feat(projman): add checkpoint/resume for interrupted agent work (#237)

Executor checkpointing:
- Standard checkpoint comment format with branch, commit, phase
- Files modified with status (created, modified)
- Completed and pending steps tracking
- State notes for resumption context
- Save checkpoint after major steps, before stopping

Orchestrator resume detection:
- Scan issue comments for "## Checkpoint" markers
- Offer resume options: resume, start fresh, review details
- Verify branch exists and files match before resuming
- Dispatch executor with checkpoint context

Sprint-start integration:
- Checkpoint detection as first workflow step
- Resume flow documentation with example
- Checkpoint format specification

This enables resuming work after:
- Budget exhaustion (100 tool call limit)
- Agent failure/circuit breaker
- Manual interruption
- Session timeout

Closes #237

Co-Authored-By: Claude Opus 4.5 <noreply@anthropic.com>

plugins/projman/agents/executor.md

@@ -424,6 +424,81 @@ As the executor, you interact with MCP tools for status updates:
 - Apply best practices
 - Deliver quality work
 
+## Checkpointing (Save Progress for Resume)
+
+**CRITICAL: Save checkpoints so work can be resumed if interrupted.**
+
+**Checkpoint Comment Format:**
+```markdown
+## Checkpoint
+**Branch:** feat/45-jwt-service
+**Commit:** abc123 (or "uncommitted")
+**Phase:** [current phase]
+**Tool Calls:** 45
+
+### Files Modified
+- auth/jwt_service.py (created)
+- tests/test_jwt.py (created)
+
+### Completed Steps
+- [x] Created jwt_service.py skeleton
+- [x] Implemented generate_token()
+- [x] Implemented verify_token()
+
+### Pending Steps
+- [ ] Write unit tests
+- [ ] Add token refresh logic
+- [ ] Commit and push
+
+### State Notes
+[Any important context for resumption]
+```
+
+**When to Save Checkpoints:**
+- After completing each major step (every 20-30 tool calls)
+- Before stopping due to budget limit
+- When encountering a blocker
+- After any commit
+
+**Checkpoint Example:**
+```
+add_comment(
+    issue_number=45,
+    body="""## Checkpoint
+**Branch:** feat/45-jwt-service
+**Commit:** uncommitted (changes staged)
+**Phase:** Testing
+**Tool Calls:** 67
+
+### Files Modified
+- auth/jwt_service.py (created, 120 lines)
+- auth/__init__.py (modified, added import)
+- tests/test_jwt.py (created, 50 lines, incomplete)
+
+### Completed Steps
+- [x] Created auth/jwt_service.py
+- [x] Implemented generate_token() with HS256
+- [x] Implemented verify_token()
+- [x] Updated auth/__init__.py exports
+
+### Pending Steps
+- [ ] Complete test_jwt.py (5 tests remaining)
+- [ ] Add token refresh logic
+- [ ] Commit changes
+- [ ] Push to remote
+
+### State Notes
+- Using PyJWT 2.8.0
+- Secret key from JWT_SECRET env var
+- Tests use pytest fixtures in conftest.py
+"""
+)
+```
+
+**Checkpoint on Interruption:**
+
+If you must stop (budget, failure, blocker), ALWAYS post a checkpoint FIRST.
+
 ## Runaway Detection (Self-Monitoring)
 
 **CRITICAL: Monitor yourself to prevent infinite loops and wasted resources.**

plugins/projman/agents/orchestrator.md

@@ -93,7 +93,44 @@ git branch --show-current
 
 **Workflow:**
 
-**A. Fetch Sprint Issues**
+**A. Fetch Sprint Issues and Detect Checkpoints**
+```
+list_issues(state="open", labels=["sprint-current"])
+```
+
+**For each open issue, check for checkpoint comments:**
+```
+get_issue(issue_number=45)  # Comments included
+→ Look for comments containing "## Checkpoint"
+```
+
+**If Checkpoint Found:**
+```
+Checkpoint Detected for #45
+
+Found checkpoint from previous session:
+  Branch: feat/45-jwt-service
+  Phase: Testing
+  Tool Calls: 67
+  Files Modified: 3
+  Completed: 4/7 steps
+
+Options:
+1. Resume from checkpoint (recommended)
+2. Start fresh (discard previous work)
+3. Review checkpoint details first
+
+Would you like to resume?
+```
+
+**Resume Protocol:**
+1. Verify branch exists: `git branch -a | grep feat/45-jwt-service`
+2. Switch to branch: `git checkout feat/45-jwt-service`
+3. Verify files match checkpoint
+4. Dispatch executor with checkpoint context
+5. Executor continues from pending steps
+
+**B. Fetch Sprint Issues (Standard)**
 ```
 list_issues(state="open", labels=["sprint-current"])
 ```

plugins/projman/commands/sprint-start.md

@@ -25,7 +25,12 @@ If you are on a production or staging branch, you MUST stop and ask the user to
 
 The orchestrator agent will:
 
-1. **Fetch Sprint Issues**
+1. **Detect Checkpoints (Resume Support)**
+   - Check each open issue for `## Checkpoint` comments
+   - If checkpoint found, offer to resume from that point
+   - Resume preserves: branch, completed work, pending steps
+
+2. **Fetch Sprint Issues**
    - Use `list_issues` to fetch open issues for the sprint
    - Identify priorities based on labels (Priority/Critical, Priority/High, etc.)
 
@@ -300,6 +305,61 @@ Batch 2 (now unblocked):
 Starting #46 while #48 continues...
 ```
 
+## Checkpoint Resume Support
+
+If a previous session was interrupted (agent stopped, failure, budget exhausted), checkpoints enable resumption.
+
+**Checkpoint Detection:**
+The orchestrator scans issue comments for `## Checkpoint` markers containing:
+- Branch name
+- Last commit hash
+- Completed/pending steps
+- Files modified
+
+**Resume Flow:**
+```
+User: /sprint-start
+
+Orchestrator: Checking for checkpoints...
+
+Found checkpoint for #45 (JWT service):
+  Branch: feat/45-jwt-service
+  Last activity: 2 hours ago
+  Progress: 4/7 steps completed
+  Pending: Write tests, add refresh, commit
+
+Options:
+  1. Resume from checkpoint (recommended)
+  2. Start fresh (lose previous work)
+  3. Review checkpoint details
+
+User: 1
+
+Orchestrator: Resuming #45 from checkpoint...
+  ✓ Branch exists
+  ✓ Files match checkpoint
+  ✓ Dispatching executor with context
+
+Executor continues from pending steps...
+```
+
+**Checkpoint Format:**
+Executors save checkpoints after major steps:
+```markdown
+## Checkpoint
+**Branch:** feat/45-jwt-service
+**Commit:** abc123
+**Phase:** Testing
+
+### Completed Steps
+- [x] Step 1
+- [x] Step 2
+
+### Pending Steps
+- [ ] Step 3
+- [ ] Step 4
+```
+
 ## Getting Started
 
 Simply invoke `/sprint-start` and the orchestrator will: