| Not a git repository | git log returns "not a git repository" or exit code 128 | Use stat for file modification timestamps. Cross-reference with filesystem dates only; note in output that timeline correlation is approximate. |
| Git history unavailable | git log shows only "Initial commit" or empty output | Proceed with file timestamp analysis. Set staleness threshold to 14 days instead of 7 due to lower precision. |
| No documentation files found | find returns empty for all doc patterns | Report "No documentation surface found" and suggest creating README.md and AGENTS.md. Provide template structure based on detected project type. |
| Doc references non-existent files | Link check identifies broken internal references | Flag as "orphaned reference" in checklist. Suggest removal if target has no replacement, or correction if replacement file exists with different name. Never invent replacement targets. |
| Massive change scope | >50 commits or >20 files changed since last doc update | Split by directory. Produce separate analysis for each major module (e.g., src/, api/, docs/). Present module-by-module handoff checklist with per-module prioritization. |
| Missing milestone context | User provides no ticket ID, date range, or PR reference | Ask: "What milestone or date range should I analyze for documentation updates?" Accept responses like "since last Monday", "after PR #123", or "ticket PROJ-456". Wait for answer before proceeding. |
| Source directory ambiguity | Cannot determine which source dirs relate to which docs | Use directory proximity: docs in root apply to all source dirs; docs in docs/ apply to adjacent src/ or root source files; docs in module folders apply only to that module. Document assumption in output. |
| All docs already current | No stale docs detected | Report "Documentation surface current" with inventory table showing all files marked current. List the most recent 5 commits that were analyzed to demonstrate coverage. |
| START-HERE sections incomplete | Cannot determine architecture or next steps from codebase | Mark sections as "TBD - requires maintainer input" in output. Do not invent architecture diagrams or future plans not evidenced by issues, TODOs, or roadmap files in the repo. |