registry.run(&test_event()).await;
-        assert!(result.is_err());
-        assert!(matches!(
-            result.unwrap_err(),
-            HookError::ExecutionFailed { .. }
-        ));
-    }
-
-    #[tokio::test]
-    async fn test_fail_open_on_timeout() {
-        let registry = HookRegistry::new();
-        registry
-            .register(Arc::new(SlowHook {
-                name: "slow-open".into(),
-                points: vec![HookPoint::BeforeInbound],
-                failure_mode: HookFailureMode::FailOpen,
-            }))
-            .await;
-
-        let result = registry.run(&test_event()).await;
-        assert!(result.is_ok());
-    }
-
-    #[tokio::test]
-    async fn test_fail_closed_on_timeout() {
-        let registry = HookRegistry::new();
-        registry
-            .register(Arc::new(SlowHook {
-                name: "slow-closed".into(),
-                points: vec![HookPoint::BeforeInbound],
-                failure_mode: HookFailureMode::FailClosed,
-            }))
-            .await;
-
-        let result = registry.run(&test_event()).await;
-        assert!(result.is_err());
-        assert!(matches!(result.unwrap_err(), HookError::Timeout { .. }));
-    }
-
-    #[tokio::test]
-    async fn test_unregister() {
-        let registry = HookRegistry::new();
-        registry
-            .register(Arc::new(PassthroughHook {
-                name: "removable".into(),
-                points: vec![HookPoint::BeforeInbound],
-            }))
-            .await;
-
-        assert_eq!(registry.list().await.len(), 1);
-        assert!(registry.unregister("removable").await);
-        assert_eq!(registry.list().await.len(), 0);
-
-        // Unregistering non-existent returns false
-        assert!(!registry.unregister("nonexistent").await);
-    }
-
-    #[tokio::test]
-    async fn test_hooks_only_match_their_points() {
-        let registry = HookRegistry::new();
-        registry
-            .register(Arc::new(RejectHook {
-                name: "outbound-only".into(),
-                reason: "blocked".into(),
-                points: vec![HookPoint::BeforeOutbound],
-            }))
-            .await;
-
-        // Inbound event should not be affected by outbound-only hook
-        let result = registry.run(&test_event()).await;
-        assert!(result.is_ok());
-    }
-}

src/lib.rs

@@ -39,7 +39,6 @@
 //! - **Continuous learning** - Improve estimates from historical data
 
 pub mod agent;
-pub mod boot_screen;
 pub mod bootstrap;
 pub mod channels;
 pub mod cli;
@@ -51,7 +50,6 @@ pub mod estimation;
 pub mod evaluation;
 pub mod extensions;
 pub mod history;
-pub mod hooks;
 pub mod llm;
 pub mod orchestrator;
 pub mod pairing;
@@ -61,7 +59,6 @@ pub mod secrets;
 pub mod settings;
 pub mod setup;
 pub mod tools;
-pub mod tracing_fmt;
 pub mod util;
 pub mod worker;
 pub mod workspace;

src/llm/mod.rs

@@ -8,16 +8,13 @@
 //! - **OpenAI-compatible**: Any endpoint that speaks the OpenAI API
 
 mod costs;
-pub mod failover;
 mod nearai;
 mod nearai_chat;
 mod provider;
 mod reasoning;
-mod retry;
 mod rig_adapter;
 pub mod session;
 
-pub use failover::{CooldownConfig, FailoverProvider};
 pub use nearai::{ModelInfo, NearAiProvider};
 pub use nearai_chat::NearAiChatProvider;
 pub use provider::{
@@ -36,7 +33,7 @@ use std::sync::Arc;
 use rig::client::CompletionClient;
 use secrecy::ExposeSecret;
 
-use crate::config::{LlmBackend, LlmConfig, NearAiApiMode, NearAiConfig};
+use crate::config::{LlmBackend, LlmConfig, NearAiApiMode};
 use crate::error::LlmError;
 
 /// Create an LLM provider based on configuration.
@@ -49,7 +46,7 @@ pub fn create_llm_provider(
     session: Arc<SessionManager>,
 ) -> Result<Arc<dyn LlmProvider>, LlmError> {
     match config.backend {
-        LlmBackend::NearAi => create_llm_provider_with_config(&config.nearai, session),
+        LlmBackend::NearAi => create_nearai_provider(config, session),
         LlmBackend::OpenAi => create_openai_provider(config),
         LlmBackend::Anthropic => create_anthropic_provider(config),
         LlmBackend::Ollama => create_ollama_provider(config),
@@ -57,28 +54,21 @@ pub fn create_llm_provider(
     }
 }
 
-/// Create an LLM provider from a `NearAiConfig` directly.
-///
-/// This is useful when constructing additional providers for failover,
-/// where only the model name differs from the primary config.
-pub fn create_llm_provider_with_config(
-    config: &NearAiConfig,
+fn create_nearai_provider(
+    config: &LlmConfig,
     session: Arc<SessionManager>,
 ) -> Result<Arc<dyn LlmProvider>, LlmError> {
-    match config.api_mode {
+    match config.nearai.api_mode {
         NearAiApiMode::Responses => {
-            tracing::info!(
-                model = %config.model,
-                "Using Responses API (chat-api) with session auth"
-            );
-            Ok(Arc::new(NearAiProvider::new(config.clone(), session)))
+            tracing::info!("Using NEAR AI Responses API (chat-api) with session auth");
+            Ok(Arc::new(NearAiProvider::new(
+                config.nearai.clone(),
+                session,
+            )))
         }
         NearAiApiMode::ChatCompletions => {
-            tracing::info!(
-                model = %config.model,
-                "Using Chat Completions API (cloud-api) with API key auth"
-            );
-            Ok(Arc::new(NearAiChatProvider::new(config.clone())?))
+            tracing::info!("Using NEAR AI Chat Completions API (cloud-api) with API key auth");
+            Ok(Arc::new(NearAiChatProvider::new(config.nearai.clone())?))
         }
     }
 }
@@ -183,108 +173,3 @@ fn create_openai_compatible_provider(config: &LlmConfig) -> Result<Arc<dyn LlmPr
     );
     Ok(Arc::new(RigAdapter::new(model, &compat.model)))
 }
-
-/// Create a cheap/fast LLM provider for lightweight tasks (heartbeat, routing, evaluation).
-///
-/// Uses `NEARAI_CHEAP_MODEL` if set, otherwise falls back to the main provider.
-/// Currently only supports NEAR AI backends (Responses and ChatCompletions modes).
-pub fn create_cheap_llm_provider(
-    config: &LlmConfig,
-    session: Arc<SessionManager>,
-) -> Result<Option<Arc<dyn LlmProvider>>, LlmError> {
-    let Some(ref cheap_model) = config.nearai.cheap_model else {
-        return Ok(None);
-    };
-
-    if config.backend != LlmBackend::NearAi {
-        tracing::warn!(
-            "NEARAI_CHEAP_MODEL is set but LLM_BACKEND is {:?}, not NearAi. \
-             Cheap model setting will be ignored.",
-            config.backend
-        );
-        return Ok(None);
-    }
-
-    let mut cheap_config = config.nearai.clone();
-    cheap_config.model = cheap_model.clone();
-
-    tracing::info!("Cheap LLM provider: {}", cheap_model);
-
-    match cheap_config.api_mode {
-        NearAiApiMode::Responses => Ok(Some(Arc::new(NearAiProvider::new(cheap_config, session)))),
-        NearAiApiMode::ChatCompletions => {
-            Ok(Some(Arc::new(NearAiChatProvider::new(cheap_config)?)))
-        }
-    }
-}
-
-#[cfg(test)]
-mod tests {
-    use super::*;
-    use crate::config::{LlmBackend, NearAiApiMode, NearAiConfig};
-    use std::path::PathBuf;
-
-    fn test_nearai_config() -> NearAiConfig {
-        NearAiConfig {
-            model: "test-model".to_string(),
-            cheap_model: None,
-            base_url: "https://api.near.ai".to_string(),
-            auth_base_url: "https://private.near.ai".to_string(),
-            session_path: PathBuf::from("/tmp/test-session.json"),
-            api_mode: NearAiApiMode::Responses,
-            api_key: None,
-            fallback_model: None,
-            max_retries: 3,
-            failover_cooldown_secs: 300,
-            failover_cooldown_threshold: 3,
-        }
-    }
-
-    fn test_llm_config() -> LlmConfig {
-        LlmConfig {
-            backend: LlmBackend::NearAi,
-            nearai: test_nearai_config(),
-            openai: None,
-            anthropic: None,
-            ollama: None,
-            openai_compatible: None,
-        }
-    }
-
-    #[test]
-    fn test_create_cheap_llm_provider_returns_none_when_not_configured() {
-        let config = test_llm_config();
-        let session = Arc::new(SessionManager::new(SessionConfig::default()));
-
-        let result = create_cheap_llm_provider(&config, session);
-        assert!(result.is_ok());
-        assert!(result.unwrap().is_none());
-    }
-
-    #[test]
-    fn test_create_cheap_llm_provider_creates_provider_when_configured() {
-        let mut config = test_llm_config();
-        config.nearai.cheap_model = Some("cheap-test-model".to_string());
-
-        let session = Arc::new(SessionManager::new(SessionConfig::default()));
-        let result = create_cheap_llm_provider(&config, session);
-
-        assert!(result.is_ok());
-        let provider = result.unwrap();
-        assert!(provider.is_some());
-        assert_eq!(provider.unwrap().model_name(), "cheap-test-model");
-    }
-
-    #[test]
-    fn test_create_cheap_llm_provider_ignored_for_non_nearai_backend() {
-        let mut config = test_llm_config();
-        config.backend = LlmBackend::OpenAi;
-        config.nearai.cheap_model = Some("cheap-test-model".to_string());
-
-        let session = Arc::new(SessionManager::new(SessionConfig::default()));
-        let result = create_cheap_llm_provider(&config, session);
-
-        assert!(result.is_ok());
-        assert!(result.unwrap().is_none());
-    }
-}

src/llm/nearai.rs

@@ -19,7 +19,6 @@ use crate::llm::provider::{
     ChatMessage, CompletionRequest, CompletionResponse, FinishReason, LlmProvider, Role, ToolCall,
     ToolCompletionRequest, ToolCompletionResponse,
 };
-use crate::llm::retry::{is_retryable_status, retry_backoff_delay};
 use crate::llm::session::SessionManager;
 
 /// Information about an available model from NEAR AI API.
@@ -210,20 +209,20 @@ impl NearAiProvider {
             data: Option<Vec<ModelEntry>>,
         }
 
-        if let Ok(resp) = serde_json::from_str::<ModelsResponse>(&response_text)
-            && let Some(entries) = resp.models.or(resp.data)
-        {
-            let models: Vec<ModelInfo> = entries
-                .into_iter()
-                .filter_map(|e| {
-                    e.get_name().map(|name| ModelInfo {
-                        name,
-                        provider: None,
+        if let Ok(resp) = serde_json::from_str::<ModelsResponse>(&response_text) {
+            if let Some(entries) = resp.models.or(resp.data) {
+                let models: Vec<ModelInfo> = entries
+                    .into_iter()
+                    .filter_map(|e| {
+                        e.get_name().map(|name| ModelInfo {
+                            name,
+                            provider: None,
+                        })
                     })
-                })
-                .collect();
-            if !models.is_empty() {
-                return Ok(models);
+                    .collect();
+                if !models.is_empty() {
+                    return Ok(models);
+                }
             }
         }
 
@@ -271,139 +270,88 @@ impl NearAiProvider {
         }
     }
 
-    /// Inner request implementation with retry logic for transient errors.
-    ///
-    /// Retries on HTTP 429, 500, 502, 503, 504 with exponential backoff.
-    /// Does not retry on client errors (400, 401, 403, 404) or parse errors.
+    /// Inner request implementation without retry logic.
     async fn send_request_inner<T: Serialize + std::fmt::Debug, R: for<'de> Deserialize<'de>>(
         &self,
         path: &str,
         body: &T,
     ) -> Result<R, LlmError> {
         let url = self.api_url(path);
-        let max_retries = self.config.max_retries;
+        let token = self.session.get_token().await?;
 
-        for attempt in 0..=max_retries {
-            let token = self.session.get_token().await?;
+        tracing::debug!("Sending request to NEAR AI: {}", url);
+        tracing::debug!("Request body: {:?}", body);
 
-            tracing::debug!(
-                "Sending request to NEAR AI: {} (attempt {})",
-                url,
-                attempt + 1
-            );
-            tracing::debug!("Request body: {:?}", body);
+        let response = self
+            .client
+            .post(&url)
+            .header("Authorization", format!("Bearer {}", token.expose_secret()))
+            .header("Content-Type", "application/json")
+            .json(body)
+            .send()
+            .await
+            .map_err(|e| {
+                tracing::error!("NEAR AI request failed: {}", e);
+                e
+            })?;
 
-            let response = self
-                .client
-                .post(&url)
-                .header("Authorization", format!("Bearer {}", token.expose_secret()))
-                .header("Content-Type", "application/json")
-                .json(body)
-                .send()
-                .await;
+        let status = response.status();
+        let response_text = response.text().await.unwrap_or_default();
 
-            let response = match response {
-                Ok(r) => r,
-                Err(e) => {
-                    tracing::error!("NEAR AI request failed: {}", e);
-                    // Network errors (timeout, connection refused) are transient
-                    if attempt < max_retries {
-                        let delay = retry_backoff_delay(attempt);
-                        tracing::warn!(
-                            "NEAR AI request error (attempt {}/{}), retrying in {:?}: {}",
-                            attempt + 1,
-                            max_retries + 1,
-                            delay,
-                            e,
-                        );
-                        tokio::time::sleep(delay).await;
-                        continue;
-                    }
-                    return Err(e.into());
-                }
-            };
+        tracing::debug!("NEAR AI response status: {}", status);
+        tracing::debug!("NEAR AI response body: {}", response_text);
 
-            let status = response.status();
-            let response_text = response.text().await.unwrap_or_default();
+        if !status.is_success() {
+            // Check for session expiration (401 with specific message patterns)
+            if status.as_u16() == 401 {
+                let is_session_expired = response_text.to_lowercase().contains("session")
+                    && (response_text.to_lowercase().contains("expired")
+                        || response_text.to_lowercase().contains("invalid"));
 
-            tracing::debug!("NEAR AI response status: {}", status);
-            tracing::debug!("NEAR AI response body: {}", response_text);
-
-            if !status.is_success() {
-                let status_code = status.as_u16();
-
-                // Check for session expiration (401 with specific message patterns)
-                if status_code == 401 {
-                    let lower = response_text.to_lowercase();
-                    let is_session_expired = lower.contains("session")
-                        && (lower.contains("expired") || lower.contains("invalid"));
-
-                    if is_session_expired {
-                        return Err(LlmError::SessionExpired {
-                            provider: "nearai".to_string(),
-                        });
-                    }
-
-                    // Generic 401 -- not retryable
-                    return Err(LlmError::AuthFailed {
+                if is_session_expired {
+                    return Err(LlmError::SessionExpired {
                         provider: "nearai".to_string(),
                     });
                 }
 
-                // Check if this is a transient error worth retrying
-                if is_retryable_status(status_code) && attempt < max_retries {
-                    let delay = retry_backoff_delay(attempt);
-                    tracing::warn!(
-                        "NEAR AI returned HTTP {} (attempt {}/{}), retrying in {:?}",
-                        status_code,
-                        attempt + 1,
-                        max_retries + 1,
-                        delay,
-                    );
-                    tokio::time::sleep(delay).await;
-                    continue;
-                }
-
-                // Non-retryable error or exhausted retries
-                if let Ok(error) = serde_json::from_str::<NearAiErrorResponse>(&response_text) {
-                    if status_code == 429 {
-                        return Err(LlmError::RateLimited {
-                            provider: "nearai".to_string(),
-                            retry_after: None,
-                        });
-                    }
-                    return Err(LlmError::RequestFailed {
-                        provider: "nearai".to_string(),
-                        reason: error.error,
-                    });
-                }
-
-                return Err(LlmError::RequestFailed {
+                // Generic 401 without session expiration indication
+                return Err(LlmError::AuthFailed {
                     provider: "nearai".to_string(),
-                    reason: format!("HTTP {}: {}", status, response_text),
                 });
             }
 
-            // Success -- parse the response
-            return match serde_json::from_str::<R>(&response_text) {
-                Ok(parsed) => Ok(parsed),
-                Err(e) => {
-                    tracing::debug!("Response is not expected JSON format: {}", e);
-                    tracing::debug!("Will try alternative parsing in caller");
-                    Err(LlmError::InvalidResponse {
+            // Try to parse as JSON error
+            if let Ok(error) = serde_json::from_str::<NearAiErrorResponse>(&response_text) {
+                if status.as_u16() == 429 {
+                    return Err(LlmError::RateLimited {
                         provider: "nearai".to_string(),
-                        reason: format!("Parse error: {}. Raw: {}", e, response_text),
-                    })
+                        retry_after: None,
+                    });
                 }
-            };
+                return Err(LlmError::RequestFailed {
+                    provider: "nearai".to_string(),
+                    reason: error.error,
+                });
+            }
+
+            return Err(LlmError::RequestFailed {
+                provider: "nearai".to_string(),
+                reason: format!("HTTP {}: {}", status, response_text),
+            });
         }
 
-        // This is unreachable because the loop always returns, but the compiler
-        // cannot prove that. Return a generic error as a safety net.
-        Err(LlmError::RequestFailed {
-            provider: "nearai".to_string(),
-            reason: "retry loop exited unexpectedly".to_string(),
-        })
+        // Try to parse as our expected type
+        match serde_json::from_str::<R>(&response_text) {
+            Ok(parsed) => Ok(parsed),
+            Err(e) => {
+                tracing::debug!("Response is not expected JSON format: {}", e);
+                tracing::debug!("Will try alternative parsing in caller");
+                Err(LlmError::InvalidResponse {
+                    provider: "nearai".to_string(),
+                    reason: format!("Parse error: {}. Raw: {}", e, response_text),
+                })
+            }
+        }
     }
 }
 
@@ -508,7 +456,7 @@ impl LlmProvider for NearAiProvider {
             Err(e) => return Err(e),
         };
 
-        tracing::debug!("NEAR AI response: output_items={}", response.output.len());
+        tracing::debug!("NEAR AI response: {:?}", response);
 
         // Extract text from response output
         // Try multiple formats since API response shape may vary
@@ -516,6 +464,11 @@ impl LlmProvider for NearAiProvider {
             .output
             .iter()
             .filter_map(|item| {
+                tracing::debug!(
+                    "Processing output item: type={}, text={:?}",
+                    item.item_type,
+                    item.text
+                );
                 if item.item_type == "message" {
                     // First check for direct text field on item
                     if let Some(ref text) = item.text {
@@ -526,6 +479,11 @@ impl LlmProvider for NearAiProvider {
                         contents
                             .iter()
                             .filter_map(|c| {
+                                tracing::debug!(
+                                    "Content item: type={}, text={:?}",
+                                    c.content_type,
+                                    c.text
+                                );
                                 // Accept various content types that might contain text
                                 match c.content_type.as_str() {
                                     "output_text" | "text" => c.text.clone(),
@@ -736,21 +694,21 @@ impl LlmProvider for NearAiProvider {
                         }
                     }
                 }
-            } else if item.item_type == "function_call"
-                && let (Some(name), Some(call_id)) = (&item.name, &item.call_id)
-            {
-                // Parse arguments JSON string into Value
-                let arguments = item
-                    .arguments
-                    .as_ref()
-                    .and_then(|s| serde_json::from_str(s).ok())
-                    .unwrap_or(serde_json::Value::Object(Default::default()));
+            } else if item.item_type == "function_call" {
+                if let (Some(name), Some(call_id)) = (&item.name, &item.call_id) {
+                    // Parse arguments JSON string into Value
+                    let arguments = item
+                        .arguments
+                        .as_ref()
+                        .and_then(|s| serde_json::from_str(s).ok())
+                        .unwrap_or(serde_json::Value::Object(Default::default()));
 
-                tool_calls.push(ToolCall {
-                    id: call_id.clone(),
-                    name: name.clone(),
-                    arguments,
-                });
+                    tool_calls.push(ToolCall {
+                        id: call_id.clone(),
+                        name: name.clone(),
+                        arguments,
+                    });
+                }
             }
         }
 

src/llm/nearai_chat.rs

@@ -16,7 +16,6 @@ use crate::llm::provider::{
     ChatMessage, CompletionRequest, CompletionResponse, FinishReason, LlmProvider, ModelMetadata,
     Role, ToolCall, ToolCompletionRequest, ToolCompletionResponse,
 };
-use crate::llm::retry::{is_retryable_status, retry_backoff_delay};
 
 /// NEAR AI Chat Completions API provider.
 pub struct NearAiChatProvider {
@@ -63,116 +62,63 @@ impl NearAiChatProvider {
             .unwrap_or_default()
     }
 
-    /// Send a request to the chat completions API with retry on transient errors.
-    ///
-    /// Retries on HTTP 429, 500, 502, 503, 504 with exponential backoff.
-    /// Does not retry on client errors (400, 401, 403, 404) or parse errors.
+    /// Send a request to the chat completions API.
     async fn send_request<T: Serialize, R: for<'de> Deserialize<'de>>(
         &self,
         body: &T,
     ) -> Result<R, LlmError> {
         let url = self.api_url("chat/completions");
-        let max_retries = self.config.max_retries;
 
-        for attempt in 0..=max_retries {
-            tracing::debug!(
-                "Sending request to NEAR AI Chat: {} (attempt {})",
-                url,
-                attempt + 1,
-            );
+        tracing::debug!("Sending request to NEAR AI Chat: {}", url);
 
-            if tracing::enabled!(tracing::Level::DEBUG)
-                && let Ok(json) = serde_json::to_string(body)
-            {
-                tracing::debug!("NEAR AI Chat request body: {}", json);
-            }
+        // Log the request body for debugging tool call issues
+        if let Ok(json) = serde_json::to_string(body) {
+            tracing::debug!("NEAR AI Chat request body: {}", json);
+        }
 
