diff --git a/.github/labeler.yml b/.github/labeler.yml
new file mode 100644
index 00000000..fd7da0be
--- /dev/null
+++ b/.github/labeler.yml
@@ -0,0 +1,166 @@
+# Scope labels for actions/labeler@v6
+# Maps file path globs to scope labels. Multiple labels can apply per PR.
+
+"scope: agent":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/agent/**
+
+"scope: channel":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/channels/channel.rs
+          - src/channels/manager.rs
+          - src/channels/mod.rs
+
+"scope: channel/cli":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/channels/cli/**
+          - src/cli/**
+
+"scope: channel/web":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/channels/web/**
+
+"scope: channel/wasm":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/channels/wasm/**
+
+"scope: tool":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/tools/tool.rs
+          - src/tools/registry.rs
+          - src/tools/mod.rs
+          - src/tools/sandbox.rs
+
+"scope: tool/builtin":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/tools/builtin/**
+
+"scope: tool/wasm":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/tools/wasm/**
+
+"scope: tool/mcp":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/tools/mcp/**
+
+"scope: tool/builder":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/tools/builder/**
+
+"scope: db":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/db/mod.rs
+
+"scope: db/postgres":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/db/postgres.rs
+          - migrations/**
+
+"scope: db/libsql":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/db/libsql_backend.rs
+          - src/db/libsql_migrations.rs
+
+"scope: safety":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/safety/**
+
+"scope: llm":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/llm/**
+
+"scope: workspace":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/workspace/**
+
+"scope: orchestrator":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/orchestrator/**
+
+"scope: worker":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/worker/**
+
+"scope: secrets":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/secrets/**
+
+"scope: config":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/config.rs
+          - src/settings.rs
+
+"scope: extensions":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/extensions/**
+
+"scope: setup":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/setup/**
+
+"scope: evaluation":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/evaluation/**
+
+"scope: estimation":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/estimation/**
+
+"scope: sandbox":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/sandbox/**
+          - Dockerfile*
+
+"scope: hooks":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/hooks/**
+
+"scope: pairing":
+  - changed-files:
+      - any-glob-to-any-file:
+          - src/pairing/**
+
+"scope: ci":
+  - changed-files:
+      - any-glob-to-any-file:
+          - .github/workflows/**
+          - .github/scripts/**
+
+"scope: docs":
+  - changed-files:
+      - any-glob-to-any-file:
+          - "**/*.md"
+          - docs/**
+          - LICENSE*
+
+"scope: dependencies":
+  - changed-files:
+      - any-glob-to-any-file:
+          - Cargo.toml
+          - Cargo.lock
diff --git a/.github/scripts/create-labels.sh b/.github/scripts/create-labels.sh
new file mode 100755
index 00000000..8386fae4
--- /dev/null
+++ b/.github/scripts/create-labels.sh
@@ -0,0 +1,71 @@
+#!/usr/bin/env bash
+# Idempotent label bootstrap for IronClaw PR automation.
+# Uses `gh label create --force` so it can be re-run safely.
+#
+# Usage: bash .github/scripts/create-labels.sh
+# Requires: gh CLI authenticated with repo scope
+
+set -euo pipefail
+
+if ! command -v gh &>/dev/null; then
+  echo "Error: gh CLI is required. Install from https://cli.github.com" >&2
+  exit 1
+fi
+
+create() {
+  local name="$1" color="$2" description="$3"
+  gh label create "$name" --color "$color" --description "$description" --force
+}
+
+echo "==> Creating size labels..."
+create "size: XS"    "F9D0C4" "< 10 changed lines (excluding docs)"
+create "size: S"     "F5A3A3" "10-49 changed lines"
+create "size: M"     "E57373" "50-199 changed lines"
+create "size: L"     "D32F2F" "200-499 changed lines"
+create "size: XL"    "B71C1C" "500+ changed lines"
+
+echo "==> Creating risk labels..."
+create "risk: low"    "4CAF50" "Changes to docs, tests, or low-risk modules"
+create "risk: medium" "FFC107" "Business logic, config, or moderate-risk modules"
+create "risk: high"   "F44336" "Safety, secrets, auth, or critical infrastructure"
+create "risk: manual" "9E9E9E" "Risk level set manually (sticky, not overwritten)"
+
+echo "==> Creating scope labels..."
