Plan design docs release sync

Current — the latest status report. Reports freeze once published; corrections appear in later reports.

Design docs + code walkthroughs, release-time doc sync (background agents)

Context

The repo has frozen plans (the why), a generated roadmap (the what's next), and status reports (the what happened) — but no living description of the what is: architecture, data flow, and a guided tour of the code. Rick wants two new artifact kinds under docs/designs/, tied to releases, regenerated automatically at release time by background agents, plus release-time refresh of the user guide and README so shipped docs never drift from the shipped code. All of it publishes to the wiki via the existing ledger.

Artifact model (mirrors the roadmap-snapshot pattern)

Dated (frozen, publish-once — same rules as roadmap snapshots):

• docs/designs/<DATE>_<NAME>_design_doc.md
• docs/designs/<DATE>_<NAME>_code_walkthrough.md
• <NAME> at release time is vX.Y.Z-release (matches snapshot naming); ad-hoc names allowed mid-cycle.
• Frontmatter: date, name, tag: vX.Y.Z (git tag), roadmap_snapshot: docs/roadmap/<date>_<name>.md, git_hash, branch.

Current (live, regenerated each release — same rules as the live Roadmap page):

• docs/designs/current_design_doc.md, docs/designs/current_code_walkthrough.md
• Frontmatter: generated_at (UTC date-time), git_hash, branch, roadmap: docs/roadmap.md, tag (latest release tag when generated at release).
• Frozen-artifact exception documented: these two are the only docs besides docs/roadmap.md that get rewritten in place.

Content templates live in the skill dir as references:

• references/design-doc-prompt.md — Rick's full 35-section Design Document Prompt (supplied in-session), stored with these improvements:
  1. Sections are a menu, not a quota. New preamble: include only sections whose subject exists in the analyzed system; close the doc with an "Omitted sections" list, one line of reason each. (35 enterprise sections against a stdlib-only CLI would be mostly "N/A" padding — omission-with-reason keeps the doc honest AND short.)
  2. Vendor sections genericized. §16 Redis / §19 Bedrock become "for each cache/AI-provider dependency actually present…", keeping Rick's detailed checklists as the per-dependency template. §17 MCP / §18 AI endpoints keep their checklists, gated the same way.
  3. Source material auto-filled, not [insert]ed. The skill fills System Context/Source Material from the repo itself: README, spec, docs/plans/, docs/adr/, .work/config.yml, test suites — the analyzed repo is the source of truth, placeholders deleted.
  4. Source-reference + accuracy rules merged in from Rick's companion walkthrough prompt: every code claim cites path — function(), lines N–M; quote exactly; never invent; distinguish production/test/deprecated code; no secrets. Labels Confirmed/Assumption/Recommendation/Open Question kept.
  5. Frontmatter block required (this plan's artifact model: generated_at / git_hash / branch / tag / roadmap ref) — the prompt's own "store under docs/design/design_doc.md" line is replaced by our layout: docs/designs/<DATE>_<NAME>_design_doc.md (Rick's stated convention; the prompt's path/name-order variant normalized to it).
  6. Mermaid rules kept, plus our house constraint: node cap with "+K more" (no silent truncation), diagrams derived from actual code/events only.
  7. Quality-controls and Output-Rules sections kept verbatim (they're good); "Validate the Mermaid syntax" stays — we render Mermaid in the roadmap already, so broken syntax is visible immediately.
• references/code-walkthrough-prompt.md — walkthrough variant built from the same accuracy/source-reference rules: guided tour of bin/ + hooks/ + plugin/ in execution order, tests as executable spec, junior-engineer orientation (where to start, what's risky, which invariants must hold), gaps-and-drift section comparing walkthrough against the design doc — design doc as context, never as proof.

New skill: design-docs (repo .claude/skills/ + plugin copy, canon versioning)

Instructions, no shipped code (consistent with skill-based edges):

1. Read .work/config.yml release.sync_docs list (see below).
2. Generate = run the reference prompt against the ACTUAL repo at HEAD; stamp frontmatter from git rev-parse / git describe --tags / current roadmap.
3. Release mode: regenerate both current_* files, then freeze dated copies <DATE>_<vX.Y.Z-release>_*.md with tag + snapshot frontmatter.
4. Sync mode (ad-hoc): regenerate current_* only; dated copy only when asked.
5. Publish via wiki-publish: Design-Doc / Code-Walkthrough live pages (republish on hash change) + frozen dated pages linked from Home — ledger keys design/current-design-doc, design/<date>_<name>-design-doc, etc.
6. Always executed in a background subagent — same non-blocking rule as viz.