-            let response = self
-                .client
-                .post(&url)
-                .header("Authorization", format!("Bearer {}", self.api_key()))
-                .header("Content-Type", "application/json")
-                .json(body)
-                .send()
-                .await;
-
-            let response = match response {
-                Ok(r) => r,
-                Err(e) => {
-                    tracing::error!("NEAR AI Chat request failed: {}", e);
-                    if attempt < max_retries {
-                        let delay = retry_backoff_delay(attempt);
-                        tracing::warn!(
-                            "NEAR AI Chat request error (attempt {}/{}), retrying in {:?}: {}",
-                            attempt + 1,
-                            max_retries + 1,
-                            delay,
-                            e,
-                        );
-                        tokio::time::sleep(delay).await;
-                        continue;
-                    }
-                    return Err(LlmError::RequestFailed {
-                        provider: "nearai_chat".to_string(),
-                        reason: e.to_string(),
-                    });
+        let response = self
+            .client
+            .post(&url)
+            .header("Authorization", format!("Bearer {}", self.api_key()))
+            .header("Content-Type", "application/json")
+            .json(body)
+            .send()
+            .await
+            .map_err(|e| {
+                tracing::error!("NEAR AI Chat request failed: {}", e);
+                LlmError::RequestFailed {
+                    provider: "nearai_chat".to_string(),
+                    reason: e.to_string(),
                 }
-            };
-
-            let status = response.status();
-            let response_text = response.text().await.unwrap_or_default();
+            })?;
 
-            tracing::debug!("NEAR AI Chat response status: {}", status);
-            tracing::debug!("NEAR AI Chat response body: {}", response_text);
+        let status = response.status();
+        let response_text = response.text().await.unwrap_or_default();
 
-            if !status.is_success() {
-                let status_code = status.as_u16();
-
-                // Auth errors are not retryable
-                if status_code == 401 {
-                    return Err(LlmError::AuthFailed {
-                        provider: "nearai_chat".to_string(),
-                    });
-                }
+        tracing::debug!("NEAR AI Chat response status: {}", status);
+        tracing::debug!("NEAR AI Chat response body: {}", response_text);
 
-                // Transient errors: retry with backoff
-                if is_retryable_status(status_code) && attempt < max_retries {
-                    let delay = retry_backoff_delay(attempt);
-                    tracing::warn!(
-                        "NEAR AI Chat returned HTTP {} (attempt {}/{}), retrying in {:?}",
-                        status_code,
-                        attempt + 1,
-                        max_retries + 1,
-                        delay,
-                    );
-                    tokio::time::sleep(delay).await;
-                    continue;
-                }
-
-                // Non-retryable or exhausted retries
-                if status_code == 429 {
-                    return Err(LlmError::RateLimited {
-                        provider: "nearai_chat".to_string(),
-                        retry_after: None,
-                    });
-                }
-                return Err(LlmError::RequestFailed {
+        if !status.is_success() {
+            if status.as_u16() == 401 {
+                return Err(LlmError::AuthFailed {
                     provider: "nearai_chat".to_string(),
-                    reason: format!("HTTP {}: {}", status, response_text),
                 });
             }
-
-            // Success — parse the response
-            return serde_json::from_str(&response_text).map_err(|e| LlmError::InvalidResponse {
+            if status.as_u16() == 429 {
+                return Err(LlmError::RateLimited {
+                    provider: "nearai_chat".to_string(),
+                    retry_after: None,
+                });
+            }
+            return Err(LlmError::RequestFailed {
                 provider: "nearai_chat".to_string(),
-                reason: format!("JSON parse error: {}. Raw: {}", e, response_text),
+                reason: format!("HTTP {}: {}", status, response_text),
             });
         }
 
-        // Safety net: unreachable because the loop always returns
-        Err(LlmError::RequestFailed {
+        serde_json::from_str(&response_text).map_err(|e| LlmError::InvalidResponse {
             provider: "nearai_chat".to_string(),
-            reason: "retry loop exited unexpectedly".to_string(),
+            reason: format!("JSON parse error: {}. Raw: {}", e, response_text),
         })
     }
 
@@ -449,10 +395,10 @@ fn flatten_tool_messages(messages: Vec<ChatCompletionMessage>) -> Vec<ChatComple
             if let (true, Some(calls)) = (msg.role == "assistant", &msg.tool_calls) {
                 // Convert assistant tool_calls into descriptive text
                 let mut parts: Vec<String> = Vec::new();
-                if let Some(ref text) = msg.content
-                    && !text.is_empty()
-                {
-                    parts.push(text.clone());
+                if let Some(ref text) = msg.content {
+                    if !text.is_empty() {
+                        parts.push(text.clone());
+                    }
                 }
                 for tc in calls {
                     parts.push(format!(

src/llm/reasoning.rs

@@ -113,12 +113,6 @@ pub struct ToolSelection {
     pub reasoning: String,
     /// Alternative tools considered.
     pub alternatives: Vec<String>,
-    /// The tool call ID from the LLM response.
-    ///
-    /// OpenAI-compatible providers assign each tool call a unique ID that must
-    /// be echoed back in the corresponding tool result message. Without this,
-    /// the provider cannot match results to their originating calls.
-    pub tool_call_id: String,
 }
 
 /// Token usage from a single LLM call.
@@ -250,7 +244,6 @@ impl Reasoning {
                 parameters: tool_call.arguments,
                 reasoning: reasoning.clone(),
                 alternatives: vec![],
-                tool_call_id: tool_call.id,
             })
             .collect();
 
@@ -588,20 +581,21 @@ fn recover_tool_calls_from_content(
             }
 
             // Try JSON first: {"name":"x","arguments":{}}
-            if let Ok(parsed) = serde_json::from_str::<serde_json::Value>(inner)
-                && let Some(name) = parsed.get("name").and_then(|v| v.as_str())
-                && tool_names.contains(name)
-            {
-                let arguments = parsed
-                    .get("arguments")
-                    .cloned()
-                    .unwrap_or(serde_json::Value::Object(Default::default()));
-                calls.push(ToolCall {
-                    id: format!("recovered_{}", calls.len()),
-                    name: name.to_string(),
-                    arguments,
-                });
-                continue;
+            if let Ok(parsed) = serde_json::from_str::<serde_json::Value>(inner) {
+                if let Some(name) = parsed.get("name").and_then(|v| v.as_str()) {
+                    if tool_names.contains(name) {
+                        let arguments = parsed
+                            .get("arguments")
+                            .cloned()
+                            .unwrap_or(serde_json::Value::Object(Default::default()));
+                        calls.push(ToolCall {
+                            id: format!("recovered_{}", calls.len()),
+                            name: name.to_string(),
+                            arguments,
+                        });
+                        continue;
+                    }
+                }
             }
 
             // Bare tool name (e.g. "<tool_call>tool_list</tool_call>")

src/llm/retry.rs

@@ -1,96 +0,0 @@
-//! Shared retry helpers for LLM providers.
-//!
-//! Provides exponential backoff with jitter and retryable status classification
-//! used by both `NearAiProvider` and `NearAiChatProvider`.
-
-use std::time::Duration;
-
-use rand::Rng;
-
-/// Returns `true` if the HTTP status code is transient and worth retrying.
-pub(crate) fn is_retryable_status(status: u16) -> bool {
-    matches!(status, 429 | 500 | 502 | 503 | 504)
-}
-
-/// Calculate exponential backoff delay with random jitter.
-///
-/// Base delay is 1 second, doubled each attempt, with +/-25% jitter.
-/// - attempt 0: ~1s (0.75s - 1.25s)
-/// - attempt 1: ~2s (1.5s - 2.5s)
-/// - attempt 2: ~4s (3.0s - 5.0s)
-pub(crate) fn retry_backoff_delay(attempt: u32) -> Duration {
-    let base_ms: u64 = 1000u64.saturating_mul(2u64.saturating_pow(attempt));
-    let jitter_range = base_ms / 4; // 25%
-    let jitter = if jitter_range > 0 {
-        let offset = rand::thread_rng().gen_range(0..=jitter_range * 2);
-        offset as i64 - jitter_range as i64
-    } else {
-        0
-    };
-    let delay_ms = (base_ms as i64 + jitter).max(100) as u64;
-    Duration::from_millis(delay_ms)
-}
-
-#[cfg(test)]
-mod tests {
-    use super::*;
-
-    #[test]
-    fn test_is_retryable_status() {
-        // Transient errors should be retryable
-        assert!(is_retryable_status(429));
-        assert!(is_retryable_status(500));
-        assert!(is_retryable_status(502));
-        assert!(is_retryable_status(503));
-        assert!(is_retryable_status(504));
-
-        // Client errors should not be retryable
-        assert!(!is_retryable_status(400));
-        assert!(!is_retryable_status(401));
-        assert!(!is_retryable_status(403));
-        assert!(!is_retryable_status(404));
-        assert!(!is_retryable_status(422));
-
-        // Success codes should not be retryable
-        assert!(!is_retryable_status(200));
-        assert!(!is_retryable_status(201));
-    }
-
-    #[test]
-    fn test_retry_backoff_delay_exponential_growth() {
-        // Run multiple samples to verify the range, accounting for jitter
-        for _ in 0..20 {
-            let d0 = retry_backoff_delay(0);
-            let d1 = retry_backoff_delay(1);
-            let d2 = retry_backoff_delay(2);
-
-            // Attempt 0: base 1000ms, jitter +/-250ms -> [750, 1250]
-            assert!(d0.as_millis() >= 750, "attempt 0 too low: {:?}", d0);
-            assert!(d0.as_millis() <= 1250, "attempt 0 too high: {:?}", d0);
-
-            // Attempt 1: base 2000ms, jitter +/-500ms -> [1500, 2500]
-            assert!(d1.as_millis() >= 1500, "attempt 1 too low: {:?}", d1);
-            assert!(d1.as_millis() <= 2500, "attempt 1 too high: {:?}", d1);
-
-            // Attempt 2: base 4000ms, jitter +/-1000ms -> [3000, 5000]
-            assert!(d2.as_millis() >= 3000, "attempt 2 too low: {:?}", d2);
-            assert!(d2.as_millis() <= 5000, "attempt 2 too high: {:?}", d2);
-        }
-    }
-
-    #[test]
-    fn test_retry_backoff_delay_minimum() {
-        // Even at attempt 0, delay should be at least 100ms (the minimum floor)
-        for _ in 0..20 {
-            let delay = retry_backoff_delay(0);
-            assert!(delay.as_millis() >= 100);
-        }
-    }
-
-    #[test]
-    fn test_retry_backoff_delay_no_overflow() {
-        // Very high attempt numbers should not panic from overflow
-        let delay = retry_backoff_delay(30);
-        assert!(delay.as_millis() >= 100);
-    }
-}

src/llm/session.rs

@@ -31,6 +31,8 @@ pub struct SessionConfig {
     pub auth_base_url: String,
     /// Path to session file (e.g., ~/.ironclaw/session.json).
     pub session_path: PathBuf,
+    /// Port range for OAuth callback server.
+    pub callback_port_range: (u16, u16),
 }
 
 impl Default for SessionConfig {
@@ -38,6 +40,7 @@ impl Default for SessionConfig {
         Self {
             auth_base_url: "https://private.near.ai".to_string(),
             session_path: default_session_path(),
+            callback_port_range: (9876, 9886),
         }
     }
 }
@@ -80,16 +83,16 @@ impl SessionManager {
         };
 
         // Try to load existing session synchronously during construction
-        if let Ok(data) = std::fs::read_to_string(&manager.config.session_path)
-            && let Ok(session) = serde_json::from_str::<SessionData>(&data)
-        {
-            // We can't await here, so we use try_write
-            if let Ok(mut guard) = manager.token.try_write() {
-                *guard = Some(SecretString::from(session.session_token));
-                tracing::info!(
-                    "Loaded session token from {}",
-                    manager.config.session_path.display()
-                );
+        if let Ok(data) = std::fs::read_to_string(&manager.config.session_path) {
+            if let Ok(session) = serde_json::from_str::<SessionData>(&data) {
+                // We can't await here, so we use try_write
+                if let Ok(mut guard) = manager.token.try_write() {
+                    *guard = Some(SecretString::from(session.session_token));
+                    tracing::info!(
+                        "Loaded session token from {}",
+                        manager.config.session_path.display()
+                    );
+                }
             }
         }
 
@@ -219,21 +222,38 @@ impl SessionManager {
 
     /// Start the OAuth login flow.
     ///
-    /// 1. Bind the fixed callback port
+    /// 1. Find an available port for the callback server
     /// 2. Print the auth URL and attempt to open browser
     /// 3. Wait for OAuth callback with session token
     /// 4. Save and return the token
     async fn initiate_login(&self) -> Result<(), LlmError> {
-        use crate::cli::oauth_defaults::{self, OAUTH_CALLBACK_PORT};
+        use tokio::io::{AsyncBufReadExt, AsyncWriteExt, BufReader};
+        use tokio::net::TcpListener;
 
-        let listener = oauth_defaults::bind_callback_listener()
-            .await
-            .map_err(|e| LlmError::SessionRenewalFailed {
-                provider: "nearai".to_string(),
-                reason: e.to_string(),
-            })?;
+        // Find an available port
+        let mut listener = None;
+        let mut port = 0;
 
-        let callback_url = format!("http://127.0.0.1:{}", OAUTH_CALLBACK_PORT);
+        for p in self.config.callback_port_range.0..=self.config.callback_port_range.1 {
+            match TcpListener::bind(format!("127.0.0.1:{}", p)).await {
+                Ok(l) => {
+                    listener = Some(l);
+                    port = p;
+                    break;
+                }
+                Err(_) => continue,
+            }
+        }
+
+        let listener = listener.ok_or_else(|| LlmError::SessionRenewalFailed {
+            provider: "nearai".to_string(),
+            reason: format!(
+                "Could not find available port in range {}-{}",
+                self.config.callback_port_range.0, self.config.callback_port_range.1
+            ),
+        })?;
+
+        let callback_url = format!("http://127.0.0.1:{}", port);
 
         // Show auth provider menu
         println!();
@@ -313,16 +333,138 @@ impl SessionManager {
         println!();
         println!("Waiting for authentication...");
 
-        // The NEAR AI API redirects to: {frontend_callback}/auth/callback?token=X&...
-        let session_token =
-            oauth_defaults::wait_for_callback(listener, "/auth/callback", "token", "NEAR AI")
-                .await
-                .map_err(|e| LlmError::SessionRenewalFailed {
-                    provider: "nearai".to_string(),
-                    reason: e.to_string(),
+        // Wait for callback with timeout
+        // The API redirects to: {frontend_callback}/auth/callback?token=X&session_id=X&expires_at=X&is_new_user=X
+        let timeout = std::time::Duration::from_secs(300); // 5 minutes
+        let selected_provider = auth_provider.to_string();
+        let (session_token, auth_provider) = tokio::time::timeout(timeout, async move {
+            loop {
+                let (mut socket, _) = listener.accept().await.map_err(|e| {
+                    LlmError::SessionRenewalFailed {
+                        provider: "nearai".to_string(),
+                        reason: format!("Failed to accept connection: {}", e),
+                    }
                 })?;
 
-        let auth_provider = Some(auth_provider.to_string());
+                let mut reader = BufReader::new(&mut socket);
+                let mut request_line = String::new();
+                reader.read_line(&mut request_line).await.map_err(|e| {
+                    LlmError::SessionRenewalFailed {
+                        provider: "nearai".to_string(),
+                        reason: format!("Failed to read request: {}", e),
+                    }
+                })?;
+
+                // Parse GET /auth/callback?token=xxx&session_id=xxx&expires_at=xxx&is_new_user=xxx HTTP/1.1
+                if let Some(path) = request_line.split_whitespace().nth(1) {
+                    if path.starts_with("/auth/callback") {
+                        // Parse query parameters
+                        if let Some(query) = path.split('?').nth(1) {
+                            let mut token = None;
+
+                            for param in query.split('&') {
+                                let parts: Vec<&str> = param.splitn(2, '=').collect();
+                                if parts.len() == 2 && parts[0] == "token" {
+                                    token = Some(
+                                        urlencoding::decode(parts[1])
+                                            .unwrap_or_else(|_| parts[1].into())
+                                            .into_owned(),
+                                    );
+                                }
+                            }
+
+                            if let Some(token) = token {
+                                // Send success response with nice styling
+                                let response = concat!(
+                                    "HTTP/1.1 200 OK\r\n",
+                                    "Content-Type: text/html; charset=utf-8\r\n",
+                                    "Connection: close\r\n",
+                                    "\r\n",
+                                    "<!DOCTYPE html>\n",
+                                    "<html>\n",
+                                    "<head>\n",
+                                    "  <meta charset=\"utf-8\">\n",
+                                    "  <title>NEAR AI - Authentication Successful</title>\n",
+                                    "  <style>\n",
+                                    "    * { margin: 0; padding: 0; box-sizing: border-box; }\n",
+                                    "    body {\n",
+                                    "      font-family: -apple-system, BlinkMacSystemFont, 'Segoe UI', Roboto, sans-serif;\n",
+                                    "      background: linear-gradient(135deg, #1a1a2e 0%, #16213e 100%);\n",
+                                    "      min-height: 100vh;\n",
+                                    "      display: flex;\n",
+                                    "      align-items: center;\n",
+                                    "      justify-content: center;\n",
+                                    "      color: #fff;\n",
+                                    "    }\n",
+                                    "    .container {\n",
+                                    "      text-align: center;\n",
+                                    "      padding: 3rem;\n",
+                                    "      background: rgba(255,255,255,0.05);\n",
+                                    "      border-radius: 16px;\n",
+                                    "      backdrop-filter: blur(10px);\n",
+                                    "      border: 1px solid rgba(255,255,255,0.1);\n",
+                                    "      max-width: 400px;\n",
+                                    "    }\n",
+                                    "    .checkmark {\n",
+                                    "      width: 80px;\n",
+                                    "      height: 80px;\n",
+                                    "      background: linear-gradient(135deg, #00d9a5 0%, #00b386 100%);\n",
+                                    "      border-radius: 50%;\n",
+                                    "      display: flex;\n",
+                                    "      align-items: center;\n",
+                                    "      justify-content: center;\n",
+                                    "      margin: 0 auto 1.5rem;\n",
+                                    "      font-size: 40px;\n",
+                                    "    }\n",
+                                    "    h1 {\n",
+                                    "      font-size: 1.5rem;\n",
+                                    "      font-weight: 600;\n",
+                                    "      margin-bottom: 0.75rem;\n",
+                                    "    }\n",
+                                    "    p {\n",
+                                    "      color: rgba(255,255,255,0.7);\n",
+                                    "      font-size: 0.95rem;\n",
+                                    "      line-height: 1.5;\n",
+                                    "    }\n",
+                                    "    .brand {\n",
+                                    "      margin-top: 2rem;\n",
+                                    "      padding-top: 1.5rem;\n",
+                                    "      border-top: 1px solid rgba(255,255,255,0.1);\n",
+                                    "      font-size: 0.8rem;\n",
+                                    "      color: rgba(255,255,255,0.4);\n",
+                                    "    }\n",
+                                    "  </style>\n",
+                                    "</head>\n",
+                                    "<body>\n",
+                                    "  <div class=\"container\">\n",
+                                    "    <div class=\"checkmark\">&#10003;</div>\n",
+                                    "    <h1>Authentication Successful</h1>\n",
+                                    "    <p>You can close this window and return to the terminal.</p>\n",
+                                    "    <div class=\"brand\">NEAR AI Agent</div>\n",
+                                    "  </div>\n",
+                                    "</body>\n",
+                                    "</html>"
+                                );
+
+                                let _ = socket.write_all(response.as_bytes()).await;
+                                let _ = socket.shutdown().await;
+
+                                return Ok::<_, LlmError>((token, Some(selected_provider.clone())));
+                            }
+                        }
+                    }
+                }
+
+                // Not the callback we're looking for, send 404
+                let response = "HTTP/1.1 404 Not Found\r\nConnection: close\r\n\r\n";
+                let _ = socket.write_all(response.as_bytes()).await;
+            }
+        })
+        .await
+        .map_err(|_| LlmError::SessionRenewalFailed {
+            provider: "nearai".to_string(),
+            reason: "Authentication timed out after 5 minutes".to_string(),
+        })??;
 
         // Save the token
         self.save_session(&session_token, auth_provider.as_deref())
@@ -428,30 +570,17 @@ impl SessionManager {
             })?;
 
         let user_id = self.user_id.read().await.clone();
-        let value = if let Some(value) = store
+        let value = store
             .get_setting(&user_id, "nearai.session_token")
             .await
             .map_err(|e| LlmError::SessionRenewalFailed {
                 provider: "nearai".to_string(),
                 reason: format!("DB query failed: {}", e),
-            })? {
-            value
-        } else {
-            tracing::warn!(
-                "nearai.session_token missing; falling back to legacy nearai.session for backwards compatibility"
-            );
-            store
-                .get_setting(&user_id, "nearai.session")
-                .await
-                .map_err(|e| LlmError::SessionRenewalFailed {
-                    provider: "nearai".to_string(),
-                    reason: format!("DB query failed: {}", e),
-                })?
-                .ok_or(LlmError::SessionRenewalFailed {
-                    provider: "nearai".to_string(),
-                    reason: "No session in DB".to_string(),
-                })?
-        };
+            })?
+            .ok_or_else(|| LlmError::SessionRenewalFailed {
+                provider: "nearai".to_string(),
+                reason: "No session in DB".to_string(),
+            })?;
 
         let session: SessionData =
             serde_json::from_value(value).map_err(|e| LlmError::SessionRenewalFailed {
@@ -513,14 +642,15 @@ pub async fn create_session_manager(config: SessionConfig) -> Arc<SessionManager
     let manager = SessionManager::new_async(config).await;
 
     // Check for legacy env var and migrate if present and no file token
-    if !manager.has_token().await
-        && let Ok(token) = std::env::var("NEARAI_SESSION_TOKEN")
-        && !token.is_empty()
-    {
-        tracing::info!("Migrating session token from NEARAI_SESSION_TOKEN env var to file");
-        manager.set_token(SecretString::from(token.clone())).await;
-        if let Err(e) = manager.save_session(&token, None).await {
-            tracing::warn!("Failed to save migrated session: {}", e);
+    if !manager.has_token().await {
+        if let Ok(token) = std::env::var("NEARAI_SESSION_TOKEN") {
+            if !token.is_empty() {
+                tracing::info!("Migrating session token from NEARAI_SESSION_TOKEN env var to file");
+                manager.set_token(SecretString::from(token.clone())).await;
+                if let Err(e) = manager.save_session(&token, None).await {
+                    tracing::warn!("Failed to save migrated session: {}", e);
+                }
+            }
         }
     }
 