+create "scope: agent"         "006B75" "Agent core (agent loop, router, scheduler)"
+create "scope: channel"       "00838F" "Channel infrastructure"
+create "scope: channel/cli"   "00897B" "TUI / CLI channel"
+create "scope: channel/web"   "00796B" "Web gateway channel"
+create "scope: channel/wasm"  "00695C" "WASM channel runtime"
+create "scope: tool"          "1565C0" "Tool infrastructure"
+create "scope: tool/builtin"  "1976D2" "Built-in tools"
+create "scope: tool/wasm"     "1E88E5" "WASM tool sandbox"
+create "scope: tool/mcp"      "2196F3" "MCP client"
+create "scope: tool/builder"  "42A5F5" "Dynamic tool builder"
+create "scope: db"            "4A148C" "Database trait / abstraction"
+create "scope: db/postgres"   "6A1B9A" "PostgreSQL backend"
+create "scope: db/libsql"     "7B1FA2" "libSQL / Turso backend"
+create "scope: safety"        "880E4F" "Prompt injection defense"
+create "scope: llm"           "4527A0" "LLM integration"
+create "scope: workspace"     "283593" "Persistent memory / workspace"
+create "scope: orchestrator"  "0D47A1" "Container orchestrator"
+create "scope: worker"        "01579B" "Container worker"
+create "scope: secrets"       "BF360C" "Secrets management"
+create "scope: config"        "E65100" "Configuration"
+create "scope: extensions"    "33691E" "Extension management"
+create "scope: setup"         "827717" "Onboarding / setup"
+create "scope: evaluation"    "558B2F" "Success evaluation"
+create "scope: estimation"    "9E9D24" "Cost/time estimation"
+create "scope: sandbox"       "00BFA5" "Docker sandbox"
+create "scope: hooks"         "6D4C41" "Git/event hooks"
+create "scope: pairing"       "4E342E" "Pairing mode"
+create "scope: ci"            "546E7A" "CI/CD workflows"
+create "scope: docs"          "78909C" "Documentation"
+create "scope: dependencies"  "90A4AE" "Dependency updates"
+
+echo "==> Creating contributor labels..."
+create "contributor: new"         "FFF9C4" "First-time contributor"
+create "contributor: regular"     "FFE082" "2-5 merged PRs"
+create "contributor: experienced" "FFB74D" "6-19 merged PRs"
+create "contributor: core"        "FF8A65" "20+ merged PRs"
+
+echo "Done. All labels created/updated."
diff --git a/.github/scripts/pr-labeler.sh b/.github/scripts/pr-labeler.sh
new file mode 100755
index 00000000..96dc0fa7
--- /dev/null
+++ b/.github/scripts/pr-labeler.sh
@@ -0,0 +1,139 @@
+#!/usr/bin/env bash
+# Classify a PR by size, risk, and contributor tier.
+# Called by the pr-label-classify workflow.
+#
+# Inputs (env vars):
+#   PR_NUMBER  — pull request number
+#   REPO       — owner/repo (e.g. "user/ironclaw")
+#
+# Requires: gh CLI, jq
+
+set -euo pipefail
+
+PR_NUMBER="${PR_NUMBER:?PR_NUMBER is required}"
+REPO="${REPO:?REPO is required}"
+
+# ─── helpers ────────────────────────────────────────────────────────────────
+
+# Remove all labels in a dimension except the desired one.
+# Usage: set_exclusive_label "size" "size: M"
+set_exclusive_label() {
+  local prefix="$1" desired="$2"
+
+  # Fetch current labels on the PR
+  local current
+  current=$(gh pr view "$PR_NUMBER" --repo "$REPO" --json labels --jq '.labels[].name')
+
+  # Remove any existing label with the same prefix
+  while IFS= read -r label; do
+    [[ -z "$label" ]] && continue
+    if [[ "$label" == "${prefix}:"* && "$label" != "$desired" ]]; then
+      gh pr edit "$PR_NUMBER" --repo "$REPO" --remove-label "$label" 2>/dev/null || true
+    fi
+  done <<< "$current"
+
+  # Add the desired label
+  gh pr edit "$PR_NUMBER" --repo "$REPO" --add-label "$desired"
+}
+
+# ─── size ───────────────────────────────────────────────────────────────────
+
+classify_size() {
+  # Sum changed lines across non-doc files
+  local total
+  total=$(gh api "repos/${REPO}/pulls/${PR_NUMBER}/files" \
+    --paginate --jq '
+      [.[] | select(.filename | test("\\.(md|txt|rst|adoc)$") | not) | .changes]
+      | add // 0
+    ')
+
+  local label
+  if   (( total < 10 ));  then label="size: XS"
+  elif (( total < 50 ));  then label="size: S"
+  elif (( total < 200 )); then label="size: M"
+  elif (( total < 500 )); then label="size: L"
+  else                         label="size: XL"
