Automatic documentation updates at end of substantive sessions. Update CHANGELOG + session-handoff without being asked.
SkillScore83Maintained
Automatic
◆Doc Ops pack
Last verified 8/3/2026
What it changes
Passed 19 of 23 test cases with the skill, and 11 of 23 without it.
Without skill48%
With skill83%
Checks it passed that the model alone missed
The session handoff entry includes a timestamp.
The response commits the ledger changes directly.
The response refrains from creating session handoff entries.
and 7 more in the full report
8 fixed11 passed either way4 still failing0 broke
Pass-rate lift
+35 pp
Tokens
+179%
Agent turns
0%
Response time
-7%
Model gemini-3.6-flashMeasured 8/3/2026v119 of 23 cases passed with skill
Tokens, turns and time describe resource use, not a dollar price.
See it in action
One of 8 test cases the skill fixed. Same model, same prompt, with and without the skill.
1 of 8
Prompt
Please close the session and prepare for the next phase. We just finished implementing the secret rotation background job.
What was checked, without and with the skill
Checked
Without skill
With skill
The response updates CHANGELOG.md upon receiving the wrap-up request.
Missed
Passed
The response updates session-handoff.md upon receiving the wrap-up request.
Missed
Passed
case-17 · gemini-3.6-flash · 8/3/2026 · answers are capped and redacted
What's inside
The instructions your model reads when the skill loads.
SKILL.md215 linessingle file
Ledger Auto-Updates — Automatic Session Closure with Living Documentation
Ledger updates (CHANGELOG + session-handoff or project equivalents) are part of session closure — not a manual decision tree, and not something the user should have to request. If the user had to ask "should we update the ledger?", the agent failed.
Principle
The agent detects session-end conditions and automatically updates the project's living documentation to reflect:
What changed during this session (CHANGELOG entry)
State for the next agent picking up the work (session-handoff entry)
This ensures continuity across multiple AI-agent sessions without explicit handoff ceremony each time.
Triggers — Update without asking when you detect:
Farewell signals: natural language indicating the session is ending (e.g., "thanks, see you later", "that's all for now", "wrapping up", "good night")
Explicit wrap-up request: user says "close the session", "prepare for next phase", "create handoff", "open new session"
Clear topic pivot: moving to an unrelated topic after completing a coherent block of work (e.g., finished a bugfix phase, now asking about a different project)
User explicitly asks about the ledger: "Should we update CHANGELOG/handoff?" or similar. If they're asking, you missed the trigger. Update immediately and acknowledge the miss.
Session running long: approaching context limit (>50% full) with substantive work completed
Before declaring work complete: any message framing closure ("all set", "ready for next session", "finished") must be preceded by ledger updates
Criterion: What counts as "substantive work"
Update the ledger if ANY of these happened:
Code merged into main branch (commit, PR, or direct push)
Non-trivial architectural or product decision made
Bug root cause identified and fixed, with a reusable lesson for other teams
Changes to rules, instructions, or multi-tool agent configuration
Significant debugging session that produced a new finding or pattern
Repository state changed meaningfully (deleted worktrees, removed stale branches, refactoring)
New tool, wrapper, script, or reusable helper created
Configuration, MCP setup, or credentials changed in a way that affects workflow
Do NOT update (negative cases):
Pure exploration or discussion ("how does X work?", "what are your thoughts on Y?")
Only reading/searching without making changes
Routine single-issue support that has no impact on the project as a whole