@@ -541,6 +671,7 @@ mod tests {
         let config = SessionConfig {
             auth_base_url: "https://example.com".to_string(),
             session_path: session_path.clone(),
+            callback_port_range: (9900, 9910),
         };
 
         let manager = SessionManager::new_async(config.clone()).await;
@@ -581,6 +712,7 @@ mod tests {
         let config = SessionConfig {
             auth_base_url: "https://example.com".to_string(),
             session_path: dir.path().join("nonexistent.json"),
+            callback_port_range: (9900, 9910),
         };
 
         let manager = SessionManager::new_async(config).await;

src/main.rs

@@ -22,11 +22,7 @@ use ironclaw::{
     config::Config,
     context::ContextManager,
     extensions::ExtensionManager,
-    hooks::HookRegistry,
-    llm::{
-        CooldownConfig, FailoverProvider, LlmProvider, SessionConfig, create_cheap_llm_provider,
-        create_llm_provider, create_llm_provider_with_config, create_session_manager,
-    },
+    llm::{SessionConfig, create_llm_provider, create_session_manager},
     orchestrator::{
         ContainerJobConfig, ContainerJobManager, OrchestratorApi, TokenStore,
         api::OrchestratorState,
@@ -49,6 +45,7 @@ use ironclaw::secrets::PostgresSecretsStore;
 use ironclaw::secrets::SecretsCrypto;
 #[cfg(any(feature = "postgres", feature = "libsql"))]
 use ironclaw::setup::{SetupConfig, SetupWizard};
+
 #[tokio::main]
 async fn main() -> anyhow::Result<()> {
     let cli = Cli::parse();
@@ -93,6 +90,7 @@ async fn main() -> anyhow::Result<()> {
                 .init();
 
             // Memory commands need database (and optionally embeddings)
+            let _ = dotenvy::dotenv();
             let config = Config::from_env()
                 .await
                 .map_err(|e| anyhow::anyhow!("{}", e))?;
@@ -101,6 +99,7 @@ async fn main() -> anyhow::Result<()> {
             let session = ironclaw::llm::create_session_manager(ironclaw::llm::SessionConfig {
                 auth_base_url: config.llm.nearai.auth_base_url.clone(),
                 session_path: config.llm.nearai.session_path.clone(),
+                ..Default::default()
             })
             .await;
 
@@ -153,6 +152,7 @@ async fn main() -> anyhow::Result<()> {
             return run_pairing_command(pairing_cmd.clone()).map_err(|e| anyhow::anyhow!("{}", e));
         }
         Some(Command::Status) => {
+            let _ = dotenvy::dotenv();
             tracing_subscriber::fmt()
                 .with_env_filter(
                     EnvFilter::try_from_default_env().unwrap_or_else(|_| EnvFilter::new("warn")),
@@ -243,10 +243,8 @@ async fn main() -> anyhow::Result<()> {
             skip_auth,
             channels_only,
         }) => {
-            // Load .env files before running onboarding wizard.
-            // Standard ./.env first (higher priority), then ~/.ironclaw/.env.
+            // Load .env before running onboarding wizard
             let _ = dotenvy::dotenv();
-            ironclaw::bootstrap::load_ironclaw_env();
 
             #[cfg(any(feature = "postgres", feature = "libsql"))]
             {
@@ -269,23 +267,23 @@ async fn main() -> anyhow::Result<()> {
         }
     }
 
-    // Load .env files early so DATABASE_URL (and any other vars) are
-    // available to all subsequent env-based config resolution.
-    // Standard ./.env first (higher priority), then ~/.ironclaw/.env.
+    // Load .env if present
     let _ = dotenvy::dotenv();
-    ironclaw::bootstrap::load_ironclaw_env();
 
     // Enhanced first-run detection
     #[cfg(any(feature = "postgres", feature = "libsql"))]
-    if !cli.no_onboard
-        && let Some(reason) = check_onboard_needed()
-    {
-        println!("Onboarding needed: {}", reason);
-        println!();
-        let mut wizard = SetupWizard::new();
-        wizard.run().await?;
+    if !cli.no_onboard {
+        if let Some(reason) = check_onboard_needed().await {
+            println!("Onboarding needed: {}", reason);
+            println!();
+            let mut wizard = SetupWizard::new();
+            wizard.run().await?;
+        }
     }
 
+    // Load bootstrap config (4 fields that must live on disk)
+    let bootstrap = ironclaw::bootstrap::BootstrapConfig::load();
+
     // Load initial config from env + disk (before DB is available)
     let mut config = match Config::from_env().await {
         Ok(c) => c,
@@ -305,20 +303,18 @@ async fn main() -> anyhow::Result<()> {
     let session_config = SessionConfig {
         auth_base_url: config.llm.nearai.auth_base_url.clone(),
         session_path: config.llm.nearai.session_path.clone(),
+        ..Default::default()
     };
     let session = create_session_manager(session_config).await;
 
-    // Session-based auth is only needed for NEAR AI backend without an API key.
-    // ChatCompletions mode with an API key skips session auth entirely.
-    if config.llm.backend == ironclaw::config::LlmBackend::NearAi
-        && config.llm.nearai.api_key.is_none()
-    {
+    // Ensure we're authenticated before proceeding (only needed for NEAR AI backend)
+    if config.llm.backend == ironclaw::config::LlmBackend::NearAi {
         session.ensure_authenticated().await?;
     }
 
     // Initialize tracing
     let env_filter = EnvFilter::try_from_default_env()
-        .unwrap_or_else(|_| EnvFilter::new("ironclaw=info,tower_http=warn"));
+        .unwrap_or_else(|_| EnvFilter::new("ironclaw=info,tower_http=debug"));
 
     // Create log broadcaster before tracing init so the WebLogLayer can capture all events.
     // This gets wired to the gateway's /api/logs/events SSE endpoint later.
@@ -326,11 +322,7 @@ async fn main() -> anyhow::Result<()> {
 
     tracing_subscriber::registry()
         .with(env_filter)
-        .with(
-            tracing_subscriber::fmt::layer()
-                .with_target(false)
-                .with_writer(ironclaw::tracing_fmt::TruncatingStderr::default()),
-        )
+        .with(tracing_subscriber::fmt::layer().with_target(false))
         .with(WebLogLayer::new(Arc::clone(&log_broadcaster)))
         .init();
 
@@ -338,10 +330,7 @@ async fn main() -> anyhow::Result<()> {
     let repl_channel = if let Some(ref msg) = cli.message {
         Some(ReplChannel::with_message(msg.clone()))
     } else if config.channels.cli.enabled {
-        let repl = ReplChannel::new();
-        // Suppress the one-liner banner; boot screen will be shown instead.
-        repl.suppress_banner();
-        Some(repl)
+        Some(ReplChannel::new())
     } else {
         None
     };
@@ -429,7 +418,7 @@ async fn main() -> anyhow::Result<()> {
         }
 
         // Reload config from DB now that we have a connection.
-        match Config::from_db(db.as_ref(), "default").await {
+        match Config::from_db(db.as_ref(), "default", &bootstrap).await {
             Ok(db_config) => {
                 config = db_config;
                 tracing::info!("Configuration reloaded from database");
@@ -450,112 +439,10 @@ async fn main() -> anyhow::Result<()> {
             tracing::warn!("Failed to cleanup stale sandbox jobs: {}", e);
         }
     }
-
-    // Create secrets store early: needed for injecting LLM API keys from encrypted
-    // storage before creating the LLM provider, and later for MCP auth + WASM channels.
-    //
-    // When both `postgres` and `libsql` features are compiled, the runtime-selected
-    // backend determines which store is created: whichever DB init branch ran will
-    // have set its handle (pg_pool or libsql_db), and the or_else chain picks it up.
-    let secrets_store: Option<Arc<dyn SecretsStore + Send + Sync>> =
-        if let Some(master_key) = config.secrets.master_key() {
-            match SecretsCrypto::new(master_key.clone()) {
-                Ok(crypto) => {
-                    let crypto = Arc::new(crypto);
-                    let store: Option<Arc<dyn SecretsStore + Send + Sync>> = None;
-
-                    #[cfg(feature = "libsql")]
-                    let store = store.or_else(|| {
-                        libsql_db.take().map(|db| {
-                            Arc::new(LibSqlSecretsStore::new(db, Arc::clone(&crypto)))
-                                as Arc<dyn SecretsStore + Send + Sync>
-                        })
-                    });
-
-                    #[cfg(feature = "postgres")]
-                    let store = store.or_else(|| {
-                        pg_pool.as_ref().map(|pool| {
-                            Arc::new(PostgresSecretsStore::new(pool.clone(), Arc::clone(&crypto)))
-                                as Arc<dyn SecretsStore + Send + Sync>
-                        })
-                    });
-
-                    store
-                }
-                Err(e) => {
-                    tracing::warn!("Failed to initialize secrets crypto: {}", e);
-                    #[cfg(feature = "libsql")]
-                    let _ = libsql_db.take();
-                    None
-                }
-            }
-        } else {
-            #[cfg(feature = "libsql")]
-            let _ = libsql_db.take();
-            None
-        };
-
-    // Inject LLM API keys from the encrypted secrets store into a thread-safe
-    // overlay so that optional_env() (used by LlmConfig::resolve()) picks them
-    // up. Then re-resolve LlmConfig with the newly available keys (backend may
-    // have been set during onboarding but the API key is in the secrets store).
-    if let Some(ref secrets) = secrets_store {
-        ironclaw::config::inject_llm_keys_from_secrets(secrets.as_ref(), "default").await;
-
-        // Re-resolve LlmConfig now that secrets overlay has been populated
-        if let Some(ref db_ref) = db {
-            match Config::from_db(db_ref.as_ref(), "default").await {
-                Ok(refreshed) => {
-                    config = refreshed;
-                    tracing::debug!("LlmConfig re-resolved after secret injection");
-                }
-                Err(e) => {
-                    tracing::warn!("Failed to re-resolve config after secret injection: {}", e);
-                }
-            }
-        }
-    }
-
     // Initialize LLM provider (clone session so we can reuse it for embeddings)
     let llm = create_llm_provider(&config.llm, 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) = config.llm.nearai.fallback_model.as_ref() {
-            if fallback_model == &config.llm.nearai.model {
-                tracing::warn!(
-                    "fallback_model is the same as primary model, failover may not be effective"
-                );
-            }
-            let mut fallback_config = config.llm.nearai.clone();
-            fallback_config.model = fallback_model.clone();
-            let fallback = create_llm_provider_with_config(&fallback_config, 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(
-                    config.llm.nearai.failover_cooldown_secs,
-                ),
-                failure_threshold: config.llm.nearai.failover_cooldown_threshold,
-            };
-            Arc::new(FailoverProvider::with_cooldown(
-                vec![llm, fallback],
-                cooldown_config,
-            )?)
-        } else {
-            llm
-        };
-
-    // Initialize cheap LLM provider for lightweight tasks (heartbeat, evaluation)
-    let cheap_llm = create_cheap_llm_provider(&config.llm, session.clone())?;
-    if let Some(ref cheap) = cheap_llm {
-        tracing::info!("Cheap LLM provider initialized: {}", cheap.model_name());
-    }
-
     // Initialize safety layer
     let safety = Arc::new(SafetyLayer::new(&config.safety));
     tracing::info!("Safety layer initialized");
@@ -629,6 +516,49 @@ async fn main() -> anyhow::Result<()> {
         tracing::info!("Builder mode enabled");
     }
 
+    // Create secrets store if master key is configured (needed for MCP auth and WASM channels).
+    //
+    // When both `postgres` and `libsql` features are compiled, the runtime-selected
+    // backend determines which store is created: whichever DB init branch ran will
+    // have set its handle (pg_pool or libsql_db), and the or_else chain picks it up.
+    let secrets_store: Option<Arc<dyn SecretsStore + Send + Sync>> =
+        if let Some(master_key) = config.secrets.master_key() {
+            match SecretsCrypto::new(master_key.clone()) {
+                Ok(crypto) => {
+                    let crypto = Arc::new(crypto);
+                    let store: Option<Arc<dyn SecretsStore + Send + Sync>> = None;
+
+                    #[cfg(feature = "libsql")]
+                    let store = store.or_else(|| {
+                        libsql_db.take().map(|db| {
+                            Arc::new(LibSqlSecretsStore::new(db, Arc::clone(&crypto)))
+                                as Arc<dyn SecretsStore + Send + Sync>
+                        })
+                    });
+
+                    #[cfg(feature = "postgres")]
+                    let store = store.or_else(|| {
+                        pg_pool.as_ref().map(|pool| {
+                            Arc::new(PostgresSecretsStore::new(pool.clone(), Arc::clone(&crypto)))
+                                as Arc<dyn SecretsStore + Send + Sync>
+                        })
+                    });
+
+                    store
+                }
+                Err(e) => {
+                    tracing::warn!("Failed to initialize secrets crypto: {}", e);
+                    #[cfg(feature = "libsql")]
+                    let _ = libsql_db.take();
+                    None
+                }
+            }
+        } else {
+            #[cfg(feature = "libsql")]
+            let _ = libsql_db.take();
+            None
+        };
+
     let mcp_session_manager = Arc::new(McpSessionManager::new());
 
     // Create WASM tool runtime (sync, just builds the wasmtime engine)
@@ -649,10 +579,7 @@ async fn main() -> anyhow::Result<()> {
     // Both register into the shared ToolRegistry (RwLock-based) so concurrent writes are safe.
     let wasm_tools_future = async {
         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));
-            }
+            let loader = WasmToolLoader::new(Arc::clone(runtime), Arc::clone(&tools));
 
             // Load installed tools from ~/.ironclaw/tools/
             match loader.load_from_dir(&config.wasm.tools_dir).await {
@@ -898,14 +825,12 @@ async fn main() -> anyhow::Result<()> {
 
     // Initialize channel manager
     let mut channels = ChannelManager::new();
-    let mut channel_names: Vec<String> = Vec::new();
 
     if let Some(repl) = repl_channel {
         channels.add(Box::new(repl));
         if cli.message.is_some() {
             tracing::info!("Single message mode");
         } else {
-            channel_names.push("repl".to_string());
             tracing::info!("REPL mode enabled");
         }
     }
@@ -977,13 +902,13 @@ async fn main() -> anyhow::Result<()> {
 
                                 // Inject owner_id for Telegram so the bot only responds
                                 // to the bound user account.
-                                if channel_name == "telegram"
-                                    && let Some(owner_id) = config.channels.telegram_owner_id
-                                {
-                                    config_updates.insert(
-                                        "owner_id".to_string(),
-                                        serde_json::json!(owner_id),
-                                    );
+                                if channel_name == "telegram" {
+                                    if let Some(owner_id) = config.channels.telegram_owner_id {
+                                        config_updates.insert(
+                                            "owner_id".to_string(),
+                                            serde_json::json!(owner_id),
+                                        );
+                                    }
                                 }
 
                                 if !config_updates.is_empty() {
@@ -1041,7 +966,6 @@ async fn main() -> anyhow::Result<()> {
                                 }
                             }
 
-                            channel_names.push(channel_name.clone());
                             channels.add(Box::new(SharedWasmChannel::new(channel_arc)));
                         }
 
@@ -1075,24 +999,23 @@ async fn main() -> anyhow::Result<()> {
     // Extract its routes for the unified server; the channel itself just
     // provides the mpsc stream.
     let mut webhook_server_addr: Option<std::net::SocketAddr> = None;
-    if !cli.cli_only
-        && let Some(ref http_config) = config.channels.http
-    {
-        let http_channel = HttpChannel::new(http_config.clone());
-        webhook_routes.push(http_channel.routes());
-        let (host, port) = http_channel.addr();
-        webhook_server_addr = Some(
-            format!("{}:{}", host, port)
-                .parse()
-                .expect("HttpConfig host:port must be a valid SocketAddr"),
-        );
-        channel_names.push("http".to_string());
-        channels.add(Box::new(http_channel));
-        tracing::info!(
-            "HTTP channel enabled on {}:{}",
-            http_config.host,
-            http_config.port
-        );
+    if !cli.cli_only {
+        if let Some(ref http_config) = config.channels.http {
+            let http_channel = HttpChannel::new(http_config.clone());
+            webhook_routes.push(http_channel.routes());
+            let (host, port) = http_channel.addr();
+            webhook_server_addr = Some(
+                format!("{}:{}", host, port)
+                    .parse()
+                    .expect("HttpConfig host:port must be a valid SocketAddr"),
+            );
+            channels.add(Box::new(http_channel));
+            tracing::info!(
+                "HTTP channel enabled on {}:{}",
+                http_config.host,
+                http_config.port
+            );
+        }
     }
 
     // Start the unified webhook server if any routes were registered.
@@ -1149,11 +1072,8 @@ async fn main() -> anyhow::Result<()> {
     // Create context manager (shared between job tools and agent)
     let context_manager = Arc::new(ContextManager::new(config.agent.max_parallel_jobs));
 
-    // Create hook registry
-    let hooks = Arc::new(HookRegistry::new());
-
     // Create session manager (shared between agent and web gateway)
-    let session_manager = Arc::new(SessionManager::new().with_hooks(hooks.clone()));
+    let session_manager = Arc::new(SessionManager::new());
 
     // Register job tools (sandbox deps auto-injected when container_job_manager is available)
     tools.register_job_tools(
@@ -1163,7 +1083,6 @@ async fn main() -> anyhow::Result<()> {
     );
 
     // Add web gateway channel if configured
-    let mut gateway_url: Option<String> = None;
     if let Some(ref gw_config) = config.channels.gateway {
         let mut gw = GatewayChannel::new(gw_config.clone());
         if let Some(ref ws) = workspace {
@@ -1196,39 +1115,29 @@ async fn main() -> anyhow::Result<()> {
             }
         }
 
-        gateway_url = Some(format!(
-            "http://{}:{}/?token={}",
-            gw_config.host,
-            gw_config.port,
-            gw.auth_token()
-        ));
-
         tracing::info!(
             "Web gateway enabled on {}:{}",
             gw_config.host,
             gw_config.port
         );
-        tracing::info!("Web UI: http://{}:{}/", gw_config.host, gw_config.port);
+        tracing::info!(
+            "Web UI: http://{}:{}/?token={}",
+            gw_config.host,
+            gw_config.port,
+            gw.auth_token()
+        );
 
-        channel_names.push("gateway".to_string());
         channels.add(Box::new(gw));
     }
 
-    // Capture boot screen info before moving Arcs into AgentDeps.
-    let boot_tool_count = tools.count();
-    let boot_llm_model = llm.model_name().to_string();
-    let boot_cheap_model = cheap_llm.as_ref().map(|c| c.model_name().to_string());
-
     // Create and run the agent
     let deps = AgentDeps {
         store: db,
         llm,
-        cheap_llm,
         safety,
         tools,
         workspace,
         extension_manager,
-        hooks,
     };
     let agent = Agent::new(
         config.agent.clone(),
@@ -1242,38 +1151,6 @@ async fn main() -> anyhow::Result<()> {
 
     tracing::info!("Agent initialized, starting main loop...");
 
-    // Print boot screen for interactive CLI mode (not single-message mode).
-    if config.channels.cli.enabled && cli.message.is_none() {
-        let boot_info = ironclaw::boot_screen::BootInfo {
-            version: env!("CARGO_PKG_VERSION").to_string(),
-            agent_name: config.agent.name.clone(),
-            llm_backend: config.llm.backend.to_string(),
-            llm_model: boot_llm_model,
-            cheap_model: boot_cheap_model,
-            db_backend: if cli.no_db {
-                "none".to_string()
-            } else {
-                config.database.backend.to_string()
-            },
-            db_connected: !cli.no_db,
-            tool_count: boot_tool_count,
-            gateway_url,
-            embeddings_enabled: config.embeddings.enabled,
-            embeddings_provider: if config.embeddings.enabled {
-                Some(config.embeddings.provider.clone())
-            } else {
-                None
-            },
-            heartbeat_enabled: config.heartbeat.enabled,
-            heartbeat_interval_secs: config.heartbeat.interval_secs,
-            sandbox_enabled: config.sandbox.enabled,
-            claude_code_enabled: config.claude_code.enabled,
-            routines_enabled: config.routines.enabled,
-            channels: channel_names,
-        };
-        ironclaw::boot_screen::print_boot_screen(&boot_info);
-    }
-
     // Run the agent (blocks until shutdown)
     agent.run().await?;
 
@@ -1289,11 +1166,13 @@ async fn main() -> anyhow::Result<()> {
 /// Check if onboarding is needed and return the reason.
 ///
 /// Returns `Some(reason)` if onboarding should be triggered, `None` otherwise.
-/// Called after `load_ironclaw_env()`, so DATABASE_URL from `~/.ironclaw/.env`
-/// is already in the environment.
 #[cfg(any(feature = "postgres", feature = "libsql"))]
-fn check_onboard_needed() -> Option<&'static str> {
-    let has_db = std::env::var("DATABASE_URL").is_ok()
+async fn check_onboard_needed() -> Option<&'static str> {
+    let bootstrap = ironclaw::bootstrap::BootstrapConfig::load();
+
+    // Database not configured (and not in env)
+    let has_db = bootstrap.database_url.is_some()
+        || std::env::var("DATABASE_URL").is_ok()
         || std::env::var("LIBSQL_PATH").is_ok()
         || ironclaw::config::default_libsql_path().exists();
 
@@ -1301,16 +1180,19 @@ fn check_onboard_needed() -> Option<&'static str> {
         return Some("Database not configured");
     }
 
-    // First run (onboarding never completed and no session).
-    // Reads NEARAI_API_KEY env var directly because this function runs
-    // before Config is loaded -- Config::from_env() may fail without a
-    // database URL, which is what triggers onboarding in the first place.
-    if std::env::var("NEARAI_API_KEY").is_err() {
-        let settings = ironclaw::settings::Settings::load();
-        let session_path = ironclaw::llm::session::default_session_path();
-        if !settings.onboard_completed && !session_path.exists() {
-            return Some("First run");
-        }
+    // Secrets not configured (and not in env)
+    if bootstrap.secrets_master_key_source == ironclaw::settings::KeySource::None
+        && std::env::var("SECRETS_MASTER_KEY").is_err()
+        && !ironclaw::secrets::keychain::has_master_key().await
+    {
+        // Only require secrets setup if user hasn't explicitly disabled it
+        // For now, we don't require it for first run
+    }
+
+    // First run (onboarding never completed and no session)
+    let session_path = ironclaw::llm::session::default_session_path();
+    if !bootstrap.onboard_completed && !session_path.exists() {
+        return Some("First run");
     }
 
     None

src/orchestrator/api.rs

@@ -202,7 +202,7 @@ async fn report_complete(
     State(state): State<OrchestratorState>,
     Path(job_id): Path<Uuid>,
     Json(report): Json<CompletionReport>,
-) -> Result<Json<serde_json::Value>, StatusCode> {
+) -> Result<StatusCode, StatusCode> {
     if report.success {
         tracing::info!(
             job_id = %job_id,
@@ -223,7 +223,7 @@ async fn report_complete(
     };
     let _ = state.job_manager.complete_job(job_id, result).await;
 
-    Ok(Json(serde_json::json!({"status": "ok"})))
+    Ok(StatusCode::OK)
 }
 
 // -- Sandbox job event handlers --
@@ -339,16 +339,16 @@ async fn get_prompt_handler(
     Path(job_id): Path<Uuid>,
 ) -> Result<(StatusCode, Json<serde_json::Value>), StatusCode> {
     let mut queue = state.prompt_queue.lock().await;
-    if let Some(prompts) = queue.get_mut(&job_id)
-        && let Some(prompt) = prompts.pop_front()
-    {
-        return Ok((
-            StatusCode::OK,
-            Json(serde_json::json!({
-                "content": prompt.content,
-                "done": prompt.done,
-            })),
-        ));
+    if let Some(prompts) = queue.get_mut(&job_id) {
+        if let Some(prompt) = prompts.pop_front() {
+            return Ok((
+                StatusCode::OK,
+                Json(serde_json::json!({
+                    "content": prompt.content,
+                    "done": prompt.done,
+                })),
+            ));
+        }
     }
 
     // Return 204 with an empty body. The Json wrapper requires some value

src/orchestrator/job_manager.rs

@@ -229,17 +229,17 @@ impl ContainerJobManager {
                 .unwrap_or_else(|| PathBuf::from("."))
                 .join(".ironclaw")
                 .join("projects");
-            if let Ok(canonical_base) = projects_base.canonicalize()
-                && !canonical.starts_with(&canonical_base)
-            {
-                return Err(OrchestratorError::ContainerCreationFailed {
-                    job_id,
-                    reason: format!(
-                        "project directory {} is outside allowed base {}",
-                        canonical.display(),
-                        canonical_base.display()
-                    ),
-                });
+            if let Ok(canonical_base) = projects_base.canonicalize() {
+                if !canonical.starts_with(&canonical_base) {
+                    return Err(OrchestratorError::ContainerCreationFailed {
+                        job_id,
+                        reason: format!(
+                            "project directory {} is outside allowed base {}",
+                            canonical.display(),
+                            canonical_base.display()
+                        ),
+                    });
+                }
             }
             binds.push(format!("{}:/workspace:rw", canonical.display()));
             env_vec.push("IRONCLAW_WORKSPACE=/workspace".to_string());
@@ -442,36 +442,36 @@ impl ContainerJobManager {
             let containers = self.containers.read().await;
             containers.get(&job_id).map(|h| h.container_id.clone())
         };
-        if let Some(cid) = container_id
-            && !cid.is_empty()
-        {
-            match connect_docker().await {
-                Ok(docker) => {
-                    if let Err(e) = docker
-                        .stop_container(
-                            &cid,
-                            Some(bollard::container::StopContainerOptions { t: 5 }),
-                        )
-                        .await
-                    {
-                        tracing::warn!(job_id = %job_id, error = %e, "Failed to stop completed container");
+        if let Some(cid) = container_id {
+            if !cid.is_empty() {
+                match connect_docker().await {
+                    Ok(docker) => {
+                        if let Err(e) = docker
+                            .stop_container(
+                                &cid,
+                                Some(bollard::container::StopContainerOptions { t: 5 }),
+                            )
+                            .await
+                        {
+                            tracing::warn!(job_id = %job_id, error = %e, "Failed to stop completed container");
+                        }
+                        if let Err(e) = docker
+                            .remove_container(
+                                &cid,
+                                Some(bollard::container::RemoveContainerOptions {
+                                    force: true,
+                                    ..Default::default()
+                                }),
+                            )
+                            .await
+                        {
+                            tracing::warn!(job_id = %job_id, error = %e, "Failed to remove completed container");
+                        }
                     }
-                    if let Err(e) = docker
-                        .remove_container(
-                            &cid,
-                            Some(bollard::container::RemoveContainerOptions {
-                                force: true,
-                                ..Default::default()
-                            }),
-                        )
-                        .await
-                    {
-                        tracing::warn!(job_id = %job_id, error = %e, "Failed to remove completed container");
+                    Err(e) => {
+                        tracing::warn!(job_id = %job_id, error = %e, "Failed to connect to Docker for container cleanup");
                     }
                 }
-                Err(e) => {
-                    tracing::warn!(job_id = %job_id, error = %e, "Failed to connect to Docker for container cleanup");
-                }
             }
         }
         self.token_store.revoke(job_id).await;

src/safety/leak_detector.rs

@@ -147,10 +147,10 @@ impl LeakDetector {
         // Build prefix matcher for patterns that start with a known prefix
         let mut prefixes = Vec::new();
         for (idx, pattern) in patterns.iter().enumerate() {
-            if let Some(prefix) = extract_literal_prefix(pattern.regex.as_str())
-                && prefix.len() >= 3
-            {
-                prefixes.push((prefix, idx));
+            if let Some(prefix) = extract_literal_prefix(pattern.regex.as_str()) {
+                if prefix.len() >= 3 {
+                    prefixes.push((prefix, idx));
+                }
             }
         }
 

src/sandbox/container.rs

@@ -494,10 +494,10 @@ impl ContainerRunner {
 /// 3. `~/.docker/run/docker.sock` (Docker Desktop on macOS)
 pub async fn connect_docker() -> Result<Docker> {
     // First try bollard defaults (checks DOCKER_HOST, then /var/run/docker.sock)
-    if let Ok(docker) = Docker::connect_with_local_defaults()
-        && docker.ping().await.is_ok()
-    {
-        return Ok(docker);
+    if let Ok(docker) = Docker::connect_with_local_defaults() {
+        if docker.ping().await.is_ok() {
+            return Ok(docker);
+        }
     }
 
     // Try Docker Desktop socket (macOS)
@@ -507,9 +507,10 @@ pub async fn connect_docker() -> Result<Docker> {
             let sock_str = desktop_sock.to_string_lossy();
             if let Ok(docker) =
                 Docker::connect_with_socket(&sock_str, 120, bollard::API_DEFAULT_VERSION)
-                && docker.ping().await.is_ok()
             {
-                return Ok(docker);
+                if docker.ping().await.is_ok() {
+                    return Ok(docker);
+                }
             }
         }
     }

src/sandbox/proxy/http.rs

@@ -259,11 +259,11 @@ async fn handle_connect(
 
     let decision = state.decider.decide(&network_req).await;
 
-    if !decision.is_allowed()
-        && let NetworkDecision::Deny { reason } = decision
-    {
-        tracing::info!("Proxy: blocked CONNECT {} - {}", host, reason);
-        return error_response(StatusCode::FORBIDDEN, reason);
+    if !decision.is_allowed() {
+        if let NetworkDecision::Deny { reason } = decision {
+            tracing::info!("Proxy: blocked CONNECT {} - {}", host, reason);
+            return error_response(StatusCode::FORBIDDEN, reason);
+        }
     }
 
     tracing::debug!("Proxy: allowing CONNECT to {}", host);
@@ -294,10 +294,10 @@ async fn forward_request(
 
     // Copy headers (except hop-by-hop headers)
     for (name, value) in req.headers() {
-        if !is_hop_by_hop_header(name.as_str())
-            && let Ok(v) = value.to_str()
-        {
-            builder = builder.header(name.as_str(), v);
+        if !is_hop_by_hop_header(name.as_str()) {
+            if let Ok(v) = value.to_str() {
+                builder = builder.header(name.as_str(), v);
+            }
         }
     }
 

src/sandbox/proxy/policy.rs

@@ -109,11 +109,12 @@ impl NetworkPolicyDecider for DefaultPolicyDecider {
     async fn decide(&self, request: &NetworkRequest) -> NetworkDecision {
         // First check if the domain is allowed
         let validation = self.allowlist.is_allowed(&request.host);
-        if !validation.is_allowed()
-            && let crate::sandbox::proxy::allowlist::DomainValidationResult::Denied(reason) =
+        if !validation.is_allowed() {
+            if let crate::sandbox::proxy::allowlist::DomainValidationResult::Denied(reason) =
                 validation
-        {
-            return NetworkDecision::Deny { reason };
+            {
+                return NetworkDecision::Deny { reason };
+            }
         }
 
         // Check if we need to inject credentials

src/secrets/keychain.rs

@@ -261,7 +261,7 @@ pub use platform::{delete_master_key, get_master_key, has_master_key, store_mast
 
 /// Parse a hex string to bytes.
 fn hex_to_bytes(hex: &str) -> Result<Vec<u8>, SecretError> {
-    if !hex.len().is_multiple_of(2) {
+    if hex.len() % 2 != 0 {
         return Err(SecretError::KeychainError(
             "Invalid hex string length".to_string(),
         ));

src/secrets/store.rs

@@ -153,10 +153,10 @@ impl SecretsStore for PostgresSecretsStore {
                 let secret = row_to_secret(&r);
 
                 // Check expiration
-                if let Some(expires_at) = secret.expires_at
-                    && expires_at < Utc::now()
-                {
-                    return Err(SecretError::Expired);
+                if let Some(expires_at) = secret.expires_at {
+                    if expires_at < Utc::now() {
+                        return Err(SecretError::Expired);
+                    }
                 }
 
                 Ok(secret)
@@ -276,10 +276,10 @@ impl SecretsStore for PostgresSecretsStore {
             }
 
             // Simple glob: * matches any suffix
-            if let Some(prefix) = pattern.strip_suffix('*')
-                && secret_name.starts_with(prefix)
-            {
-                return Ok(true);
+            if let Some(prefix) = pattern.strip_suffix('*') {
+                if secret_name.starts_with(prefix) {
+                    return Ok(true);
+                }
             }
         }
 
@@ -432,10 +432,10 @@ impl SecretsStore for LibSqlSecretsStore {
             Some(row) => {
                 let secret = libsql_row_to_secret(&row)?;
 
-                if let Some(expires_at) = secret.expires_at
-                    && expires_at < Utc::now()
-                {
-                    return Err(SecretError::Expired);
+                if let Some(expires_at) = secret.expires_at {
+                    if expires_at < Utc::now() {
+                        return Err(SecretError::Expired);
+                    }
                 }
 
                 Ok(secret)
@@ -541,10 +541,10 @@ impl SecretsStore for LibSqlSecretsStore {
                 return Ok(true);
             }
 
-            if let Some(prefix) = pattern.strip_suffix('*')
-                && secret_name.starts_with(prefix)
-            {
-                return Ok(true);
+            if let Some(prefix) = pattern.strip_suffix('*') {
+                if secret_name.starts_with(prefix) {
+                    return Ok(true);
+                }
             }
         }
 
@@ -695,21 +695,12 @@ pub mod testing {
         }
 
         async fn get(&self, user_id: &str, name: &str) -> Result<Secret, SecretError> {
-            let secret = self
-                .secrets
+            self.secrets
                 .read()
                 .await
                 .get(&(user_id.to_string(), name.to_string()))
                 .cloned()
-                .ok_or_else(|| SecretError::NotFound(name.to_string()))?;
-
-            if let Some(expires_at) = secret.expires_at
-                && expires_at < Utc::now()
-            {
-                return Err(SecretError::Expired);
-            }
-
-            Ok(secret)
+                .ok_or_else(|| SecretError::NotFound(name.to_string()))
         }
 
         async fn get_decrypted(
@@ -770,10 +761,10 @@ pub mod testing {
                 if pattern == secret_name {
                     return Ok(true);
                 }
-                if let Some(prefix) = pattern.strip_suffix('*')
-                    && secret_name.starts_with(prefix)
-                {
-                    return Ok(true);
+                if let Some(prefix) = pattern.strip_suffix('*') {
+                    if secret_name.starts_with(prefix) {
+                        return Ok(true);
+                    }
                 }
             }
             Ok(false)
@@ -898,34 +889,6 @@ mod tests {
         );
     }
 
-    #[tokio::test]
-    async fn test_expired_secret_returns_error() {
-        let store = test_store();
-        let expires_at = chrono::Utc::now() - chrono::Duration::hours(1);
-        let params = CreateSecretParams::new("expired_key", "value").with_expiry(expires_at);
-
-        store.create("user1", params).await.unwrap();
-
-        let result = store.get("user1", "expired_key").await;
-        assert!(result.is_err());
-        assert!(matches!(
-            result.unwrap_err(),
-            crate::secrets::SecretError::Expired
-        ));
-    }
-
-    #[tokio::test]
-    async fn test_non_expired_secret_succeeds() {
-        let store = test_store();
-        let expires_at = chrono::Utc::now() + chrono::Duration::hours(1);
-        let params = CreateSecretParams::new("fresh_key", "value").with_expiry(expires_at);
-
-        store.create("user1", params).await.unwrap();
-
-        let result = store.get("user1", "fresh_key").await;
-        assert!(result.is_ok());
-    }
-
     #[tokio::test]
     async fn test_user_isolation() {
         let store = test_store();

src/settings.rs

@@ -40,18 +40,8 @@ pub struct Settings {
     #[serde(default)]
     pub secrets_master_key_source: KeySource,
 
-    // === Step 3: Inference Provider ===
-    /// LLM backend: "nearai", "anthropic", "openai", "ollama", "openai_compatible".
-    #[serde(default)]
-    pub llm_backend: Option<String>,
-
-    /// Ollama base URL (when llm_backend = "ollama").
-    #[serde(default)]
-    pub ollama_base_url: Option<String>,
-
-    /// OpenAI-compatible endpoint base URL (when llm_backend = "openai_compatible").
-    #[serde(default)]
-    pub openai_compatible_base_url: Option<String>,
+    // === Step 3: NEAR AI Auth ===
+    // Session stored separately in session.json
 
     // === Step 4: Model Selection ===
     /// Currently selected model.
@@ -509,16 +499,20 @@ impl Default for BuilderSettings {
 }
 
 impl Settings {
+    /// Get the default settings file path (~/.ironclaw/settings.json).
+    pub fn default_path() -> PathBuf {
+        dirs::home_dir()
+            .unwrap_or_else(|| PathBuf::from("."))
+            .join(".ironclaw")
+            .join("settings.json")
+    }
+
     /// Reconstruct Settings from a flat key-value map (as stored in the DB).
     ///
     /// Each key is a dotted path (e.g., "agent.name"), value is a JSONB value.
     /// Missing keys get their default value.
     pub fn from_db_map(map: &std::collections::HashMap<String, serde_json::Value>) -> Self {
-        // Start with defaults, then overlay each DB setting.
-        //
-        // The settings table stores both Settings struct fields and app-specific
-        // data (e.g. nearai.session_token). Skip keys that don't correspond to
-        // a known Settings path.
+        // Start with defaults, then overlay each DB setting
         let mut settings = Self::default();
 
         for (key, value) in map {
@@ -527,23 +521,17 @@ impl Settings {
                 serde_json::Value::String(s) => s.clone(),
                 serde_json::Value::Bool(b) => b.to_string(),
                 serde_json::Value::Number(n) => n.to_string(),
-                serde_json::Value::Null => continue, // null means default, skip
+                serde_json::Value::Null => "null".to_string(),
                 other => other.to_string(),
             };
 
-            match settings.set(key, &value_str) {
-                Ok(()) => {}
-                // The settings table stores both Settings fields and app-specific
-                // data (e.g. nearai.session_token). Silently skip unknown paths.
-                Err(e) if e.starts_with("Path not found") => {}
-                Err(e) => {
-                    tracing::warn!(
-                        "Failed to apply DB setting '{}' = '{}': {}",
-                        key,
-                        value_str,
-                        e
-                    );
-                }
+            if let Err(e) = settings.set(key, &value_str) {
+                tracing::warn!(
+                    "Failed to apply DB setting '{}' = '{}': {}",
+                    key,
+                    value_str,
+                    e
+                );
             }
         }
 
@@ -564,27 +552,50 @@ impl Settings {
         map
     }
 
-    /// Get the default settings file path (~/.ironclaw/settings.json).
-    pub fn default_path() -> std::path::PathBuf {
-        dirs::home_dir()
-            .unwrap_or_else(|| std::path::PathBuf::from("."))
-            .join(".ironclaw")
-            .join("settings.json")
-    }
-
     /// Load settings from disk, returning default if not found.
     pub fn load() -> Self {
         Self::load_from(&Self::default_path())
     }
 
-    /// Load settings from a specific path (used by bootstrap legacy migration).
-    pub fn load_from(path: &std::path::Path) -> Self {
+    /// Load settings from a specific path.
+    pub fn load_from(path: &PathBuf) -> Self {
         match std::fs::read_to_string(path) {
             Ok(data) => serde_json::from_str(&data).unwrap_or_default(),
             Err(_) => Self::default(),
         }
     }
 
+    /// Save settings to disk.
+    pub fn save(&self) -> std::io::Result<()> {
+        self.save_to(&Self::default_path())
+    }
+
+    /// Save settings to a specific path.
+    pub fn save_to(&self, path: &PathBuf) -> std::io::Result<()> {
+        // Ensure parent directory exists
+        if let Some(parent) = path.parent() {
+            std::fs::create_dir_all(parent)?;
+        }
+
+        let json = serde_json::to_string_pretty(self)
+            .map_err(|e| std::io::Error::new(std::io::ErrorKind::InvalidData, e.to_string()))?;
+
+        std::fs::write(path, json)
+    }
+
+    /// Get the selected model, falling back to the provided default.
+    pub fn model_or(&self, default: &str) -> String {
+        self.selected_model
+            .clone()
+            .unwrap_or_else(|| default.to_string())
+    }
+
+    /// Set the selected model and save.
+    pub fn set_model(&mut self, model: &str) -> std::io::Result<()> {
+        self.selected_model = Some(model.to_string());
+        self.save()
+    }
+
     /// Get a setting value by dotted path (e.g., "agent.max_parallel_jobs").
     pub fn get(&self, path: &str) -> Option<String> {
         let json = serde_json::to_value(self).ok()?;
@@ -769,22 +780,42 @@ fn collect_settings(
 #[cfg(test)]
 mod tests {
     use super::*;
+    use tempfile::tempdir;
 
     #[test]
-    fn test_db_map_round_trip() {
+    fn test_settings_save_load() {
+        let dir = tempdir().unwrap();
+        let path = dir.path().join("settings.json");
+
         let settings = Settings {
             selected_model: Some("claude-3-5-sonnet-20241022".to_string()),
             ..Default::default()
         };
 
-        let map = settings.to_db_map();
-        let restored = Settings::from_db_map(&map);
+        settings.save_to(&path).unwrap();
+
+        let loaded = Settings::load_from(&path);
         assert_eq!(
-            restored.selected_model,
+            loaded.selected_model,
             Some("claude-3-5-sonnet-20241022".to_string())
         );
     }
 
+    #[test]
+    fn test_model_or_default() {
+        let settings = Settings::default();
+        assert_eq!(
+            settings.model_or("default-model"),
+            "default-model".to_string()
+        );
+
+        let settings = Settings {
+            selected_model: Some("my-model".to_string()),
+            ..Default::default()
+        };
+        assert_eq!(settings.model_or("default-model"), "my-model".to_string());
+    }
+
     #[test]
     fn test_get_setting() {
         let settings = Settings::default();
@@ -855,13 +886,16 @@ mod tests {
     }
 
     #[test]
-    fn test_telegram_owner_id_db_round_trip() {
+    fn test_telegram_owner_id_round_trip() {
+        let dir = tempdir().unwrap();
+        let path = dir.path().join("settings.json");
+
         let mut settings = Settings::default();
         settings.channels.telegram_owner_id = Some(123456789);
+        settings.save_to(&path).unwrap();
 
-        let map = settings.to_db_map();
-        let restored = Settings::from_db_map(&map);
-        assert_eq!(restored.channels.telegram_owner_id, Some(123456789));
+        let loaded = Settings::load_from(&path);
+        assert_eq!(loaded.channels.telegram_owner_id, Some(123456789));
     }
 