+  fi
+
+  echo "Size: ${total} changed lines -> ${label}"
+  set_exclusive_label "size" "$label"
+}
+
+# ─── risk ───────────────────────────────────────────────────────────────────
+
+classify_risk() {
+  # If "risk: manual" is present, skip — it's a sticky override
+  local current
+  current=$(gh pr view "$PR_NUMBER" --repo "$REPO" --json labels --jq '.labels[].name')
+  if echo "$current" | grep -qx "risk: manual"; then
+    echo "Risk: skipped (manual override)"
+    return
+  fi
+
+  # Fetch changed file paths
+  local files
+  files=$(gh api "repos/${REPO}/pulls/${PR_NUMBER}/files" \
+    --paginate --jq '.[].filename')
+
+  local risk="low"
+
+  while IFS= read -r file; do
+    [[ -z "$file" ]] && continue
+
+    case "$file" in
+      # High risk: safety, secrets, auth, crypto, setup, orchestrator auth
+      src/safety/*|src/secrets/*|src/llm/session.rs|src/orchestrator/auth.rs|\
+      src/channels/web/auth.rs|src/setup/*)
+        risk="high"
+        break  # can't go higher
+        ;;
+
+      # Medium risk: agent core, config, database, worker, tools, channels
+      src/agent/*|src/config.rs|src/settings.rs|src/db/*|src/worker/*|\
+      src/tools/*|src/channels/*|src/orchestrator/*|src/context/*|\
+      src/hooks/*|src/sandbox/*|src/extensions/*|Cargo.toml|\
+      .github/workflows/*)
+        # Only upgrade, never downgrade
+        [[ "$risk" != "high" ]] && risk="medium"
+        ;;
+
+      # Low risk: docs, tests, estimation, evaluation, history, etc.
+      *)
+        ;;
+    esac
+  done <<< "$files"
+
+  echo "Risk: ${risk}"
+  set_exclusive_label "risk" "risk: ${risk}"
+}
+
+# ─── contributor tier ───────────────────────────────────────────────────────
+
+classify_contributor() {
+  # Get PR author
+  local author
+  author=$(gh pr view "$PR_NUMBER" --repo "$REPO" --json author --jq '.author.login')
+
+  # Count merged PRs by this author in this repo
+  local count
+  count=$(gh pr list --repo "$REPO" --state merged --author "$author" \
+    --limit 100 --json number --jq 'length')
+
+  local label
+  if   (( count == 0 )); then label="contributor: new"
+  elif (( count < 6 ));  then label="contributor: regular"
+  elif (( count < 20 )); then label="contributor: experienced"
+  else                        label="contributor: core"
+  fi
+
+  echo "Contributor: ${author} has ${count} merged PRs -> ${label}"
+  set_exclusive_label "contributor" "$label"
+}
+
+# ─── main ───────────────────────────────────────────────────────────────────
+
+echo "Classifying PR #${PR_NUMBER} in ${REPO}..."
+classify_size
+classify_risk
+classify_contributor
+echo "Done."
diff --git a/.github/workflows/pr-label-classify.yml b/.github/workflows/pr-label-classify.yml
new file mode 100644
index 00000000..90f141de
--- /dev/null
+++ b/.github/workflows/pr-label-classify.yml
@@ -0,0 +1,26 @@
+name: "PR: Classify (Size, Risk, Contributor)"
+
+on:
+  pull_request_target:
+    types: [opened, synchronize, reopened]
+
+permissions:
+  contents: read
+  pull-requests: write
+  issues: read           # needed for search/issues API (contributor count)
+
+jobs:
+  classify:
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout base branch
+        uses: actions/checkout@v4
+        with:
+          ref: ${{ github.event.pull_request.base.ref }}
+
+      - name: Classify PR
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+          PR_NUMBER: ${{ github.event.pull_request.number }}
+          REPO: ${{ github.repository }}
+        run: bash .github/scripts/pr-labeler.sh
diff --git a/.github/workflows/pr-label-scope.yml b/.github/workflows/pr-label-scope.yml
new file mode 100644
index 00000000..1c388561
--- /dev/null
+++ b/.github/workflows/pr-label-scope.yml
@@ -0,0 +1,18 @@
+name: "PR: Scope Labels"
+
+on:
+  pull_request_target:
+    types: [opened, synchronize, reopened]
+
+permissions:
+  contents: read
+  pull-requests: write
+
+jobs:
+  scope:
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/labeler@v5
+        with:
+          configuration-path: .github/labeler.yml
+          sync-labels: false          # additive only — never remove scope labels