---
phase: 01.4-enrich-checkpoint-workflow
plan: 01
subsystem: session-handoff
tags: [context-lifecycle, checkpoint-protocol, multi-session, work-log, handoff]

requires:
  - "Phase 1.3: Context lifecycle pattern (checkpoint → clear → resume)"
  - "Phase 1.3: Checkpoint vs promotion separation"
  - "OG GSD pause-work pattern (Current Understanding section)"

provides:
  - "WORK.md template with Current Understanding section (30-second resume)"
  - "Type-tagged session log structure ([VISION], [DECISION], [PLAN], [EXEC], [BLOCKER])"
  - "Checkpoint workflow instructions for maintaining Current Understanding"

affects:
  - "Phase 1.5: Evaluation framework will test fresh agent resume capability"
  - "Future single-agent sessions: Agents use enriched WORK.md for cross-session work"

tech-stack:
  added: []
  patterns:
    - "Current Understanding section (OG GSD pause-work adaptation)"
    - "Type-tagged session log entries for non-linear access"
    - "Hybrid narrative+log structure"

key-files:
  created: []
  modified:
    - src/gsd_lite/template/WORK.md
    - src/gsd_lite/template/workflows/checkpoint.md

decisions:
  - id: "DECISION-01.4-01"
    summary: "Current Understanding structure uses 5 XML sections from OG GSD pause-work"
    rationale: "Proven pattern enables 30-second fresh agent resume without re-reading full log"
    alternatives: ["Custom JSON format", "Free-form narrative"]
    date: "2026-01-25"

  - id: "DECISION-01.4-02"
    summary: "WORK.md semantic broadened from 'execution log' to 'session work log'"
    rationale: "Supports all workflow modes (moodboard, whiteboard, execution) not just execution"
    alternatives: ["Keep execution-only semantic", "Separate logs per mode"]
    date: "2026-01-25"

  - id: "DECISION-01.4-03"
    summary: "Type-tagged entries with 5 tags: [VISION], [DECISION], [PLAN], [EXEC], [BLOCKER]"
    rationale: "Enables grep-based querying for specific work type; supports non-linear access"
    alternatives: ["Free-form entries", "Structured JSON entries"]
    date: "2026-01-25"

  - id: "DECISION-01.4-04"
    summary: "Update Current Understanding at checkpoint time, not every turn"
    rationale: "Prevents mid-session update churn; Current Understanding syncs at handoff boundary"
    alternatives: ["Update every turn", "Update only on user request"]
    date: "2026-01-25"

metrics:
  duration: "2 min 50 sec"
  completed: "2026-01-25"
---

# Phase 1.4 Plan 01: Enrich WORK.md and Checkpoint Workflow Summary

**One-liner:** Current Understanding section + type-tagged session log enable fresh agent resume in 30 seconds for multi-session work

## What Was Built

### 1. WORK.md Template Enrichment

**Added Current Understanding section:**
- Five XML parts: `<current_state>`, `<vision>`, `<decisions>`, `<blockers>`, `<next_action>`
- Follows OG GSD pause-work pattern for handoff state
- Target: Fresh agent reads in 30 seconds and resumes work seamlessly
- Positioned at top of file before chronological log

**Broadened semantic from "execution log" to "session work log":**
- Supports all workflow modes: moodboard (vision), whiteboard (planning), execution (action)
- Header comment explains lifecycle: created at phase start, updated every turn, deleted after promotion
- Clarifies distinction from STATE.md (HOW vs WHERE)

**Implemented type-tagged session log:**
- Five entry types with semantic tags:
  - `[VISION]` - User vision/preferences extracted, references
  - `[DECISION]` - Decisions with rationale and alternatives considered
  - `[PLAN]` - Task breakdown, risk identification, approach
  - `[EXEC]` - Files modified, commands run, execution work
  - `[BLOCKER]` - Open questions, waiting states, stuck items
- Entry format: timestamp + tag + description + details (3-8 lines max)
- Examples show concrete content demonstrating each tag type
- Inline comments explain when/how to use structure

### 2. Checkpoint Workflow Enhancement

**Added Step 2: Update Current Understanding in WORK.md:**
- Instructs agents to update Current Understanding at checkpoint time
- Documents what to update in each of the five XML sections
- Provides before/after example showing stale vs current state
- Key principles: concrete facts (not jargon), avoid prior context references, 30-second readability

**Updated Checkpoint vs Promotion table:**
- Added row: "Current Understanding | Updated to end-of-session state | N/A (WORK.md deleted)"
- Reinforces checkpoint preserves WORK.md, promotion trims it

**Added Common Pitfalls:**
- Current Understanding drift (update at checkpoint, not mid-session)
- Jargon in Current Understanding (use concrete examples, fresh agent has zero context)

## Technical Implementation

**WORK.md template structure:**
```
1. Header comment (SESSION WORK LOG semantic, lifecycle, purpose, distinction)
2. Ephemeral warning
3. Current Understanding section (5 XML parts with inline guidance)
4. Horizontal rule separator
5. Session Log (Chronological) with type-tagged entries
6. Examples for each tag type
```

**checkpoint.md workflow structure:**
```
Step 1: Update STATE.md (unchanged)
Step 2: Update Current Understanding in WORK.md (NEW)
  - Five sections to update
  - Before/after example
  - Key principles
Step 3: Preserve WORK.md (added note about Current Understanding)
Step 4: Capture Loops (unchanged)
Step 5: Confirm Resume Ready (unchanged)
```

**Line counts:**
- WORK.md: 142 lines (meets 80+ minimum)
- checkpoint.md: 445 lines (meets 300+ minimum)

## Deviations from Plan

None - plan executed exactly as written.

