# Delegation Cycle 1 — Retrospective

## Date: 2026-03-15
## Orchestrator: Hermes
## Implementer: Kimi (kimi-k2.5, Moonshot servers)

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## 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