config: record learning M224 - squash commits before approval

Enhanced warn-unsquashed-approval.sh hook to also detect when in main
workspace with related commits that should be squashed (implementation
+ STATE.md update pairs).

Prevention: Hook now warns when presenting approval with unsquashed
related commits, even after merging to base branch.

Author: cowwoc

.claude/cat/retrospectives/mistakes.json

@@ -2984,6 +2984,32 @@
         "catches_variations": true
       },
       "correct_behavior": "Use inner_width - 2 - len(content) for padding calculation to ensure all box lines have consistent width"
+    },
+    {
+      "id": "M224",
+      "timestamp": "2026-01-24T12:00:00Z",
+      "category": "protocol_violation",
+      "description": "Presented approval gate with unsquashed commits - implementation and parent STATE.md update were separate commits instead of squashed together",
+      "root_cause": "Merged to base branch then committed STATE.md update separately in main workspace, bypassing worktree commit squashing",
+      "rca_method": "C",
+      "rca_method_name": "causal-barrier",
+      "prevention_type": "hook",
+      "prevention_path": "${CLAUDE_PROJECT_DIR}/plugin/hooks/warn-unsquashed-approval.sh",
+      "pattern_keywords": [
+        "squash",
+        "approval",
+        "commits",
+        "STATE.md"
+      ],
+      "prevention_implemented": true,
+      "prevention_verified": false,
+      "recurrence_of": null,
+      "prevention_quality": {
+        "verification_type": "positive",
+        "fragility": "low",
+        "catches_variations": true
+      },
+      "correct_behavior": "Squash all related commits (implementation + STATE.md updates) into a single commit BEFORE presenting the approval gate to user"
     }
   ]
 }

.claude/cat/retrospectives/retrospectives.json

@@ -1,6 +1,6 @@
 {
   "last_retrospective": "2026-01-23T19:15:39-05:00",
-  "mistake_count_since_last": 0,
+  "mistake_count_since_last": 1,
   "config": {
     "mistake_count_threshold": 10,
     "trigger_interval_days": 7

plugin/hooks/warn-unsquashed-approval.sh

@@ -1,10 +1,12 @@
 #!/bin/bash
 # Hook: warn-unsquashed-approval.sh
 # Type: PreToolUse (AskUserQuestion)
-# Purpose: Warn when presenting approval gate with unsquashed commits (M199)
+# Purpose: Warn when presenting approval gate with unsquashed commits (M199/M224)
 #
 # This hook detects when an approval gate is being presented during /cat:work
 # and warns if commits haven't been squashed yet.
+#
+# M224: Also checks main workspace for recent task commits that should be squashed.
 
 set -euo pipefail
 
@@ -15,12 +17,6 @@ if [[ "$TOOL_NAME" != "AskUserQuestion" ]]; then
     exit 0
 fi
 
-# Check if we're in a task worktree
-if [[ ! -f "$(git rev-parse --git-dir 2>/dev/null)/cat-base" ]]; then
-    echo '{}'
-    exit 0
-fi
-
 # Get the tool input to check if this is an approval-related question
 TOOL_INPUT="${TOOL_INPUT:-}"
 
@@ -30,33 +26,35 @@ if ! echo "$TOOL_INPUT" | grep -qi "approve"; then
     exit 0
 fi
 
-# Get base branch from worktree metadata
-CAT_BASE_FILE="$(git rev-parse --git-dir)/cat-base"
-BASE_BRANCH=$(cat "$CAT_BASE_FILE" 2>/dev/null || echo "")
-
-if [[ -z "$BASE_BRANCH" ]]; then
-    echo '{}'
-    exit 0
-fi
-
-# Count commits on task branch
-COMMIT_COUNT=$(git rev-list --count "${BASE_BRANCH}..HEAD" 2>/dev/null || echo "0")
-
-# If more than 2 commits, warn about squashing
-if [[ "$COMMIT_COUNT" -gt 2 ]]; then
-    output_hook_message "PreToolUse" "$(cat << EOF
-⚠️ PRE-APPROVAL CHECK FAILED: UNSQUASHED COMMITS (M199)
-
-Found ${COMMIT_COUNT} commits on task branch (expected 1-2 after squashing).
-
-Commits on branch:
-$(git log --oneline "${BASE_BRANCH}..HEAD")
-
-BLOCKING: Run /cat:git-squash BEFORE presenting approval gate.
-Per work.md Pre-Approval Checklist, commits must be squashed by type first.
-EOF
-)"
-    exit 0
+# Check if we're in a task worktree
+CAT_BASE_FILE="$(git rev-parse --git-dir 2>/dev/null)/cat-base"
+if [[ -f "$CAT_BASE_FILE" ]]; then
+    # In worktree - check commits against base branch
+    BASE_BRANCH=$(cat "$CAT_BASE_FILE" 2>/dev/null || echo "")
+
+    if [[ -n "$BASE_BRANCH" ]]; then
+        COMMIT_COUNT=$(git rev-list --count "${BASE_BRANCH}..HEAD" 2>/dev/null || echo "0")
+
+        if [[ "$COMMIT_COUNT" -gt 2 ]]; then
+            echo "{\"additionalContext\": \"⚠️ PRE-APPROVAL CHECK FAILED: UNSQUASHED COMMITS (M199)\\n\\nFound ${COMMIT_COUNT} commits on task branch (expected 1-2 after squashing).\\n\\nBLOCKING: Run /cat:git-squash BEFORE presenting approval gate.\"}"
+            exit 0
+        fi
+    fi
+else
+    # M224: In main workspace - check for recent task commits that weren't squashed
+    # Look for multiple commits with same Task ID in last 5 commits
+    RECENT_COMMITS=$(git log --oneline -5 2>/dev/null || echo "")
+
+    # Check if last 2+ commits are related (same task or config/planning pair)
+    LAST_TWO=$(git log --oneline -2 2>/dev/null || echo "")
+    TASK_ID_COUNT=$(git log --format="%B" -5 2>/dev/null | grep -c "Task ID:" || echo "0")
+
+    # If we have a planning/config commit followed by a task commit, they should be squashed
+    if echo "$LAST_TWO" | head -1 | grep -qE "^[a-f0-9]+ (config|planning):.*progress" && \
+       echo "$LAST_TWO" | tail -1 | grep -qE "^[a-f0-9]+ (feature|bugfix|refactor|test|docs):"; then
+        echo "{\"additionalContext\": \"⚠️ PRE-APPROVAL CHECK: RELATED COMMITS SHOULD BE SQUASHED (M224)\\n\\nFound separate commits that should be combined:\\n$(echo \"$LAST_TWO\" | sed 's/^/  /')\\n\\nThe implementation commit and STATE.md update should be in the SAME commit.\\nSquash these commits before approval.\"}"
+        exit 0
+    fi
 fi
 
 echo '{}'