## Decisions Made

### DECISION-01.4-01: Current Understanding Structure

**Context:** Need handoff section for fresh agent resume.

**Decision:** Use 5 XML sections from OG GSD pause-work pattern.

**Rationale:** Proven pattern across OG GSD multi-day work. Structured enough for consistency, flexible enough for narrative content.

**Alternatives considered:**
1. Custom JSON format (more structured, less readable)
2. Free-form narrative (more flexible, harder to parse consistently)

**Impact:** Fresh agents have consistent structure to read. Template provides clear guidance on what goes in each section.

### DECISION-01.4-02: WORK.md Semantic Broadening

**Context:** Current "execution log" semantic doesn't fit moodboard/whiteboard modes.

**Decision:** Broaden to "session work log" capturing all work types.

**Rationale:** Phase 1.3 CONTEXT.md explicitly requested this broadening. All workflow modes need to log work naturally.

**Alternatives considered:**
1. Keep execution-only semantic (simpler, but excludes vision/planning work)
2. Separate logs per mode (more isolated, but fragments session continuity)

**Impact:** WORK.md now naturally accommodates vision extraction, planning discussions, execution work, and blockers in single chronological log.

### DECISION-01.4-03: Type-Tagged Entries

**Context:** Need to support non-linear access to session log.

**Decision:** Five tags: [VISION], [DECISION], [PLAN], [EXEC], [BLOCKER].

**Rationale:** Based on HANDOFF patterns from GSD_PATTERNS.md. Enables `grep "\[DECISION\]"` to find decision history without reading full log.

**Alternatives considered:**
1. Free-form entries (simpler to write, harder to query)
2. Structured JSON entries (machine-parseable, less readable for humans)

**Impact:** Agents can query specific work type. Fresh agents can scan for relevant information non-linearly.

### DECISION-01.4-04: Update Timing

**Context:** When should Current Understanding be updated?

**Decision:** At checkpoint time only, not every turn.

**Rationale:** Mid-session drift is acceptable; Current Understanding syncs at handoff boundary. Prevents update churn during active session.

**Alternatives considered:**
1. Update every turn (accurate but high overhead)
2. Update only on user request (lower overhead but may forget)

**Impact:** Checkpoint workflow explicitly instructs updating Current Understanding as Step 2. Fresh agents expect current state at resume time.

## Key Learnings

### 1. Concrete Examples Critical for Template Adoption

WORK.md template includes 8 concrete session log entries showing each tag type in use. Without these, agents wouldn't know what "good" entries look like.

### 2. Inline Guidance Prevents Cross-File Navigation

Every section has inline comments explaining when/how to use it. Prevents agents from having to read checkpoint.md to understand WORK.md structure.

### 3. Before/After Examples Clarify Anti-Patterns

checkpoint.md Step 2 includes stale vs current Current Understanding example. Shows exactly what "drift" looks like and how to fix it.

## Risks & Mitigations

**Risk:** Agents forget to update Current Understanding at checkpoint time.
**Mitigation:** checkpoint.md makes it Step 2 (before preserving WORK.md). Sticky note self-check includes Current Understanding update.

**Risk:** Agents use jargon in Current Understanding ("as discussed").
**Mitigation:** Inline comments explicitly warn against this. Pitfalls section documents anti-pattern.

**Risk:** Current Understanding becomes too long (>60 seconds to read).
**Mitigation:** RESEARCH.md Open Question #4 acknowledges this for complex multi-day phases. Accept 60s over compression.

## Next Phase Readiness

**Phase 1.5 (Evaluation Framework) can proceed immediately:**
- WORK.md template ready to test fresh agent resume
- Checkpoint workflow documents Current Understanding maintenance
- Type-tagged entries provide material for grep-based retrieval tests

**Success criteria for Phase 1.5:**
- Fresh agent reads Current Understanding and correctly resumes task
- Agent updates Current Understanding at checkpoint (not mid-session)
- Agent uses type tags consistently ([VISION], [DECISION], etc.)

**No blockers or concerns.**

## Verification

All success criteria met:

- [x] WORK.md template has Current Understanding section with 5 XML parts
- [x] WORK.md template has type-tagged session log format supporting all workflow modes
- [x] checkpoint.md instructs updating Current Understanding at checkpoint time
- [x] Fresh agent can read Current Understanding section and resume work in 30 seconds
- [x] All inline comments explain when/how to use new structures
- [x] No ASCII art introduced (markdown headers + mermaid only)
- [x] File sizes: WORK.md 142 lines (>80), checkpoint.md 445 lines (>300)

## Commits

| Task | Commit | Message |
|------|--------|---------|
| 1 | b945246 | feat(01.4-01): enrich WORK.md with Current Understanding and type-tagged session log |
| 2 | 21f1563 | feat(01.4-01): update checkpoint workflow with Current Understanding maintenance |

**Duration:** 2 min 50 sec
**Tasks completed:** 2/2

---

*Phase: 01.4-enrich-checkpoint-workflow*
*Plan: 01 of 02*
*Completed: 2026-01-25*