     #[test]
@@ -878,30 +912,4 @@ mod tests {
             .unwrap();
         assert_eq!(settings.channels.telegram_owner_id, Some(987654321));
     }
-
-    #[test]
-    fn test_llm_backend_round_trip() {
-        let dir = tempfile::tempdir().unwrap();
-        let path = dir.path().join("settings.json");
-
-        let settings = Settings {
-            llm_backend: Some("anthropic".to_string()),
-            ollama_base_url: Some("http://localhost:11434".to_string()),
-            openai_compatible_base_url: Some("http://my-vllm:8000/v1".to_string()),
-            ..Default::default()
-        };
-        let json = serde_json::to_string_pretty(&settings).unwrap();
-        std::fs::write(&path, json).unwrap();
-
-        let loaded = Settings::load_from(&path);
-        assert_eq!(loaded.llm_backend, Some("anthropic".to_string()));
-        assert_eq!(
-            loaded.ollama_base_url,
-            Some("http://localhost:11434".to_string())
-        );
-        assert_eq!(
-            loaded.openai_compatible_base_url,
-            Some("http://my-vllm:8000/v1".to_string())
-        );
-    }
 }

src/setup/README.md

@@ -1,539 +0,0 @@
-# Setup / Onboarding Specification
-
-This document is the authoritative specification for IronClaw's onboarding
-wizard. Any code change to `src/setup/` **must** keep this document in sync.
-If a future contributor or coding agent modifies setup behavior, update this
-file first, then adjust the code to match.
-
----
-
-## Entry Points
-
-```
-ironclaw onboard [--skip-auth] [--channels-only]
-```
-
-Explicit invocation. Loads `.env` files, runs the wizard, exits.
-
-```
-ironclaw          (first run, no database configured)
-```
-
-Auto-detection via `check_onboard_needed()` in `main.rs`. Triggers when
-none of these are true:
-- `DATABASE_URL` env var is set
-- `LIBSQL_PATH` env var is set
-- `~/.ironclaw/ironclaw.db` exists on disk
-
-The `--no-onboard` CLI flag suppresses auto-detection.
-
----
-
-## Startup Sequence (main.rs)
-
-```
-1. Parse CLI args
-2. If Command::Onboard  → load .env, run wizard, exit
-3. If Command::Run or no command:
-   a. Load .env files (dotenvy::dotenv() then load_ironclaw_env())
-   b. check_onboard_needed() → run wizard if needed
-   c. Config::from_env()     → build config from env vars
-   d. Create SessionManager  → load session token
-   e. ensure_authenticated() → validate session (NEAR AI only)
-   f. ... rest of agent startup
-```
-
-**Critical ordering:** `.env` files must be loaded (step 3a) before
-`Config::from_env()` (step 3c) because bootstrap vars like
-`DATABASE_BACKEND` live in `~/.ironclaw/.env`.
-
----
-
-## The 7-Step Wizard
-
-### Overview
-
-```
-Step 1: Database Connection
-Step 2: Security (master key)
-Step 3: Inference Provider          ← skipped if --skip-auth
-Step 4: Model Selection
-Step 5: Embeddings
-Step 6: Channel Configuration
-Step 7: Background Tasks (heartbeat)
-       ↓
-   save_and_summarize()
-```
-
-`--channels-only` mode runs only Step 6, skipping everything else.
-
----
-
-### Step 1: Database Connection
-
-**Module:** `wizard.rs` → `step_database()`
-
-**Goal:** Select backend, establish connection, run migrations.
-
-**Decision tree:**
-
-```
-Both features compiled?
-├─ Yes → DATABASE_BACKEND env var set?
-│  ├─ Yes → use that backend
-│  └─ No  → interactive selection (PostgreSQL vs libSQL)
-├─ Only postgres feature → step_database_postgres()
-└─ Only libsql feature  → step_database_libsql()
-```
-
-**PostgreSQL path** (`step_database_postgres`):
-1. Check `DATABASE_URL` from env or settings
-2. Test connection (creates `deadpool_postgres::Pool`)
-3. Optionally run refinery migrations
-4. Store pool in `self.db_pool`
-
-**libSQL path** (`step_database_libsql`):
-1. Offer local path (default: `~/.ironclaw/ironclaw.db`)
-2. Optional Turso cloud sync (URL + auth token)
-3. Test connection (creates `LibSqlBackend`)
-4. Always run migrations (idempotent CREATE IF NOT EXISTS)
-5. Store backend in `self.db_backend`
-
-**Invariant:** After Step 1, exactly one of `self.db_pool` or
-`self.db_backend` is `Some`. This is required for settings persistence
-in `save_and_summarize()`.
-
----
-
-### Step 2: Security (Master Key)
-
-**Module:** `wizard.rs` → `step_security()`
-
-**Goal:** Configure encryption for API tokens and secrets.
-
-**Decision tree:**
-
-```
-SECRETS_MASTER_KEY env var set?
-├─ Yes → use env var, done
-└─ No  → try get_master_key() from OS keychain
-   ├─ Ok(bytes) → cache in self.secrets_crypto, ask "use existing?"
-   │  ├─ Yes → done (keychain)
-   │  └─ No  → clear cache, fall through to options
-   └─ Err   → fall through to options
-              ├─ OS Keychain: generate + store + build SecretsCrypto
-              ├─ Env variable: generate + print export command
-              └─ Skip: disable secrets features
-```
-
-**CRITICAL CAVEAT: macOS Keychain Dialogs**
-
-On macOS, `security_framework::get_generic_password()` can trigger TWO
-system dialogs:
-1. "Enter your password to unlock the keychain" (keychain locked)
-2. "Allow ironclaw to access this keychain item" (per-app authorization)
-
-This is OS-level behavior we cannot prevent. To minimize pain:
-
-- **Use `get_master_key()` not `has_master_key()`** in step 2. Both call
-  the same underlying API, but `get_master_key()` returns the key bytes
-  so we can cache them. `has_master_key()` throws them away, forcing a
-  second keychain access later.
-
-- **Build `SecretsCrypto` eagerly.** When the keychain key is retrieved,
-  immediately construct `SecretsCrypto` and store in `self.secrets_crypto`.
-  Later calls to `init_secrets_context()` check this field first, avoiding
-  redundant keychain probes.
-
-- **Never probe the keychain in read-only commands** (e.g., `ironclaw status`).
-  The status command reports "env not set (keychain may be configured)"
-  rather than triggering system dialogs.
-
-**Invariant:** After Step 2, `self.secrets_crypto` is `Some` if the user
-chose Keychain or generated a new key. It may be `None` if the user chose
-env-var mode or skipped secrets.
-
----
-
-### Step 3: Inference Provider
-
-**Module:** `wizard.rs` → `step_inference_provider()`
-
-**Goal:** Choose LLM backend and authenticate.
-
-**Providers:**
-
-| Provider | Auth Method | Secret Name | Env Var |
-|----------|-------------|-------------|---------|
-| NEAR AI | Browser OAuth | (session token) | `NEARAI_SESSION_TOKEN` |
-| Anthropic | API key | `anthropic_api_key` | `ANTHROPIC_API_KEY` |
-| OpenAI | API key | `openai_api_key` | `OPENAI_API_KEY` |
-| Ollama | None | - | - |
-| OpenAI-compatible | Optional API key | `llm_compatible_api_key` | `LLM_API_KEY` |
-
-**API-key providers** (`setup_api_key_provider`):
-1. Check env var → if set, ask to reuse, persist to secrets store
-2. Otherwise prompt for key entry via `secret_input()`
-3. Store encrypted in secrets via `init_secrets_context()`
-4. **Cache key in `self.llm_api_key`** for model fetching in Step 4
-
-**NEAR AI** (`setup_nearai`):
-- Calls `session_manager.ensure_authenticated()` which opens browser
-- Session token saved to `~/.ironclaw/session.json`
-
-**`self.llm_api_key` caching:** The wizard caches the API key as
-`Option<SecretString>` so that Step 4 (model fetching) and Step 5
-(embeddings) can use it without re-reading from the secrets store or
-mutating environment variables.
-
----
-
-### Step 4: Model Selection
-
-**Module:** `wizard.rs` → `step_model_selection()`
-
-**Goal:** Choose which model to use.
-
-**Flow:**
-1. If model already set → offer to keep it
-2. Fetch models from provider API (5-second timeout)
-3. On timeout or error → use static fallback list
-4. Present list + "Custom model ID" escape hatch
-5. Store in `self.settings.selected_model`
-
-**Model fetchers pass the cached API key explicitly:**
-```rust
-let cached = self.llm_api_key.as_ref().map(|k| k.expose_secret().to_string());
-let models = fetch_anthropic_models(cached.as_deref()).await;
-```
-
-This avoids mutating environment variables. The fetcher checks the explicit
-key first, then falls back to the standard env var.
-
----
-
-### Step 5: Embeddings
-
-**Module:** `wizard.rs` → `step_embeddings()`
-
-**Goal:** Configure semantic search for workspace memory.
-
-**Flow:**
-1. Ask "Enable semantic search?" (default: yes)
-2. Detect available providers:
-   - NEAR AI: if backend is `nearai` OR valid session exists
-   - OpenAI: if `OPENAI_API_KEY` in env OR (backend is `openai` AND cached key)
-3. If both available → let user choose
-4. If only one → use it
-5. If neither → disable embeddings
-
-**Default model:** `text-embedding-3-small` (for both providers)
-
----
-
-### Step 6: Channel Configuration
-
-**Module:** `wizard.rs` → `step_channels()`, delegating to `channels.rs`
-
-**Goal:** Enable input channels (TUI, HTTP, Telegram, etc.).
-
-**Sub-steps:**
-
-```
-6a. Tunnel setup (if webhook channels needed)
-6b. Discover WASM channels from ~/.ironclaw/channels/
-6c. Multi-select: CLI/TUI, HTTP, discovered channels, bundled channels
-6d. Install missing bundled channels (copy WASM binaries)
-6e. Initialize SecretsContext (for token storage)
-6f. Setup HTTP webhook (if selected)
-6g. Setup each WASM channel (secrets, owner binding)
-```
-
-**Tunnel setup** (`setup_tunnel`):
-- Options: ngrok, Cloudflare Tunnel, localtunnel, custom URL
-- Validates HTTPS requirement
-- Stored in `self.settings.tunnel.public_url`
-
-**WASM channel setup** (`setup_wasm_channel`):
-- Reads `capabilities.json` for `setup.required_secrets`
-- For each secret: check existing, prompt or auto-generate, validate regex
-- Save each secret via `SecretsContext`
-
-**Telegram special case** (`setup_telegram`):
-- Validates bot token via Telegram `getMe` API
-- Owner binding: polls `getUpdates` for 120s to capture sender's user ID
-- Optional webhook secret generation
-
-**SecretsContext creation** (`init_secrets_context`):
-1. Check `self.secrets_crypto` (set in Step 2) → use if available
-2. Else try `SECRETS_MASTER_KEY` env var
-3. Else try `get_master_key()` from keychain (only in `channels_only` mode)
-4. Create backend-appropriate secrets store (respects selected database backend)
-
----
-
-### Step 7: Heartbeat
-
-**Module:** `wizard.rs` → `step_heartbeat()`
-
-**Goal:** Configure periodic background execution.
-
-**Flow:**
-1. Ask "Enable heartbeat?" (default: no)
-2. If yes: interval in minutes (default: 30), notification channel
-3. Store in `self.settings.heartbeat`
-
----
-
-## Settings Persistence
-
-### Two-Layer Architecture
-
-Settings are persisted in two places:
-
-**Layer 1: `~/.ironclaw/.env`** (bootstrap vars)
-
-Contains only the settings needed BEFORE database connection. Written by
-`save_bootstrap_env()` in `bootstrap.rs`.
-
-```env
-DATABASE_BACKEND="libsql"
-LIBSQL_PATH="/Users/name/.ironclaw/ironclaw.db"
-```
-
-Or for PostgreSQL:
-```env
-DATABASE_BACKEND="postgres"
-DATABASE_URL="postgres://user:pass@localhost/ironclaw"
-```
-
-**Why separate?** Chicken-and-egg: you need `DATABASE_BACKEND` to know
-which database to connect to, so it can't be stored in the database.
-
-**Layer 2: Database settings table** (everything else)
-
-All other settings are stored as key-value pairs in the `settings` table,
-keyed by `(user_id, key)`. Written by `set_all_settings()`.
-
-Settings are serialized via `Settings::to_db_map()` as dotted paths:
-```
-database_backend = "libsql"
-llm_backend = "nearai"
-selected_model = "anthropic/claude-sonnet-4-5"
-embeddings.enabled = "true"
-embeddings.provider = "nearai"
-channels.http_enabled = "true"
-heartbeat.enabled = "true"
-heartbeat.interval_secs = "300"
-```
-
-### save_and_summarize()
-
-Final step of the wizard:
-
-```
-1. Mark onboard_completed = true
-2. Write ALL settings to database (try postgres pool, then libSQL backend)
-3. Write bootstrap vars to ~/.ironclaw/.env:
-   - DATABASE_BACKEND (always)
-   - DATABASE_URL     (if postgres)
-   - LIBSQL_PATH      (if libsql)
-   - LIBSQL_URL       (if turso sync)
-4. Print configuration summary
-```
-
-**Invariant:** Both Layer 1 and Layer 2 must be written. If the database
-write fails, the wizard returns an error and the `.env` file is not written.
-
-### Legacy Migration
-
-`bootstrap.rs` handles one-time upgrades from older config formats:
-- `bootstrap.json` → extracts `DATABASE_URL`, writes `.env`, renames to `.migrated`
-- `settings.json` → migrated to database via `migrate_disk_to_db()`
-
----
-
-## Settings Struct
-
-**Module:** `settings.rs`
-
-```rust
-pub struct Settings {
-    // Meta
-    pub onboard_completed: bool,
-
-    // Step 1: Database
-    pub database_backend: Option<String>,    // "postgres" | "libsql"
-    pub database_url: Option<String>,
-    pub libsql_path: Option<String>,
-    pub libsql_url: Option<String>,
-
-    // Step 2: Security
-    pub secrets_master_key_source: KeySource, // Keychain | Env | None
-
-    // Step 3: Inference
-    pub llm_backend: Option<String>,         // "nearai" | "anthropic" | "openai" | "ollama" | "openai_compatible"
-    pub ollama_base_url: Option<String>,
-    pub openai_compatible_base_url: Option<String>,
-
-    // Step 4: Model
-    pub selected_model: Option<String>,
-
-    // Step 5: Embeddings
-    pub embeddings: EmbeddingsSettings,      // enabled, provider, model
-
-    // Step 6: Channels
-    pub tunnel: TunnelSettings,              // provider, public_url
-    pub channels: ChannelSettings,           // http config, telegram owner, etc.
-
-    // Step 7: Heartbeat
-    pub heartbeat: HeartbeatSettings,        // enabled, interval, notify
-
-    // Advanced (not in wizard, set via `ironclaw config set`)
-    pub agent: AgentSettings,
-    pub wasm: WasmSettings,
-    pub sandbox: SandboxSettings,
-    pub safety: SafetySettings,
-    pub builder: BuilderSettings,
-}
-```
-
-**KeySource enum:** `Keychain | Env | None`
-
----
-
-## Secrets Flow
-
-### SecretsContext
-
-Thin wrapper for setup-time secret operations:
-
-```rust
-pub struct SecretsContext {
-    store: Arc<dyn SecretsStore>,
-    user_id: String,
-}
-```
-
-Created by `init_secrets_context()` which:
-1. Gets `SecretsCrypto` from `self.secrets_crypto` or loads from keychain/env
-2. Creates the appropriate backend store:
-   - If both features compiled: respects `self.settings.database_backend`
-   - Tries selected backend first, falls back to the other
-3. Returns `SecretsContext` wrapping the store
-
-### Secret Storage
-
-Secrets are encrypted with AES-256-GCM using the master key, then stored
-in the database `secrets` table. The wizard writes secrets like:
-
-```
-telegram_bot_token    → encrypted bot token
-telegram_webhook_secret → encrypted webhook HMAC secret
-anthropic_api_key     → encrypted API key
-```
-
----
-
-## Prompt Utilities
-
-**Module:** `prompts.rs`
-
-| Function | Description |
-|----------|-------------|
-| `select_one(label, options)` | Numbered single-choice menu |
-| `select_many(label, options, defaults)` | Checkbox multi-select (raw terminal mode) |
-| `input(label)` | Single line text input |
-| `optional_input(label, hint)` | Text input that can be empty |
-| `secret_input(label)` | Hidden input (shows `*` per char), returns `SecretString` |
-| `confirm(label, default)` | `[Y/n]` or `[y/N]` prompt |
-| `print_header(text)` | Bold section header with underline |
-| `print_step(n, total, text)` | `[1/7] Step Name` |
-| `print_success(text)` | Green checkmark prefix |
-| `print_error(text)` | Red X prefix |
-| `print_info(text)` | Blue info prefix |
-
-`select_many` uses `crossterm` raw mode for arrow key navigation.
-Must properly restore terminal state on all exit paths.
-
----
-
-## Platform Caveats
-
-### macOS Keychain
-
-- `get_generic_password()` triggers system dialogs (unlock + authorize)
-- Two dialogs per call is normal, not a bug
-- Cache the result after first access to avoid repeat prompts
-- Never probe keychain in read-only commands (`status`, `--help`)
-- Service name: `"ironclaw"`, account: `"master_key"`
-
-### Linux Secret Service
-
-- Uses GNOME Keyring or KWallet via `secret-service` crate
-- May need `gnome-keyring` daemon running
-- Collection unlock may prompt for password
-
-### URL Passwords
-
-- `#` is common in URL-encoded passwords (`%23` decoded)
-- `.env` values must be double-quoted to preserve `#`
-- Display masked: `postgres://user:****@host/db`
-
-### Telegram API
-
-- Bot token format: `123456:ABC-DEF...`
-- Token goes in URL path: `https://api.telegram.org/bot{TOKEN}/method`
-- Webhook secret header: `X-Telegram-Bot-Api-Secret-Token`
-- Owner binding polls `getUpdates` (must delete webhook first)
-
----
-
-## Testing
-
-Tests live in `mod tests {}` at the bottom of each file.
-
-**What to test when modifying setup:**
-
-- Settings round-trip: `to_db_map()` then `from_db_map()` preserves values
-- Bootstrap `.env`: dotenvy can parse what `save_bootstrap_env()` writes
-- Model fetchers: static fallback works when API is unreachable
-- Channel discovery: handles missing dir, invalid JSON, deduplication
-- Prompt functions: not tested (interactive I/O), but ensure error paths
-  don't panic
-
-**Run setup tests:**
-```bash
-cargo test --lib -- setup
-cargo test --lib -- bootstrap
-```
-
----
-
-## Modification Checklist
-
-When changing the onboarding flow:
-
-1. Update this README first with the intended behavior change
-2. If adding a new wizard step:
-   - Add to the step enum in `run()`, adjust `total_steps`
-   - Add corresponding settings fields to `Settings`
-   - Add `to_db_map` / `from_db_map` serialization
-   - If the setting is needed before DB connection, add to `save_bootstrap_env()`
-3. If adding a new provider or channel:
-   - Add to the selection menu in the appropriate step
-   - Add authentication flow (API key or OAuth)
-   - Add model fetcher with static fallback + 5s timeout
-4. If touching keychain:
-   - Cache the result, never call `get_master_key()` twice
-   - Test on macOS (dialog behavior differs from Linux)
-5. If touching secrets:
-   - Ensure `init_secrets_context()` respects the selected database backend
-   - Test with both postgres and libsql features
-6. Run the full shipping checklist:
-   ```bash
-   cargo fmt
-   cargo clippy --all --benches --tests --examples --all-features -- -D warnings
-   cargo test --lib -- setup bootstrap
-   ```
-7. Test a fresh onboarding: `rm -rf ~/.ironclaw && cargo run`

src/setup/channels.rs

@@ -15,27 +15,11 @@ use serde::Deserialize;
 #[cfg(feature = "postgres")]
 use crate::secrets::SecretsCrypto;
 use crate::secrets::{CreateSecretParams, SecretsStore};
-use crate::settings::{Settings, TunnelSettings};
+use crate::settings::Settings;
 use crate::setup::prompts::{
     confirm, input, optional_input, print_error, print_info, print_success, secret_input,
 };
 
-/// Typed errors for channel setup flows.
-#[derive(Debug, thiserror::Error)]
-pub enum ChannelSetupError {
-    #[error("I/O error: {0}")]
-    Io(#[from] std::io::Error),
-
-    #[error("{0}")]
-    Network(String),
-
-    #[error("{0}")]
-    Secrets(String),
-
-    #[error("{0}")]
-    Validation(String),
-}
-
 /// Context for saving secrets during setup.
 pub struct SecretsContext {
     store: Arc<dyn SecretsStore>,
@@ -61,39 +45,32 @@ impl SecretsContext {
     }
 
     /// Save a secret to the database.
-    pub async fn save_secret(
-        &self,
-        name: &str,
-        value: &SecretString,
-    ) -> Result<(), ChannelSetupError> {
+    pub async fn save_secret(&self, name: &str, value: &SecretString) -> Result<(), String> {
         let params = CreateSecretParams::new(name, value.expose_secret());
 
         self.store
             .create(&self.user_id, params)
             .await
-            .map_err(|e| ChannelSetupError::Secrets(format!("Failed to save secret: {}", e)))?;
+            .map_err(|e| format!("Failed to save secret: {}", e))?;
 
         Ok(())
     }
 
     /// Check if a secret exists.
     pub async fn secret_exists(&self, name: &str) -> bool {
-        match self.store.exists(&self.user_id, name).await {
-            Ok(exists) => exists,
-            Err(e) => {
-                tracing::warn!(secret = name, error = %e, "Failed to check if secret exists, assuming absent");
-                false
-            }
-        }
+        self.store
+            .exists(&self.user_id, name)
+            .await
+            .unwrap_or(false)
     }
 
     /// Read a secret from the database (decrypted).
-    pub async fn get_secret(&self, name: &str) -> Result<SecretString, ChannelSetupError> {
+    pub async fn get_secret(&self, name: &str) -> Result<SecretString, String> {
         let decrypted = self
             .store
             .get_decrypted(&self.user_id, name)
             .await
-            .map_err(|e| ChannelSetupError::Secrets(format!("Failed to read secret: {}", e)))?;
+            .map_err(|e| format!("Failed to read secret: {}", e))?;
         Ok(SecretString::from(decrypted.expose().to_string()))
     }
 }
@@ -130,6 +107,7 @@ struct TelegramGetUpdatesResponse {
 
 #[derive(Debug, Deserialize)]
 struct TelegramUpdate {
+    #[allow(dead_code)]
     update_id: i64,
     message: Option<TelegramUpdateMessage>,
 }
@@ -153,10 +131,7 @@ struct TelegramUpdateUser {
 /// 2. Entering the bot token
 /// 3. Validating the token
 /// 4. Saving the token to the database
-pub async fn setup_telegram(
-    secrets: &SecretsContext,
-    settings: &Settings,
-) -> Result<TelegramSetupResult, ChannelSetupError> {
+pub async fn setup_telegram(secrets: &SecretsContext) -> Result<TelegramSetupResult, String> {
     println!("Telegram Setup:");
     println!();
     print_info("To create a Telegram bot:");
@@ -168,10 +143,10 @@ pub async fn setup_telegram(
     // Check if token already exists
     if secrets.secret_exists("telegram_bot_token").await {
         print_info("Existing Telegram token found in database.");
-        if !confirm("Replace existing token?", false)? {
+        if !confirm("Replace existing token?", false).map_err(|e| e.to_string())? {
             // Still offer to configure webhook secret and owner binding
-            let webhook_secret = setup_telegram_webhook_secret(secrets, &settings.tunnel).await?;
-            let owner_id = bind_telegram_owner_flow(secrets, settings).await?;
+            let webhook_secret = setup_telegram_webhook_secret(secrets).await?;
+            let owner_id = bind_telegram_owner_flow(secrets).await?;
             return Ok(TelegramSetupResult {
                 enabled: true,
                 bot_username: None,
@@ -181,48 +156,47 @@ pub async fn setup_telegram(
         }
     }
 