Config: the release-sync list (Rick: "a list … updated on release")

.work/config.yml gains:

release:
  sync_docs:            # regenerated by background agents at every release
    - design-doc        # docs/designs/current_design_doc.md + dated freeze
    - code-walkthrough  # docs/designs/current_code_walkthrough.md + dated freeze
    - user-guide        # docs/user_guide/*.md reviewed against diff since last tag
    - readme            # README.md same

Remove an entry to opt a doc out of release sync. plugin/scripts/init.sh scaffold gains the same block (commented defaults).

Release skill integration (the automation)

release skill (both copies) gains a step between "Tag and platform release" and "Publish and sync": spawn background agents, never block the tag:

• Agent A — design-docs skill in release mode (current + dated + wiki).
• Agent B — user-docs refresh: diff vPREV..vX.Y.Z, update docs/user_guide/* and README.md where the diff made them stale (guided by release.sync_docs), commit on main after the release lands, republish changed wiki pages via ledger.
• The release itself completes without waiting; agents report when done. Doc commits land AFTER the tag (docs describe the release; the tag doesn't wait for prose).

Files

• .claude/skills/design-docs/SKILL.md + references/{design-doc-prompt,code-walkthrough-prompt}.md
• plugin/skills/design-docs/ mirror (with version: frontmatter — lockstep test picks it up automatically)
• .claude/skills/release/SKILL.md + plugin/skills/release/SKILL.md — new background-agents step
• .work/config.yml + plugin/scripts/init.sh — release.sync_docs block
• docs/designs/ — first generation: current_* pair + dated v0.11.0-release pair against the just-cut tag (dogfood proof)
• .claude/skills/wiki-publish/SKILL.md (+ plugin) — one line adding designs to the default publish set; frozen/live rules already cover the rest
• docs/user_guide/user-guide.md, plugin-guide.md, README.md — document the new artifacts + release sync
• tests/test_plugin.py — skill count/version lockstep covers the new skill automatically (assertGreaterEqual); packaging guard unchanged (docs/ never ships)
• CLAUDE.md — one policy bullet: designs regenerate on release via background agents; current_* are the sanctioned rewrite-in-place exception; dated ones frozen

Execution shape

Wave 1 (parallel subagents): skill + references | release-skill step + config | docs updates. Wave 2 (background agent, dogfood): generate the four artifacts against v0.11.0 and publish to wiki. PR → green-gates loop → merge. Version stays 0.11.0 (content change post-release; next release picks it up — same pattern as the ADO-caveats PR).

Verification

• tests/test_plugin.py green (canon + lockstep + packaging).
• docs/designs/ holds 4 files; frontmatter carries tag/hash/branch/roadmap refs that match git rev-parse v0.11.0 and the v0.11.0 snapshot path.
• Wiki shows Design-Doc + Code-Walkthrough live pages + dated pages linked from Home; .work/published.json has the new keys.
• A re-run of the design-docs skill with unchanged sources publishes nothing (hash-skip proof).
• Release skill text: next release spawns the agents (proven live at v0.12.0).
• Plan captured via worklog plan-capture to docs/plans/ at execution start.

Tasks

• (P1) design-docs skill: SKILL.md + references/design-doc-prompt.md (Rick's 35-section prompt, improved) + references/code-walkthrough-prompt.md; plugin mirror with version frontmatter
• (P1) release skill gains background-agents doc-sync step (both copies); release.sync_docs list in .work/config.yml + init.sh scaffold
• (P1) docs: user guide + plugin guide + README document design artifacts; CLAUDE.md policy bullet; wiki-publish default set gains designs
• (P1) dogfood generation: current_design_doc + current_code_walkthrough + dated v0.11.0-release pair under docs/designs/ (background agent, grounded in actual repo, frontmatter tag/hash/branch/roadmap)
• (P1) wiki: Design-Doc + Code-Walkthrough live pages, frozen dated pages, Home links, published.json ledger keys
• (P2) suites green; PR; green-gates merge; item closeout