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+# Delegation Cycle 1 — Retrospective
+
+## Date: 2026-03-15
+## Orchestrator: Hermes
+## Implementer: Kimi (kimi-k2.5, Moonshot servers)
+
+---
+
+## Tasks Attempted
+
+| Task | Issue | Branch | Status | Outcome |
+|------|-------|--------|--------|---------|
+| Decompose _maybe_distill() | #151 | refactor/151-maybe-distill | ✅ PR #160 | Clean first-pass, 1426 tests pass |
+| SQLite context managers | #148 | fix/148-sqlite-context-managers | ❌ Deferred | Kimi timed out 3x, changes lost to /tmp cleanup |
+
+## What Worked
+
+**#151 was a perfect Kimi task:**
+- Single file (thinking.py), clear decomposition target
+- Specific "done when" criteria (under 30 lines, tests pass)
+- Kimi produced clean code on first pass
+- Constants moved to module level, helpers well-named
+- 1426 tests pass, no behavior change
+- Total time: ~2 minutes for Kimi, ~5 minutes for review+commit+PR
+
+**The two-attempt rule:**
+- Applied correctly — after Kimi's second timeout on #148, I took over
+- Prevented infinite retry loops
+
+## What Failed
+
+**#148 was too large for Kimi:**
+- 22 call sites across 16 files
+- Kimi converted ~11 files on first pass but missed several
+- Timed out at 300s on second pass
+- Third attempt also timed out
+- Changes lost when /tmp worktrees were cleaned by macOS
+
+**Worktree location mistake:**
+- Initially created worktrees in /tmp/
+- macOS cleaned them between terminal calls
+- Lost Kimi's partial work (17 files, -800/+705 lines)
+- Fixed: moved worktrees to ~/worktrees/ (persistent)
+
+**Kimi's timeout pattern:**
+- Kimi spends significant time reading files and planning
+- On large tasks (16+ files), planning alone can exceed 300s
+- The --print flag doesn't give progress visibility
+- No way to tell if Kimi is stuck vs working
+
+## Metrics
+
+| Metric | Value |
+|--------|-------|
+| Tasks dispatched | 2 |
+| Tasks completed (PR created) | 1 |
+| Tasks deferred | 1 |
+| First-pass acceptance rate | 50% (1/2) |
+| Kimi invocations | 4 (1 for #151, 3 for #148) |
+| Total Kimi time | ~12 min (2 + 5 + 5 + timeout) |
+| Tests run | 3x (1426 pass each) |
+| Lines changed (accepted) | +127 / -95 |
+
+## Lessons Learned
+
+1. **Task size matters enormously.** #151 (1 file, 109 lines) was perfect. #148 (16 files, 22 call sites) was too big. Kimi's sweet spot is confirmed: 1-3 files, <150 lines of diff.
+
+2. **Split big tasks.** #148 should have been split into 4-5 sub-tasks of 3-4 files each. "Convert sqlite connections in timmy/" as one task, "dashboard/" as another, etc.
+
+3. **Never use /tmp for worktrees.** macOS cleans /tmp aggressively. Use ~/worktrees/ instead.
+
+4. **Kimi doesn't commit reliably.** Even when told to commit, it may not. Always verify with git log after Kimi runs. Commit on behalf of Kimi if the work is good.
+
+5. **Timeout of 300s is borderline.** For 3+ file tasks, 300s may not be enough. Consider 600s for medium tasks. But the real fix is smaller tasks, not bigger timeouts.
+
+6. **The two-attempt rule works.** It prevented me from burning 3+ cycles on a task that needed restructuring, not retrying.
+
+## Changes for Cycle 2
+
+- [ ] Split #148 into 4 sub-tasks by directory
+- [ ] Use ~/worktrees/ exclusively (never /tmp)
+- [ ] Set 180s timeout for small tasks, 300s for medium
+- [ ] Always verify Kimi committed before moving on
+- [ ] Commit Kimi's work immediately even if incomplete
+
+## Deliverables
+
+- PR #160: refactor: decompose _maybe_distill() into focused helpers (#151)
+  - Branch: refactor/151-maybe-distill
+  - Tests: 1426 pass, 76% coverage
+  - Ready to merge