-    loop {
-        let token = secret_input("Bot token (from @BotFather)")?;
+    let token = secret_input("Bot token (from @BotFather)").map_err(|e| e.to_string())?;
 
-        // Validate the token
-        print_info("Validating bot token...");
+    // Validate the token
+    print_info("Validating bot token...");
 
-        match validate_telegram_token(&token).await {
-            Ok(username) => {
-                print_success(&format!(
-                    "Bot validated: @{}",
-                    username.as_deref().unwrap_or("unknown")
-                ));
+    match validate_telegram_token(&token).await {
+        Ok(username) => {
+            print_success(&format!(
+                "Bot validated: @{}",
+                username.as_deref().unwrap_or("unknown")
+            ));
 
-                // Save to database
-                secrets.save_secret("telegram_bot_token", &token).await?;
-                print_success("Token saved to database");
+            // Save to database
+            secrets.save_secret("telegram_bot_token", &token).await?;
+            print_success("Token saved to database");
 
-                // Bind bot to owner's Telegram account
-                let owner_id = bind_telegram_owner(&token).await?;
+            // Bind bot to owner's Telegram account
+            let owner_id = bind_telegram_owner(&token).await?;
 
-                // Offer webhook secret configuration
-                let webhook_secret =
-                    setup_telegram_webhook_secret(secrets, &settings.tunnel).await?;
+            // Offer webhook secret configuration
+            let webhook_secret = setup_telegram_webhook_secret(secrets).await?;
 
-                return Ok(TelegramSetupResult {
-                    enabled: true,
-                    bot_username: username,
-                    webhook_secret,
-                    owner_id,
-                });
-            }
-            Err(e) => {
-                print_error(&format!("Token validation failed: {}", e));
+            Ok(TelegramSetupResult {
+                enabled: true,
+                bot_username: username,
+                webhook_secret,
+                owner_id,
+            })
+        }
+        Err(e) => {
+            print_error(&format!("Token validation failed: {}", e));
 
-                if !confirm("Try again?", true)? {
-                    return Ok(TelegramSetupResult {
-                        enabled: false,
-                        bot_username: None,
-                        webhook_secret: None,
-                        owner_id: None,
-                    });
-                }
+            if confirm("Try again?", true).map_err(|e| e.to_string())? {
+                Box::pin(setup_telegram(secrets)).await
+            } else {
+                Ok(TelegramSetupResult {
+                    enabled: false,
+                    bot_username: None,
+                    webhook_secret: None,
+                    owner_id: None,
+                })
             }
         }
     }
@@ -232,14 +206,14 @@ pub async fn setup_telegram(
 ///
 /// Polls `getUpdates` until a message arrives, then captures the sender's user ID.
 /// Returns `None` if the user declines or the flow times out.
-async fn bind_telegram_owner(token: &SecretString) -> Result<Option<i64>, ChannelSetupError> {
+async fn bind_telegram_owner(token: &SecretString) -> Result<Option<i64>, String> {
     println!();
     print_info("Account Binding (recommended):");
     print_info("Binding restricts the bot so only YOU can use it.");
     print_info("Without this, anyone who finds your bot can send it messages.");
     println!();
 
-    if !confirm("Bind bot to your Telegram account?", true)? {
+    if !confirm("Bind bot to your Telegram account?", true).map_err(|e| e.to_string())? {
         print_info("Skipping account binding. Bot will accept messages from all users.");
         return Ok(None);
     }
@@ -250,16 +224,14 @@ async fn bind_telegram_owner(token: &SecretString) -> Result<Option<i64>, Channe
     let client = Client::builder()
         .timeout(std::time::Duration::from_secs(35))
         .build()
-        .map_err(|e| ChannelSetupError::Network(format!("Failed to create HTTP client: {}", e)))?;
+        .map_err(|e| format!("Failed to create HTTP client: {}", e))?;
 
     // Clear any existing webhook so getUpdates works
     let delete_url = format!(
         "https://api.telegram.org/bot{}/deleteWebhook",
         token.expose_secret()
     );
-    if let Err(e) = client.post(&delete_url).send().await {
-        tracing::warn!("Failed to delete webhook (getUpdates may not work): {e}");
-    }
+    let _ = client.post(&delete_url).send().await;
 
     let updates_url = format!(
         "https://api.telegram.org/bot{}/getUpdates",
@@ -274,56 +246,49 @@ async fn bind_telegram_owner(token: &SecretString) -> Result<Option<i64>, Channe
             .query(&[("timeout", "30"), ("allowed_updates", "[\"message\"]")])
             .send()
             .await
-            .map_err(|e| ChannelSetupError::Network(format!("getUpdates request failed: {}", e)))?;
+            .map_err(|e| format!("getUpdates request failed: {}", e))?;
 
         if !response.status().is_success() {
-            return Err(ChannelSetupError::Network(format!(
-                "getUpdates returned status {}",
-                response.status()
-            )));
+            return Err(format!("getUpdates returned status {}", response.status()));
         }
 
-        let body: TelegramGetUpdatesResponse = response.json().await.map_err(|e| {
-            ChannelSetupError::Network(format!("Failed to parse getUpdates response: {}", e))
-        })?;
+        let body: TelegramGetUpdatesResponse = response
+            .json()
+            .await
+            .map_err(|e| format!("Failed to parse getUpdates response: {}", e))?;
 
         if !body.ok {
-            return Err(ChannelSetupError::Network(
-                "Telegram API returned error for getUpdates".to_string(),
-            ));
+            return Err("Telegram API returned error for getUpdates".to_string());
         }
 
         // Find the first message with a sender
         for update in &body.result {
-            if let Some(ref msg) = update.message
-                && let Some(ref from) = msg.from
-            {
-                let display_name = from
-                    .username
-                    .as_ref()
-                    .map(|u| format!("@{}", u))
-                    .unwrap_or_else(|| from.first_name.clone());
+            if let Some(ref msg) = update.message {
+                if let Some(ref from) = msg.from {
+                    let display_name = from
+                        .username
+                        .as_ref()
+                        .map(|u| format!("@{}", u))
+                        .unwrap_or_else(|| from.first_name.clone());
 
-                print_success(&format!(
-                    "Received message from {} (ID: {})",
-                    display_name, from.id
-                ));
+                    print_success(&format!(
+                        "Received message from {} (ID: {})",
+                        display_name, from.id
+                    ));
 
-                // Acknowledge the update so it doesn't pile up
-                let ack_url = format!(
-                    "https://api.telegram.org/bot{}/getUpdates",
-                    token.expose_secret()
-                );
-                if let Err(e) = client
-                    .get(&ack_url)
-                    .query(&[("offset", &(update.update_id + 1).to_string())])
-                    .send()
-                    .await
-                {
-                    tracing::warn!("Failed to acknowledge Telegram update: {e}");
+                    // Acknowledge the update so it doesn't pile up
+                    let ack_url = format!(
+                        "https://api.telegram.org/bot{}/getUpdates",
+                        token.expose_secret()
+                    );
+                    let _ = client
+                        .get(&ack_url)
+                        .query(&[("offset", &(update.update_id + 1).to_string())])
+                        .send()
+                        .await;
+
+                    return Ok(Some(from.id));
                 }
-
-                return Ok(Some(from.id));
             }
         }
     }
@@ -336,13 +301,12 @@ async fn bind_telegram_owner(token: &SecretString) -> Result<Option<i64>, Channe
 /// Bind flow when the token already exists (reads from secrets store).
 ///
 /// Retrieves the saved bot token and delegates to `bind_telegram_owner`.
-async fn bind_telegram_owner_flow(
-    secrets: &SecretsContext,
-    settings: &Settings,
-) -> Result<Option<i64>, ChannelSetupError> {
+async fn bind_telegram_owner_flow(secrets: &SecretsContext) -> Result<Option<i64>, String> {
+    // Check current settings first
+    let settings = Settings::load();
     if settings.channels.telegram_owner_id.is_some() {
         print_info("Bot is already bound to a Telegram account.");
-        if !confirm("Re-bind to a different account?", false)? {
+        if !confirm("Re-bind to a different account?", false).map_err(|e| e.to_string())? {
             return Ok(settings.channels.telegram_owner_id);
         }
     }
@@ -357,10 +321,12 @@ async fn bind_telegram_owner_flow(
 ///
 /// This is shared across all channels that need webhook endpoints.
 /// Returns the tunnel URL if configured.
-pub fn setup_tunnel(settings: &Settings) -> Result<Option<String>, ChannelSetupError> {
+pub fn setup_tunnel() -> Result<Option<String>, String> {
+    // Check if already configured
+    let settings = Settings::load();
     if let Some(ref url) = settings.tunnel.public_url {
         print_info(&format!("Existing tunnel configured: {}", url));
-        if !confirm("Change tunnel configuration?", false)? {
+        if !confirm("Change tunnel configuration?", false).map_err(|e| e.to_string())? {
             return Ok(Some(url.clone()));
         }
     }
@@ -380,24 +346,30 @@ pub fn setup_tunnel(settings: &Settings) -> Result<Option<String>, ChannelSetupE
     print_info("Security comes from provider-specific secrets (e.g., Telegram webhook secret).");
     println!();
 
-    if !confirm("Configure a tunnel?", false)? {
+    if !confirm("Configure a tunnel?", false).map_err(|e| e.to_string())? {
         return Ok(None);
     }
 
-    let tunnel_url = input("Tunnel URL (e.g., https://abc123.ngrok.io)")?;
+    let tunnel_url =
+        input("Tunnel URL (e.g., https://abc123.ngrok.io)").map_err(|e| e.to_string())?;
 
     // Validate URL format
     if !tunnel_url.starts_with("https://") {
         print_error("URL must start with https:// (webhooks require HTTPS)");
-        return Err(ChannelSetupError::Validation(
-            "Invalid tunnel URL: must use HTTPS".to_string(),
-        ));
+        return Err("Invalid tunnel URL: must use HTTPS".to_string());
     }
 
     // Remove trailing slash if present
     let tunnel_url = tunnel_url.trim_end_matches('/').to_string();
 
-    print_success(&format!("Tunnel URL configured: {}", tunnel_url));
+    // Save to settings
+    let mut settings = Settings::load();
+    settings.tunnel.public_url = Some(tunnel_url.clone());
+    settings
+        .save()
+        .map_err(|e| format!("Failed to save settings: {}", e))?;
+
+    print_success(&format!("Tunnel URL saved: {}", tunnel_url));
     print_info("");
     print_info("Make sure your tunnel is running before starting the agent.");
     print_info("You can also set TUNNEL_URL environment variable to override.");
@@ -408,11 +380,10 @@ pub fn setup_tunnel(settings: &Settings) -> Result<Option<String>, ChannelSetupE
 /// Set up Telegram webhook secret for signature validation.
 ///
 /// Returns the webhook secret if configured.
-async fn setup_telegram_webhook_secret(
-    secrets: &SecretsContext,
-    tunnel: &TunnelSettings,
-) -> Result<Option<String>, ChannelSetupError> {
-    if tunnel.public_url.is_none() {
+async fn setup_telegram_webhook_secret(secrets: &SecretsContext) -> Result<Option<String>, String> {
+    // Check if tunnel is configured
+    let settings = Settings::load();
+    if settings.tunnel.public_url.is_none() {
         print_info("");
         print_info("No tunnel configured. Telegram will use polling mode (30s+ delay).");
         print_info("Run setup again to configure a tunnel for instant delivery.");
@@ -424,7 +395,7 @@ async fn setup_telegram_webhook_secret(
     print_info("A webhook secret adds an extra layer of security by validating");
     print_info("that requests actually come from Telegram's servers.");
 
-    if !confirm("Generate a webhook secret?", true)? {
+    if !confirm("Generate a webhook secret?", true).map_err(|e| e.to_string())? {
         return Ok(None);
     }
 
@@ -443,13 +414,11 @@ async fn setup_telegram_webhook_secret(
 /// Validate a Telegram bot token by calling the getMe API.
 ///
 /// Returns the bot's username if valid.
-pub async fn validate_telegram_token(
-    token: &SecretString,
-) -> Result<Option<String>, ChannelSetupError> {
+pub async fn validate_telegram_token(token: &SecretString) -> Result<Option<String>, String> {
     let client = Client::builder()
         .timeout(std::time::Duration::from_secs(10))
         .build()
-        .map_err(|e| ChannelSetupError::Network(format!("Failed to create HTTP client: {}", e)))?;
+        .map_err(|e| format!("Failed to create HTTP client: {}", e))?;
 
     let url = format!(
         "https://api.telegram.org/bot{}/getMe",
@@ -460,26 +429,21 @@ pub async fn validate_telegram_token(
         .get(&url)
         .send()
         .await
-        .map_err(|e| ChannelSetupError::Network(format!("Request failed: {}", e)))?;
+        .map_err(|e| format!("Request failed: {}", e))?;
 
     if !response.status().is_success() {
-        return Err(ChannelSetupError::Network(format!(
-            "API returned status {}",
-            response.status()
-        )));
+        return Err(format!("API returned status {}", response.status()));
     }
 
     let body: TelegramGetMeResponse = response
         .json()
         .await
-        .map_err(|e| ChannelSetupError::Network(format!("Failed to parse response: {}", e)))?;
+        .map_err(|e| format!("Failed to parse response: {}", e))?;
 
     if body.ok {
         Ok(body.result.and_then(|u| u.username))
     } else {
-        Err(ChannelSetupError::Network(
-            "Telegram API returned error".to_string(),
-        ))
+        Err("Telegram API returned error".to_string())
     }
 }
 
@@ -492,34 +456,38 @@ pub struct HttpSetupResult {
 }
 
 /// Set up HTTP webhook channel.
-pub async fn setup_http(secrets: &SecretsContext) -> Result<HttpSetupResult, ChannelSetupError> {
+pub async fn setup_http(secrets: &SecretsContext) -> Result<HttpSetupResult, String> {
     println!("HTTP Webhook Setup:");
     println!();
     print_info("The HTTP webhook allows external services to send messages to the agent.");
     println!();
 
-    let port_str = optional_input("Port", Some("default: 8080"))?;
+    let port_str = optional_input("Port", Some("default: 8080")).map_err(|e| e.to_string())?;
     let port: u16 = port_str
         .as_deref()
         .unwrap_or("8080")
         .parse()
-        .map_err(|e| ChannelSetupError::Validation(format!("Invalid port: {}", e)))?;
+        .map_err(|e| format!("Invalid port: {}", e))?;
 
     if port < 1024 {
         print_info("Note: Ports below 1024 may require root privileges");
     }
 
-    let host =
-        optional_input("Host", Some("default: 0.0.0.0"))?.unwrap_or_else(|| "0.0.0.0".to_string());
+    let host = optional_input("Host", Some("default: 0.0.0.0"))
+        .map_err(|e| e.to_string())?
+        .unwrap_or_else(|| "0.0.0.0".to_string());
 
     // Generate a webhook secret
-    if confirm("Generate a webhook secret for authentication?", true)? {
+    if confirm("Generate a webhook secret for authentication?", true).map_err(|e| e.to_string())? {
         let secret = generate_webhook_secret();
         secrets
-            .save_secret("http_webhook_secret", &SecretString::from(secret))
+            .save_secret("http_webhook_secret", &SecretString::from(secret.clone()))
             .await?;
         print_success("Webhook secret generated and saved to database");
-        print_info("Retrieve it later with: ironclaw secret get http_webhook_secret");
+        print_info(&format!(
+            "Secret: {} (store this for your webhook clients)",
+            secret
+        ));
     }
 
     print_success(&format!("HTTP webhook will listen on {}:{}", host, port));
@@ -533,7 +501,11 @@ pub async fn setup_http(secrets: &SecretsContext) -> Result<HttpSetupResult, Cha
 
 /// Generate a random webhook secret.
 pub fn generate_webhook_secret() -> String {
-    generate_secret_with_length(32)
+    use rand::RngCore;
+    let mut rng = rand::thread_rng();
+    let mut bytes = [0u8; 32];
+    rng.fill_bytes(&mut bytes);
+    bytes.iter().map(|b| format!("{:02x}", b)).collect()
 }
 
 /// Result of WASM channel setup.
@@ -551,7 +523,7 @@ pub async fn setup_wasm_channel(
     secrets: &SecretsContext,
     channel_name: &str,
     setup: &crate::channels::wasm::SetupSchema,
-) -> Result<WasmChannelSetupResult, ChannelSetupError> {
+) -> Result<WasmChannelSetupResult, String> {
     println!("{} Setup:", channel_name);
     println!();
 
@@ -562,7 +534,7 @@ pub async fn setup_wasm_channel(
                 "Existing {} found in database.",
                 secret_config.name
             ));
-            if !confirm("Replace existing value?", false)? {
+            if !confirm("Replace existing value?", false).map_err(|e| e.to_string())? {
                 continue;
             }
         }
@@ -570,7 +542,8 @@ pub async fn setup_wasm_channel(
         // Get the value from user or auto-generate
         let value = if secret_config.optional {
             let input_value =
-                optional_input(&secret_config.prompt, Some("leave empty to auto-generate"))?;
+                optional_input(&secret_config.prompt, Some("leave empty to auto-generate"))
+                    .map_err(|e| e.to_string())?;
 
             if let Some(v) = input_value {
                 if !v.is_empty() {
@@ -597,21 +570,18 @@ pub async fn setup_wasm_channel(
             }
         } else {
             // Required secret
-            let input_value = secret_input(&secret_config.prompt)?;
+            let input_value = secret_input(&secret_config.prompt).map_err(|e| e.to_string())?;
 
             // Validate if pattern is provided
             if let Some(ref pattern) = secret_config.validation {
-                let re = regex::Regex::new(pattern).map_err(|e| {
-                    ChannelSetupError::Validation(format!("Invalid validation pattern: {}", e))
-                })?;
+                let re = regex::Regex::new(pattern)
+                    .map_err(|e| format!("Invalid validation pattern: {}", e))?;
                 if !re.is_match(input_value.expose_secret()) {
                     print_error(&format!(
                         "Value does not match expected format: {}",
                         pattern
                     ));
-                    return Err(ChannelSetupError::Validation(
-                        "Validation failed".to_string(),
-                    ));
+                    return Err("Validation failed".to_string());
                 }
             }
 
@@ -623,11 +593,14 @@ pub async fn setup_wasm_channel(
         print_success(&format!("{} saved to database", secret_config.name));
     }
 
-    // TODO: Substitute secrets into the validation URL and make a
-    // GET request to verify the configured credentials actually work.
+    // Optionally validate the configuration
     if let Some(ref validation_endpoint) = setup.validation_endpoint {
+        print_info("Validating configuration...");
+        // The validation endpoint may contain placeholders like {telegram_bot_token}
+        // For now, we skip validation since we'd need to substitute secrets
+        // A full implementation would fetch secrets and substitute them
         print_info(&format!(
-            "Validation endpoint configured: {} (validation not yet implemented)",
+            "Validation endpoint configured: {} (validation skipped)",
             validation_endpoint
         ));
     }
@@ -651,23 +624,11 @@ fn generate_secret_with_length(length: usize) -> String {
 
 #[cfg(test)]
 mod tests {
-    use crate::setup::channels::generate_webhook_secret;
+    use super::*;
 
     #[test]
     fn test_generate_webhook_secret() {
         let secret = generate_webhook_secret();
         assert_eq!(secret.len(), 64); // 32 bytes = 64 hex chars
     }
-
-    #[test]
-    fn test_generate_secret_with_length() {
-        use super::generate_secret_with_length;
-
-        let s = generate_secret_with_length(16);
-        assert_eq!(s.len(), 32); // 16 bytes = 32 hex chars
-        assert!(s.chars().all(|c| c.is_ascii_hexdigit()));
-
-        let s2 = generate_secret_with_length(1);
-        assert_eq!(s2.len(), 2);
-    }
 }

src/setup/mod.rs

@@ -3,7 +3,7 @@
 //! Provides a guided setup experience for:
 //! 1. Database connection
 //! 2. Security (secrets master key)
-//! 3. Inference provider selection
+//! 3. NEAR AI authentication
 //! 4. Model selection
 //! 5. Embeddings
 //! 6. Channel configuration (HTTP, Telegram, etc.)
@@ -24,8 +24,7 @@ mod prompts;
 mod wizard;
 
 pub use channels::{
-    ChannelSetupError, SecretsContext, setup_http, setup_telegram, setup_tunnel,
-    validate_telegram_token,
+    SecretsContext, setup_http, setup_telegram, setup_tunnel, validate_telegram_token,
 };
 pub use prompts::{
     confirm, input, optional_input, print_error, print_header, print_info, print_step,

src/setup/prompts.rs

@@ -21,7 +21,6 @@ use secrecy::SecretString;
 /// Display a numbered menu and get user selection.
 ///
 /// Returns the index (0-based) of the selected option.
-/// Pressing Enter without input selects the first option (index 0).
 ///
 /// # Example
 ///
@@ -55,11 +54,10 @@ pub fn select_one(prompt: &str, options: &[&str]) -> io::Result<usize> {
         }
 
