Session Documentation Enforcer

This skill ensures comprehensive documentation is created as part of completing work, preventing documentation debt and context loss between sessions.

Purpose

Without proactive documentation:

This skill treats documentation as part of "done" - not an afterthought.

When to Activate

Activate this skill automatically when:

1. **Feature implementation completed** - Any new capability has been added

2. **Bug fix committed** - Any issue has been resolved

3. **Significant code changes made** - More than trivial edits

4. **Session ending** - User says "done", "finished", or "ending session"

5. **Handoff requested** - User asks for summary, handoff, or status

6. **PR ready** - Before creating a pull request

Instructions

Step 1: Detect Completion Trigger

Monitor for these signals:

Step 2: Generate Required Documentation

Create documentation with ALL of these sections:

#### Minimum Required Sections

**What Was Done**

**Why It Was Done**

**How to Verify**

**What Remains**

#### Additional Sections (when applicable)

**Decisions Made**

**Gotchas and Warnings**

**Related Updates**

Step 3: For Session Handoffs (Required at Session End)

Create a comprehensive handoff document with:

**Current State**

**Completed This Session**

**Blocked Items**

**Next Steps (Prioritized)**

1. Highest priority task

2. Second priority task

3. Third priority task

**Verification Commands**

```bash

Specific commands to verify current state

Include expected output

```

**Key Files**

| File | Purpose |

|------|---------|

| path/to/file | Clear description of role |

Step 4: Quality Checklist

Before considering documentation complete, verify:

**Structure**

**Content**

**Completeness**

Step 5: Output to Appropriate Location

Place documentation in the correct location:

| Type | Location | Example Use Case |

|------|----------|------------------|

| Session handoff | `docs/development/SESSION_HANDOFF_YYYYMMDD.md` | Ending a work session |

| Feature docs | `docs/architecture/` or `docs/guides/` | New capability added |

| Bug fix notes | Commit message + CHANGELOG | Issue resolution |

| Technical details | `docs/development/` | Implementation specifics |

| Postmortem | `docs/development/POSTMORTEM_*.md` | Session analysis |

Examples

Anti-Pattern (Don't Do This)

```

"Fixed the bug in scheduler.py"

```

Correct Pattern (Do This)

```markdown

Bug Fix: Scheduler Timezone Mismatch

What Was Done

Files Modified

How to Verify

```bash

pytest backend/tests/test_scheduler.py::test_hst_conversion -v

Expected: 1 passed in 0.23s

```

Root Cause

Scheduler assumed UTC timestamps but database stored local time in HST timezone,

causing 10-hour scheduling offset for Hawaii-based users.

What Remains

```

Constraints

Success Criteria

Documentation is complete when:

1. All required sections are present with substantive content

2. Another developer could continue the work without asking questions

3. Verification commands successfully prove the work functions

4. Future sessions won't need to rebuild context from scratch

5. The documentation passes the quality checklist

Related Skills

This skill integrates with:

Notes

Remember: Documentation is not optional polish - it's how future sessions (including your own) avoid starting from zero. The time invested in documentation now saves multiples of that time in context rebuilding later.