         // Parse number
-        if let Ok(num) = input.parse::<usize>()
-            && num >= 1
-            && num <= options.len()
-        {
-            return Ok(num - 1);
+        if let Ok(num) = input.parse::<usize>() {
+            if num >= 1 && num <= options.len() {
+                return Ok(num - 1);
+            }
         }
 
         writeln!(
@@ -85,10 +83,6 @@ pub fn select_one(prompt: &str, options: &[&str]) -> io::Result<usize> {
 /// ])?;
 /// ```
 pub fn select_many(prompt: &str, options: &[(&str, bool)]) -> io::Result<Vec<usize>> {
-    if options.is_empty() {
-        return Ok(vec![]);
-    }
-
     let mut stdout = io::stdout();
     let mut selected: Vec<bool> = options.iter().map(|(_, s)| *s).collect();
     let mut cursor_pos = 0;

src/tools/builder/testing.rs

@@ -326,20 +326,20 @@ impl TestHarness {
                 }
 
                 // Verify expected output
-                if let Some(ref expected) = test.expected_output
-                    && &actual != expected
-                {
-                    return TestResult {
-                        name: test.name.clone(),
-                        passed: false,
-                        duration,
-                        error: Some(format!(
-                            "Output mismatch:\nExpected: {}\nActual: {}",
-                            serde_json::to_string_pretty(expected).unwrap_or_default(),
-                            serde_json::to_string_pretty(&actual).unwrap_or_default()
-                        )),
-                        actual_output: Some(actual),
-                    };
+                if let Some(ref expected) = test.expected_output {
+                    if &actual != expected {
+                        return TestResult {
+                            name: test.name.clone(),
+                            passed: false,
+                            duration,
+                            error: Some(format!(
+                                "Output mismatch:\nExpected: {}\nActual: {}",
+                                serde_json::to_string_pretty(expected).unwrap_or_default(),
+                                serde_json::to_string_pretty(&actual).unwrap_or_default()
+                            )),
+                            actual_output: Some(actual),
+                        };
+                    }
                 }
 
                 // Verify expected fields
@@ -357,19 +357,19 @@ impl TestHarness {
                             };
                         }
 
-                        if let Some(ref expected_value) = field.value
-                            && field_value != Some(expected_value)
-                        {
-                            return TestResult {
-                                name: test.name.clone(),
-                                passed: false,
-                                duration,
-                                error: Some(format!(
-                                    "Field '{}' mismatch: expected {:?}, got {:?}",
-                                    field.path, expected_value, field_value
-                                )),
-                                actual_output: Some(actual),
-                            };
+                        if let Some(ref expected_value) = field.value {
+                            if field_value != Some(expected_value) {
+                                return TestResult {
+                                    name: test.name.clone(),
+                                    passed: false,
+                                    duration,
+                                    error: Some(format!(
+                                        "Field '{}' mismatch: expected {:?}, got {:?}",
+                                        field.path, expected_value, field_value
+                                    )),
+                                    actual_output: Some(actual),
+                                };
+                            }
                         }
                     }
                 }

src/tools/builtin/echo.rs

@@ -3,7 +3,7 @@
 use async_trait::async_trait;
 
 use crate::context::JobContext;
-use crate::tools::tool::{Tool, ToolError, ToolOutput, require_str};
+use crate::tools::tool::{Tool, ToolError, ToolOutput};
 
 /// Simple echo tool for testing.
 pub struct EchoTool;
@@ -38,7 +38,12 @@ impl Tool for EchoTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let message = require_str(&params, "message")?;
+        let message = params
+            .get("message")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| {
+                ToolError::InvalidParameters("missing 'message' parameter".to_string())
+            })?;
 
         Ok(ToolOutput::text(message, start.elapsed()))
     }

src/tools/builtin/ecommerce.rs

@@ -0,0 +1,136 @@
+//! E-commerce tool for shopping and price comparison.
+
+use async_trait::async_trait;
+
+use crate::context::JobContext;
+use crate::tools::tool::{Tool, ToolError, ToolOutput};
+
+/// Tool for e-commerce operations (Amazon, price comparison, etc.).
+pub struct EcommerceTool {
+    // TODO: Add API clients
+}
+
+impl EcommerceTool {
+    /// Create a new e-commerce tool.
+    pub fn new() -> Self {
+        Self {}
+    }
+}
+
+impl Default for EcommerceTool {
+    fn default() -> Self {
+        Self::new()
+    }
+}
+
+#[async_trait]
+impl Tool for EcommerceTool {
+    fn name(&self) -> &str {
+        "ecommerce"
+    }
+
+    fn description(&self) -> &str {
+        "Search products, compare prices, and find deals across e-commerce platforms."
+    }
+
+    fn parameters_schema(&self) -> serde_json::Value {
+        serde_json::json!({
+            "type": "object",
+            "properties": {
+                "action": {
+                    "type": "string",
+                    "enum": ["search", "get_product", "compare_prices", "track_price"],
+                    "description": "The e-commerce action to perform"
+                },
+                "query": {
+                    "type": "string",
+                    "description": "Search query (for search action)"
+                },
+                "product_id": {
+                    "type": "string",
+                    "description": "Product ID or ASIN (for get_product, compare_prices)"
+                },
+                "platform": {
+                    "type": "string",
+                    "enum": ["amazon", "ebay", "walmart", "all"],
+                    "description": "E-commerce platform to search"
+                },
+                "max_price": {
+                    "type": "number",
+                    "description": "Maximum price filter"
+                },
+                "category": {
+                    "type": "string",
+                    "description": "Product category filter"
+                }
+            },
+            "required": ["action"]
+        })
+    }
+
+    async fn execute(
+        &self,
+        params: serde_json::Value,
+        _ctx: &JobContext,
+    ) -> Result<ToolOutput, ToolError> {
+        let start = std::time::Instant::now();
+
+        let action = params
+            .get("action")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| {
+                ToolError::InvalidParameters("missing 'action' parameter".to_string())
+            })?;
+
+        // TODO: Implement actual e-commerce API integrations
+        let result = match action {
+            "search" => {
+                let query = params.get("query").and_then(|v| v.as_str()).unwrap_or("");
+
+                serde_json::json!({
+                    "query": query,
+                    "results": [],
+                    "message": "E-commerce integration not yet implemented"
+                })
+            }
+            "get_product" => {
+                let product_id = params
+                    .get("product_id")
+                    .and_then(|v| v.as_str())
+                    .ok_or_else(|| {
+                        ToolError::InvalidParameters("missing 'product_id' parameter".to_string())
+                    })?;
+
+                serde_json::json!({
+                    "product_id": product_id,
+                    "found": false,
+                    "message": "E-commerce integration not yet implemented"
+                })
+            }
+            "compare_prices" => {
+                serde_json::json!({
+                    "prices": [],
+                    "message": "E-commerce integration not yet implemented"
+                })
+            }
+            "track_price" => {
+                serde_json::json!({
+                    "tracking": false,
+                    "message": "E-commerce integration not yet implemented"
+                })
+            }
+            _ => {
+                return Err(ToolError::InvalidParameters(format!(
+                    "unknown action: {}",
+                    action
+                )));
+            }
+        };
+
+        Ok(ToolOutput::success(result, start.elapsed()))
+    }
+
+    fn requires_sanitization(&self) -> bool {
+        true // External e-commerce data
+    }
+}

src/tools/builtin/extension_tools.rs

@@ -9,7 +9,7 @@ use async_trait::async_trait;
 
 use crate::context::JobContext;
 use crate::extensions::{ExtensionKind, ExtensionManager};
-use crate::tools::tool::{Tool, ToolError, ToolOutput, require_str};
+use crate::tools::tool::{Tool, ToolError, ToolOutput};
 
 // ── tool_search ──────────────────────────────────────────────────────────
 
@@ -133,7 +133,10 @@ impl Tool for ToolInstallTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let name = require_str(&params, "name")?;
+        let name = params
+            .get("name")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("name is required".to_string()))?;
 
         let url = params.get("url").and_then(|v| v.as_str());
 
@@ -207,7 +210,10 @@ impl Tool for ToolAuthTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let name = require_str(&params, "name")?;
+        let name = params
+            .get("name")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("name is required".to_string()))?;
 
         let result = self
             .manager
@@ -300,7 +306,10 @@ impl Tool for ToolActivateTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let name = require_str(&params, "name")?;
+        let name = params
+            .get("name")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("name is required".to_string()))?;
 
         match self.manager.activate(name).await {
             Ok(result) => {
@@ -462,7 +471,10 @@ impl Tool for ToolRemoveTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let name = require_str(&params, "name")?;
+        let name = params
+            .get("name")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("name is required".to_string()))?;
 
         let message = self
             .manager

src/tools/builtin/file.rs

@@ -11,7 +11,7 @@ use async_trait::async_trait;
 use tokio::fs;
 
 use crate::context::JobContext;
-use crate::tools::tool::{Tool, ToolDomain, ToolError, ToolOutput, require_str};
+use crate::tools::tool::{Tool, ToolDomain, ToolError, ToolOutput};
 use crate::workspace::paths as ws_paths;
 
 /// Well-known workspace filenames that must go through memory_write, not write_file.
@@ -203,7 +203,10 @@ impl Tool for ReadFileTool {
         params: serde_json::Value,
         _ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
-        let path_str = require_str(&params, "path")?;
+        let path_str = params
+            .get("path")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'path' parameter".into()))?;
 
         let offset = params.get("offset").and_then(|v| v.as_u64()).unwrap_or(0) as usize;
         let limit = params.get("limit").and_then(|v| v.as_u64());
@@ -325,7 +328,10 @@ impl Tool for WriteFileTool {
         params: serde_json::Value,
         _ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
-        let path_str = require_str(&params, "path")?;
+        let path_str = params
+            .get("path")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'path' parameter".into()))?;
 
         // Reject workspace paths: these live in the database, not on disk.
         if is_workspace_path(path_str) {
@@ -336,7 +342,10 @@ impl Tool for WriteFileTool {
             )));
         }
 
-        let content = require_str(&params, "content")?;
+        let content = params
+            .get("content")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'content' parameter".into()))?;
 
         let start = std::time::Instant::now();
 
@@ -641,11 +650,20 @@ impl Tool for ApplyPatchTool {
         params: serde_json::Value,
         _ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
-        let path_str = require_str(&params, "path")?;
+        let path_str = params
+            .get("path")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'path' parameter".into()))?;
 
-        let old_string = require_str(&params, "old_string")?;
+        let old_string = params
+            .get("old_string")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'old_string' parameter".into()))?;
 
-        let new_string = require_str(&params, "new_string")?;
+        let new_string = params
+            .get("new_string")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'new_string' parameter".into()))?;
 
         let replace_all = params
             .get("replace_all")

src/tools/builtin/http.rs

@@ -5,18 +5,13 @@ use std::net::{IpAddr, ToSocketAddrs};
 use std::time::Duration;
 
 use async_trait::async_trait;
-use futures::StreamExt;
 use reqwest::Client;
 
 use crate::context::JobContext;
 use crate::safety::LeakDetector;
-use crate::tools::tool::{Tool, ToolError, ToolOutput, require_str};
+use crate::tools::tool::{Tool, ToolError, ToolOutput};
 
-/// Maximum response body size (5 MB).
-///
-/// 5 MB is large enough for typical JSON API responses and moderate HTML pages,
-/// but small enough to prevent OOM from malicious or runaway servers.  The WASM
-/// HTTP wrapper uses the same limit for consistency.
+/// Maximum response body size (5 MB). Prevents OOM from unbounded responses.
 const MAX_RESPONSE_SIZE: usize = 5 * 1024 * 1024;
 
 /// Tool for making HTTP requests.
@@ -59,12 +54,12 @@ fn validate_url(url: &str) -> Result<reqwest::Url, ToolError> {
     }
 
     // Check literal IP addresses
-    if let Ok(ip) = host.parse::<IpAddr>()
-        && is_disallowed_ip(&ip)
-    {
-        return Err(ToolError::NotAuthorized(
-            "private or local IPs are not allowed".to_string(),
-        ));
+    if let Ok(ip) = host.parse::<IpAddr>() {
+        if is_disallowed_ip(&ip) {
+            return Err(ToolError::NotAuthorized(
+                "private or local IPs are not allowed".to_string(),
+            ));
+        }
     }
 
     // Resolve hostname and check all resolved IPs against the blocklist.
@@ -159,9 +154,17 @@ impl Tool for HttpTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let method = require_str(&params, "method")?;
+        let method = params
+            .get("method")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| {
+                ToolError::InvalidParameters("missing 'method' parameter".to_string())
+            })?;
 
-        let url = require_str(&params, "url")?;
+        let url = params
+            .get("url")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'url' parameter".to_string()))?;
         let parsed_url = validate_url(url)?;
 
         // Parse headers
@@ -235,43 +238,19 @@ impl Tool for HttpTool {
             .filter_map(|(k, v)| v.to_str().ok().map(|v| (k.to_string(), v.to_string())))
             .collect();
 
-        // Pre-check Content-Length header to reject obviously oversized responses
-        // before downloading anything, preventing OOM from malicious servers.
-        if let Some(content_length) = response.headers().get(reqwest::header::CONTENT_LENGTH)
-            && let Ok(s) = content_length.to_str()
-            && let Ok(len) = s.parse::<usize>()
-            && len > MAX_RESPONSE_SIZE
-        {
-            tracing::warn!(
-                url = %parsed_url,
-                content_length = len,
-                max = MAX_RESPONSE_SIZE,
-                "Rejected HTTP response: Content-Length exceeds limit"
-            );
+        // Get response body with size cap to prevent OOM
+        let body_bytes = response.bytes().await.map_err(|e| {
+            ToolError::ExternalService(format!("failed to read response body: {}", e))
+        })?;
+
+        if body_bytes.len() > MAX_RESPONSE_SIZE {
             return Err(ToolError::ExecutionFailed(format!(
-                "Response Content-Length ({} bytes) exceeds maximum allowed size ({} bytes)",
-                len, MAX_RESPONSE_SIZE
+                "Response body too large ({} bytes, max {})",
+                body_bytes.len(),
+                MAX_RESPONSE_SIZE
             )));
         }
 
-        // Stream the response body with a hard size cap. Even if Content-Length was
-        // absent or lied about the size, we stop reading once we exceed the limit.
-        let mut body = Vec::new();
-        let mut stream = response.bytes_stream();
-        while let Some(chunk) = StreamExt::next(&mut stream).await {
-            let chunk = chunk.map_err(|e| {
-                ToolError::ExternalService(format!("failed to read response body: {}", e))
-            })?;
-            if body.len() + chunk.len() > MAX_RESPONSE_SIZE {
-                return Err(ToolError::ExecutionFailed(format!(
-                    "Response body exceeds maximum allowed size ({} bytes)",
-                    MAX_RESPONSE_SIZE
-                )));
-            }
-            body.extend_from_slice(&chunk);
-        }
-        let body_bytes = bytes::Bytes::from(body);
-
         let body_text = String::from_utf8_lossy(&body_bytes).into_owned();
 
         // Try to parse as JSON, fall back to string
@@ -357,10 +336,4 @@ mod tests {
         // Public
         assert!(!is_disallowed_ip(&IpAddr::V4(Ipv4Addr::new(8, 8, 8, 8))));
     }
-
-    #[test]
-    fn test_max_response_size_is_reasonable() {
-        // MAX_RESPONSE_SIZE should be 5 MB to prevent OOM while allowing typical API responses.
-        assert_eq!(MAX_RESPONSE_SIZE, 5 * 1024 * 1024);
-    }
 }

src/tools/builtin/job.rs

@@ -18,7 +18,7 @@ use crate::context::{ContextManager, JobContext, JobState};
 use crate::db::Database;
 use crate::history::SandboxJobRecord;
 use crate::orchestrator::job_manager::{ContainerJobManager, JobMode};
-use crate::tools::tool::{Tool, ToolError, ToolOutput, require_str};
+use crate::tools::tool::{Tool, ToolError, ToolOutput};
 
 /// Tool for creating a new job.
 ///
@@ -158,18 +158,18 @@ impl CreateJobTool {
         });
 
         // Persist the job mode to DB
-        if mode == JobMode::ClaudeCode
-            && let Some(store) = self.store.clone()
-        {
-            let job_id_copy = job_id;
-            tokio::spawn(async move {
-                if let Err(e) = store
-                    .update_sandbox_job_mode(job_id_copy, "claude_code")
-                    .await
-                {
-                    tracing::warn!(job_id = %job_id_copy, "Failed to set job mode: {}", e);
-                }
-            });
+        if mode == JobMode::ClaudeCode {
+            if let Some(store) = self.store.clone() {
+                let job_id_copy = job_id;
+                tokio::spawn(async move {
+                    if let Err(e) = store
+                        .update_sandbox_job_mode(job_id_copy, "claude_code")
+                        .await
+                    {
+                        tracing::warn!(job_id = %job_id_copy, "Failed to set job mode: {}", e);
+                    }
+                });
+            }
         }
 
         // Create the container job with the pre-determined job_id.
@@ -467,9 +467,17 @@ impl Tool for CreateJobTool {
         params: serde_json::Value,
         ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
-        let title = require_str(&params, "title")?;
+        let title = params
+            .get("title")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'title' parameter".into()))?;
 
-        let description = require_str(&params, "description")?;
+        let description = params
+            .get("description")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| {
+                ToolError::InvalidParameters("missing 'description' parameter".into())
+            })?;
 
         if self.sandbox_enabled() {
             let wait = params.get("wait").and_then(|v| v.as_bool()).unwrap_or(true);
@@ -627,7 +635,10 @@ impl Tool for JobStatusTool {
         let start = std::time::Instant::now();
         let requester_id = ctx.user_id.clone();
 
-        let job_id_str = require_str(&params, "job_id")?;
+        let job_id_str = params
+            .get("job_id")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'job_id' parameter".into()))?;
 
         let job_id = Uuid::parse_str(job_id_str).map_err(|_| {
             ToolError::InvalidParameters(format!("invalid job ID format: {}", job_id_str))
@@ -709,7 +720,10 @@ impl Tool for CancelJobTool {
         let start = std::time::Instant::now();
         let requester_id = ctx.user_id.clone();
 
-        let job_id_str = require_str(&params, "job_id")?;
+        let job_id_str = params
+            .get("job_id")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'job_id' parameter".into()))?;
 
         let job_id = Uuid::parse_str(job_id_str).map_err(|_| {
             ToolError::InvalidParameters(format!("invalid job ID format: {}", job_id_str))

src/tools/builtin/json.rs

@@ -3,7 +3,7 @@
 use async_trait::async_trait;
 
 use crate::context::JobContext;
-use crate::tools::tool::{Tool, ToolError, ToolOutput, require_param, require_str};
+use crate::tools::tool::{Tool, ToolError, ToolOutput};
 
 /// Tool for JSON manipulation (parse, query, transform).
 pub struct JsonTool;
@@ -46,9 +46,16 @@ impl Tool for JsonTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let operation = require_str(&params, "operation")?;
+        let operation = params
+            .get("operation")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| {
+                ToolError::InvalidParameters("missing 'operation' parameter".to_string())
+            })?;
 
-        let data = require_param(&params, "data")?;
+        let data = params
+            .get("data")
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'data' parameter".to_string()))?;
 
         let result = match operation {
             "parse" => {

src/tools/builtin/marketplace.rs

@@ -0,0 +1,160 @@
+//! NEAR AI Marketplace tool.
+
+use async_trait::async_trait;
+use rust_decimal::Decimal;
+
+use crate::context::JobContext;
+use crate::tools::tool::{Tool, ToolError, ToolOutput};
+
+/// Tool for interacting with the NEAR AI marketplace.
+pub struct MarketplaceTool {
+    // TODO: Add marketplace client
+}
+
+impl MarketplaceTool {
+    /// Create a new marketplace tool.
+    pub fn new() -> Self {
+        Self {}
+    }
+}
+
+impl Default for MarketplaceTool {
+    fn default() -> Self {
+        Self::new()
+    }
+}
+
+#[async_trait]
+impl Tool for MarketplaceTool {
+    fn name(&self) -> &str {
+        "marketplace"
+    }
+
+    fn description(&self) -> &str {
+        "Interact with the NEAR AI marketplace: search jobs, submit bids, deliver work."
+    }
+
+    fn parameters_schema(&self) -> serde_json::Value {
+        serde_json::json!({
+            "type": "object",
+            "properties": {
+                "action": {
+                    "type": "string",
+                    "enum": ["search_jobs", "get_job", "submit_bid", "accept_job", "submit_work", "get_status"],
+                    "description": "The marketplace action to perform"
+                },
+                "job_id": {
+                    "type": "string",
+                    "description": "Job ID (for get_job, submit_bid, accept_job, submit_work)"
+                },
+                "query": {
+                    "type": "string",
+                    "description": "Search query (for search_jobs)"
+                },
+                "category": {
+                    "type": "string",
+                    "description": "Job category filter (for search_jobs)"
+                },
+                "bid_amount": {
+                    "type": "number",
+                    "description": "Bid amount in NEAR (for submit_bid)"
+                },
+                "work_url": {
+                    "type": "string",
+                    "description": "URL to submitted work (for submit_work)"
+                },
+                "work_description": {
+                    "type": "string",
+                    "description": "Description of completed work (for submit_work)"
+                }
+            },
+            "required": ["action"]
+        })
+    }
+
+    async fn execute(
+        &self,
+        params: serde_json::Value,
+        _ctx: &JobContext,
+    ) -> Result<ToolOutput, ToolError> {
+        let start = std::time::Instant::now();
+
+        let action = params
+            .get("action")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| {
+                ToolError::InvalidParameters("missing 'action' parameter".to_string())
+            })?;
+
+        // TODO: Implement actual marketplace integration
+        let result = match action {
+            "search_jobs" => {
+                // Placeholder response
+                serde_json::json!({
+                    "jobs": [],
+                    "total": 0,
+                    "message": "Marketplace integration not yet implemented"
+                })
+            }
+            "get_job" => {
+                let job_id = params
+                    .get("job_id")
+                    .and_then(|v| v.as_str())
+                    .ok_or_else(|| {
+                        ToolError::InvalidParameters("missing 'job_id' parameter".to_string())
+                    })?;
+
+                serde_json::json!({
+                    "job_id": job_id,
+                    "status": "not_found",
+                    "message": "Marketplace integration not yet implemented"
+                })
+            }
+            "submit_bid" => {
+                serde_json::json!({
+                    "success": false,
+                    "message": "Marketplace integration not yet implemented"
+                })
+            }
+            "accept_job" => {
+                serde_json::json!({
+                    "success": false,
+                    "message": "Marketplace integration not yet implemented"
+                })
+            }
+            "submit_work" => {
+                serde_json::json!({
+                    "success": false,
+                    "message": "Marketplace integration not yet implemented"
+                })
+            }
+            "get_status" => {
+                serde_json::json!({
+                    "connected": false,
+                    "message": "Marketplace integration not yet implemented"
+                })
+            }
+            _ => {
+                return Err(ToolError::InvalidParameters(format!(
+                    "unknown action: {}",
+                    action
+                )));
+            }
+        };
+
+        Ok(ToolOutput::success(result, start.elapsed()))
+    }
+
+    fn estimated_cost(&self, params: &serde_json::Value) -> Option<Decimal> {
+        // Bidding has a cost
+        if params.get("action").and_then(|v| v.as_str()) == Some("submit_bid") {
+            Some(Decimal::new(1, 2)) // 0.01 NEAR gas cost
+        } else {
+            None
+        }
+    }
+
+    fn requires_sanitization(&self) -> bool {
+        true // External marketplace data
+    }
+}

src/tools/builtin/memory.rs

@@ -17,7 +17,7 @@ use std::sync::Arc;
 use async_trait::async_trait;
 
 use crate::context::JobContext;
-use crate::tools::tool::{Tool, ToolError, ToolOutput, require_str};
+use crate::tools::tool::{Tool, ToolError, ToolOutput};
 use crate::workspace::{Workspace, paths};
 
 /// Identity files that the LLM must not overwrite via tool calls.
@@ -81,7 +81,10 @@ impl Tool for MemorySearchTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let query = require_str(&params, "query")?;
+        let query = params
+            .get("query")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'query' parameter".to_string()))?;
 
         let limit = params
             .get("limit")
@@ -173,7 +176,12 @@ impl Tool for MemoryWriteTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let content = require_str(&params, "content")?;
+        let content = params
+            .get("content")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| {
+                ToolError::InvalidParameters("missing 'content' parameter".to_string())
+            })?;
 
         if content.trim().is_empty() {
             return Err(ToolError::InvalidParameters(
@@ -329,7 +337,10 @@ impl Tool for MemoryReadTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let path = require_str(&params, "path")?;
+        let path = params
+            .get("path")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'path' parameter".to_string()))?;
 
         let doc = self
             .workspace

src/tools/builtin/mod.rs

@@ -1,17 +1,22 @@
 //! Built-in tools that come with the agent.
 
 mod echo;
+mod ecommerce;
 pub mod extension_tools;
 mod file;
 mod http;
 mod job;
 mod json;
+mod marketplace;
 mod memory;
+mod restaurant;
 pub mod routine;
 pub(crate) mod shell;
+mod taskrabbit;
 mod time;
 
 pub use echo::EchoTool;
+pub use ecommerce::EcommerceTool;
 pub use extension_tools::{
     ToolActivateTool, ToolAuthTool, ToolInstallTool, ToolListTool, ToolRemoveTool, ToolSearchTool,
 };
@@ -19,9 +24,12 @@ pub use file::{ApplyPatchTool, ListDirTool, ReadFileTool, WriteFileTool};
 pub use http::HttpTool;
 pub use job::{CancelJobTool, CreateJobTool, JobStatusTool, ListJobsTool};
 pub use json::JsonTool;
+pub use marketplace::MarketplaceTool;
 pub use memory::{MemoryReadTool, MemorySearchTool, MemoryTreeTool, MemoryWriteTool};
+pub use restaurant::RestaurantTool;
 pub use routine::{
     RoutineCreateTool, RoutineDeleteTool, RoutineHistoryTool, RoutineListTool, RoutineUpdateTool,
 };
 pub use shell::ShellTool;
+pub use taskrabbit::TaskRabbitTool;
 pub use time::TimeTool;

src/tools/builtin/restaurant.rs

@@ -0,0 +1,172 @@
+//! Restaurant reservation tool.
+
+use async_trait::async_trait;
+
+use crate::context::JobContext;
+use crate::tools::tool::{Tool, ToolError, ToolOutput};
+
+/// Tool for restaurant reservations (OpenTable, Resy, etc.).
+pub struct RestaurantTool {
+    // TODO: Add reservation API clients
+}
+
+impl RestaurantTool {
+    /// Create a new restaurant tool.
+    pub fn new() -> Self {
+        Self {}
+    }
+}
+
+impl Default for RestaurantTool {
+    fn default() -> Self {
+        Self::new()
+    }
+}
+
+#[async_trait]
+impl Tool for RestaurantTool {
+    fn name(&self) -> &str {
+        "restaurant"
+    }
+
+    fn description(&self) -> &str {
+        "Search restaurants, check availability, and make reservations via OpenTable, Resy, etc."
+    }
+
+    fn parameters_schema(&self) -> serde_json::Value {
+        serde_json::json!({
+            "type": "object",
+            "properties": {
+                "action": {
+                    "type": "string",
+                    "enum": ["search", "check_availability", "make_reservation", "cancel_reservation", "get_reservation"],
+                    "description": "The restaurant action to perform"
+                },
+                "query": {
+                    "type": "string",
+                    "description": "Search query (cuisine type, restaurant name, etc.)"
+                },
+                "location": {
+                    "type": "object",
+                    "properties": {
+                        "city": { "type": "string" },
+                        "neighborhood": { "type": "string" },
+                        "latitude": { "type": "number" },
+                        "longitude": { "type": "number" }
+                    },
+                    "description": "Location to search near"
+                },
+                "date": {
+                    "type": "string",
+                    "description": "Reservation date (YYYY-MM-DD)"
+                },
+                "time": {
+                    "type": "string",
+                    "description": "Preferred time (HH:MM)"
+                },
+                "party_size": {
+                    "type": "integer",
+                    "description": "Number of guests"
+                },
+                "restaurant_id": {
+                    "type": "string",
+                    "description": "Restaurant ID (for check_availability, make_reservation)"
+                },
+                "reservation_id": {
+                    "type": "string",
+                    "description": "Reservation ID (for cancel_reservation, get_reservation)"
+                },
+                "guest_name": {
+                    "type": "string",
+                    "description": "Name for the reservation"
+                },
+                "guest_phone": {
+                    "type": "string",
+                    "description": "Phone number for the reservation"
+                },
+                "guest_email": {
+                    "type": "string",
+                    "description": "Email for the reservation"
+                }
+            },
+            "required": ["action"]
+        })
+    }
+
+    async fn execute(
+        &self,
+        params: serde_json::Value,
+        _ctx: &JobContext,
+    ) -> Result<ToolOutput, ToolError> {
+        let start = std::time::Instant::now();
+
+        let action = params
+            .get("action")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| {
+                ToolError::InvalidParameters("missing 'action' parameter".to_string())
+            })?;
+
+        // TODO: Implement actual restaurant reservation API integrations
+        let result = match action {
+            "search" => {
+                let query = params.get("query").and_then(|v| v.as_str()).unwrap_or("");
+
+                serde_json::json!({
+                    "query": query,
+                    "restaurants": [],
+                    "message": "Restaurant integration not yet implemented"
+                })
+            }
+            "check_availability" => {
+                let restaurant_id = params
+                    .get("restaurant_id")
+                    .and_then(|v| v.as_str())
+                    .ok_or_else(|| {
+                        ToolError::InvalidParameters(
+                            "missing 'restaurant_id' parameter".to_string(),
+                        )
+                    })?;
+
+                serde_json::json!({
+                    "restaurant_id": restaurant_id,
+                    "available_times": [],
+                    "message": "Restaurant integration not yet implemented"
+                })
+            }
+            "make_reservation" => {
+                serde_json::json!({
+                    "success": false,
+                    "message": "Restaurant integration not yet implemented"
+                })
+            }
+            "cancel_reservation" => {
+                serde_json::json!({
+                    "cancelled": false,
+                    "message": "Restaurant integration not yet implemented"
+                })
+            }
+            "get_reservation" => {
+                let reservation_id = params.get("reservation_id").and_then(|v| v.as_str());
+
+                serde_json::json!({
+                    "reservation_id": reservation_id,
+                    "found": false,
+                    "message": "Restaurant integration not yet implemented"
+                })
+            }
+            _ => {
+                return Err(ToolError::InvalidParameters(format!(
+                    "unknown action: {}",
+                    action
+                )));
+            }
+        };
+
+        Ok(ToolOutput::success(result, start.elapsed()))
+    }
+
+    fn requires_sanitization(&self) -> bool {
+        true // External restaurant data
+    }
+}

src/tools/builtin/routine.rs

@@ -20,7 +20,7 @@ use crate::agent::routine::{
 use crate::agent::routine_engine::RoutineEngine;
 use crate::context::JobContext;
 use crate::db::Database;
-use crate::tools::tool::{Tool, ToolError, ToolOutput, require_str};
+use crate::tools::tool::{Tool, ToolError, ToolOutput};
 
 // ==================== routine_create ====================
 
@@ -106,16 +106,25 @@ impl Tool for RoutineCreateTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let name = require_str(&params, "name")?;
+        let name = params
+            .get("name")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'name'".to_string()))?;
 
         let description = params
             .get("description")
             .and_then(|v| v.as_str())
             .unwrap_or("");
 
-        let trigger_type = require_str(&params, "trigger_type")?;
+        let trigger_type = params
+            .get("trigger_type")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'trigger_type'".to_string()))?;
 
-        let prompt = require_str(&params, "prompt")?;
+        let prompt = params
+            .get("prompt")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'prompt'".to_string()))?;
 
         // Build trigger
         let trigger = match trigger_type {
@@ -399,7 +408,10 @@ impl Tool for RoutineUpdateTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let name = require_str(&params, "name")?;
+        let name = params
+            .get("name")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'name'".to_string()))?;
 
         let mut routine = self
             .store
@@ -502,7 +514,10 @@ impl Tool for RoutineDeleteTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let name = require_str(&params, "name")?;
+        let name = params
+            .get("name")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'name'".to_string()))?;
 
         let routine = self
             .store
@@ -580,7 +595,10 @@ impl Tool for RoutineHistoryTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let name = require_str(&params, "name")?;
+        let name = params
+            .get("name")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'name'".to_string()))?;
 
         let limit = params
             .get("limit")

src/tools/builtin/shell.rs

@@ -30,7 +30,7 @@ use tokio::process::Command;
 
 use crate::context::JobContext;
 use crate::sandbox::{SandboxManager, SandboxPolicy};
-use crate::tools::tool::{Tool, ToolDomain, ToolError, ToolOutput, require_str};
+use crate::tools::tool::{Tool, ToolDomain, ToolError, ToolOutput};
 
 /// Maximum output size before truncation (64KB).
 const MAX_OUTPUT_SIZE: usize = 64 * 1024;
@@ -343,12 +343,12 @@ impl ShellTool {
 
         // Use sandbox if configured; fail-closed (never silently fall through
         // to unsandboxed execution when sandbox was intended).
-        if let Some(ref sandbox) = self.sandbox
-            && (sandbox.is_initialized() || sandbox.config().enabled)
-        {
-            return self
-                .execute_sandboxed(sandbox, cmd, &cwd, timeout_duration)
-                .await;
+        if let Some(ref sandbox) = self.sandbox {
+            if sandbox.is_initialized() || sandbox.config().enabled {
+                return self
+                    .execute_sandboxed(sandbox, cmd, &cwd, timeout_duration)
+                    .await;
+            }
         }
 
         // Only execute directly when no sandbox was configured at all.
@@ -401,7 +401,10 @@ impl Tool for ShellTool {
         params: serde_json::Value,
         _ctx: &JobContext,
     ) -> Result<ToolOutput, ToolError> {
-        let command = require_str(&params, "command")?;
+        let command = params
+            .get("command")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| ToolError::InvalidParameters("missing 'command' parameter".into()))?;
 
         let workdir = params.get("workdir").and_then(|v| v.as_str());
         let timeout = params.get("timeout").and_then(|v| v.as_u64());
@@ -426,26 +429,6 @@ impl Tool for ShellTool {
         true // Shell commands should require approval
     }
 
-    fn requires_approval_for(&self, params: &serde_json::Value) -> bool {
-        let cmd = params
-            .get("command")
-            .and_then(|c| c.as_str().map(String::from))
-            .or_else(|| {
-                params
-                    .as_str()
-                    .and_then(|s| serde_json::from_str::<serde_json::Value>(s).ok())
-                    .and_then(|v| v.get("command").and_then(|c| c.as_str().map(String::from)))
-            });
-
-        if let Some(ref cmd) = cmd
-            && requires_explicit_approval(cmd)
-        {
-            return true;
-        }
-
-        false
-    }
-
     fn requires_sanitization(&self) -> bool {
         true // Shell output could contain anything
     }
@@ -544,76 +527,6 @@ mod tests {
         ));
     }
 
-    /// Replicate the extraction logic from agent_loop.rs to prove it works
-    /// when `arguments` is a `serde_json::Value::Object` (the common case
-    /// that was previously broken because `Value::Object.as_str()` returns None).
-    #[test]
-    fn test_destructive_command_extraction_from_object_args() {
-        let arguments = serde_json::json!({"command": "rm -rf /tmp/stuff"});
-
-        let cmd = arguments
-            .get("command")
-            .and_then(|c| c.as_str().map(String::from))
-            .or_else(|| {
-                arguments
-                    .as_str()
-                    .and_then(|s| serde_json::from_str::<serde_json::Value>(s).ok())
-                    .and_then(|v| v.get("command").and_then(|c| c.as_str().map(String::from)))
-            });
-
-        assert_eq!(cmd.as_deref(), Some("rm -rf /tmp/stuff"));
-        assert!(requires_explicit_approval(cmd.as_deref().unwrap()));
-    }
-
-    /// Verify extraction still works when `arguments` is a JSON string
-    /// (rare, but possible if the LLM provider returns string-encoded JSON).
-    #[test]
-    fn test_destructive_command_extraction_from_string_args() {
-        let arguments =
-            serde_json::Value::String(r#"{"command": "git push --force origin main"}"#.to_string());
-
-        let cmd = arguments
-            .get("command")
-            .and_then(|c| c.as_str().map(String::from))
-            .or_else(|| {
-                arguments
-                    .as_str()
-                    .and_then(|s| serde_json::from_str::<serde_json::Value>(s).ok())
-                    .and_then(|v| v.get("command").and_then(|c| c.as_str().map(String::from)))
-            });
-
-        assert_eq!(cmd.as_deref(), Some("git push --force origin main"));
-        assert!(requires_explicit_approval(cmd.as_deref().unwrap()));
-    }
-
-    #[test]
-    fn test_requires_approval_for_destructive_command() {
-        let tool = ShellTool::new();
-        // Destructive commands must return true even though shell already
-        // requires base approval -- the distinction matters for auto-approve override.
-        assert!(tool.requires_approval_for(&serde_json::json!({"command": "rm -rf /tmp"})));
-        assert!(tool.requires_approval_for(
-            &serde_json::json!({"command": "git push --force origin main"})
-        ));
-        assert!(tool.requires_approval_for(&serde_json::json!({"command": "DROP TABLE users;"})));
-    }
-
-    #[test]
-    fn test_requires_approval_for_safe_command() {
-        let tool = ShellTool::new();
-        // Safe commands should not override auto-approval; only destructive ones do.
-        assert!(!tool.requires_approval_for(&serde_json::json!({"command": "cargo build"})));
-        assert!(!tool.requires_approval_for(&serde_json::json!({"command": "echo hello"})));
-    }
-
-    #[test]
-    fn test_requires_approval_for_string_encoded_args() {
-        let tool = ShellTool::new();
-        // When arguments are string-encoded JSON (rare LLM behavior).
-        let args = serde_json::Value::String(r#"{"command": "rm -rf /tmp/stuff"}"#.to_string());
-        assert!(tool.requires_approval_for(&args));
-    }
-
     #[test]
     fn test_sandbox_policy_builder() {
         let tool = ShellTool::new()

src/tools/builtin/taskrabbit.rs

@@ -0,0 +1,157 @@
+//! TaskRabbit tool for real-world task delegation.
+
+use async_trait::async_trait;
+use rust_decimal::Decimal;
+
+use crate::context::JobContext;
+use crate::tools::tool::{Tool, ToolError, ToolOutput};
+
+/// Tool for delegating real-world tasks via TaskRabbit.
+pub struct TaskRabbitTool {
+    // TODO: Add TaskRabbit API client
+}
+
+impl TaskRabbitTool {
+    /// Create a new TaskRabbit tool.
+    pub fn new() -> Self {
+        Self {}
+    }
+}
+
+impl Default for TaskRabbitTool {
+    fn default() -> Self {
+        Self::new()
+    }
+}
+
+#[async_trait]
+impl Tool for TaskRabbitTool {
+    fn name(&self) -> &str {
+        "taskrabbit"
+    }
+
+    fn description(&self) -> &str {
+        "Delegate real-world tasks to TaskRabbit taskers (delivery, assembly, cleaning, etc.)."
+    }
+
+    fn parameters_schema(&self) -> serde_json::Value {
+        serde_json::json!({
+            "type": "object",
+            "properties": {
+                "action": {
+                    "type": "string",
+                    "enum": ["search_taskers", "get_quote", "book_task", "get_status", "cancel_task"],
+                    "description": "The TaskRabbit action to perform"
+                },
+                "task_type": {
+                    "type": "string",
+                    "enum": ["delivery", "assembly", "moving", "cleaning", "handyman", "other"],
+                    "description": "Type of task"
+                },
+                "description": {
+                    "type": "string",
+                    "description": "Detailed description of the task"
+                },
+                "location": {
+                    "type": "object",
+                    "properties": {
+                        "address": { "type": "string" },
+                        "city": { "type": "string" },
+                        "state": { "type": "string" },
+                        "zip": { "type": "string" }
+                    },
+                    "description": "Location for the task"
+                },
+                "scheduled_time": {
+                    "type": "string",
+                    "description": "ISO 8601 datetime for when the task should be performed"
+                },
+                "budget": {
+                    "type": "number",
+                    "description": "Maximum budget for the task in USD"
+                },
+                "task_id": {
+                    "type": "string",
+                    "description": "Task ID (for get_status, cancel_task)"
+                }
+            },
+            "required": ["action"]
+        })
+    }
+
+    async fn execute(
+        &self,
+        params: serde_json::Value,
+        _ctx: &JobContext,
+    ) -> Result<ToolOutput, ToolError> {
+        let start = std::time::Instant::now();
+
+        let action = params
+            .get("action")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| {
+                ToolError::InvalidParameters("missing 'action' parameter".to_string())
+            })?;
+
+        // TODO: Implement actual TaskRabbit API integration
+        let result = match action {
+            "search_taskers" => {
+                serde_json::json!({
+                    "taskers": [],
+                    "message": "TaskRabbit integration not yet implemented"
+                })
+            }
+            "get_quote" => {
+                serde_json::json!({
+                    "quotes": [],
+                    "message": "TaskRabbit integration not yet implemented"
+                })
+            }
+            "book_task" => {
+                serde_json::json!({
+                    "booked": false,
+                    "message": "TaskRabbit integration not yet implemented"
+                })
+            }
+            "get_status" => {
+                let task_id = params.get("task_id").and_then(|v| v.as_str());
+
+                serde_json::json!({
+                    "task_id": task_id,
+                    "status": "unknown",
+                    "message": "TaskRabbit integration not yet implemented"
+                })
+            }
+            "cancel_task" => {
+                serde_json::json!({
+                    "cancelled": false,
+                    "message": "TaskRabbit integration not yet implemented"
+                })
+            }
+            _ => {
+                return Err(ToolError::InvalidParameters(format!(
+                    "unknown action: {}",
+                    action
+                )));
+            }
+        };
+
+        Ok(ToolOutput::success(result, start.elapsed()))
+    }
+
+    fn estimated_cost(&self, params: &serde_json::Value) -> Option<Decimal> {
+        // Booking a task has associated costs
+        if params.get("action").and_then(|v| v.as_str()) == Some("book_task") {
+            params
+                .get("budget")
+                .and_then(|v| v.as_f64())
+                .map(|b| Decimal::try_from(b).unwrap_or_default())
+        } else {
+            None
+        }
+    }
+
+    fn requires_sanitization(&self) -> bool {
+        true // External TaskRabbit data
+    }
+}

src/tools/builtin/time.rs

@@ -4,7 +4,7 @@ use async_trait::async_trait;
 use chrono::{DateTime, Utc};
 
 use crate::context::JobContext;
-use crate::tools::tool::{Tool, ToolError, ToolOutput, require_str};
+use crate::tools::tool::{Tool, ToolError, ToolOutput};
 
 /// Tool for getting current time and date operations.
 pub struct TimeTool;
@@ -52,7 +52,12 @@ impl Tool for TimeTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let operation = require_str(&params, "operation")?;
+        let operation = params
+            .get("operation")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| {
+                ToolError::InvalidParameters("missing 'operation' parameter".to_string())
+            })?;
 
         let result = match operation {
             "now" => {
@@ -64,7 +69,12 @@ impl Tool for TimeTool {
                 })
             }
             "parse" => {
-                let timestamp = require_str(&params, "timestamp")?;
+                let timestamp = params
+                    .get("timestamp")
+                    .and_then(|v| v.as_str())
+                    .ok_or_else(|| {
+                        ToolError::InvalidParameters("missing 'timestamp' parameter".to_string())
+                    })?;
 
                 let dt: DateTime<Utc> = timestamp.parse().map_err(|e| {
                     ToolError::InvalidParameters(format!("invalid timestamp: {}", e))
@@ -77,9 +87,19 @@ impl Tool for TimeTool {
                 })
             }
             "diff" => {
-                let ts1 = require_str(&params, "timestamp")?;
+                let ts1 = params
+                    .get("timestamp")
+                    .and_then(|v| v.as_str())
+                    .ok_or_else(|| {
+                        ToolError::InvalidParameters("missing 'timestamp' parameter".to_string())
+                    })?;
 
-                let ts2 = require_str(&params, "timestamp2")?;
+                let ts2 = params
+                    .get("timestamp2")
+                    .and_then(|v| v.as_str())
+                    .ok_or_else(|| {
+                        ToolError::InvalidParameters("missing 'timestamp2' parameter".to_string())
+                    })?;
 
                 let dt1: DateTime<Utc> = ts1.parse().map_err(|e| {
                     ToolError::InvalidParameters(format!("invalid timestamp: {}", e))