Thread Context — Context Manager Auto-Save Upgrade

Where Things Stand

All skill work is complete. Two .skill files are packaged and ready for Brian to install. Workspace health passes 18/18. CLAUDE.md has been strengthened. GLOBAL.md has strategic priorities. The project README has both roadmaps (6-phase infra + 4-phase app build). The next step is creating a Phase 1 technical spec for CreativeOS in a new session.

Key Artifacts

Artifact	Location	Purpose
Context-manager skill (source)	rootphi-core/skills-source/context-manager/SKILL.md	Editable source with auto-save, checkpoint, artifact registry, session metrics, doc nudge, workspace-health gate
Context-manager skill (package)	rootphi-core/context-manager.skill	Installable package, final version
Workspace-health script (source)	rootphi-core/skills-source/workspace-health/scripts/check.py	Fixed script path resolution for skill-relative paths
Workspace-health skill (package)	rootphi-core/workspace-health.skill	Installable package with fix
Triangulation chat bundle	claude-context/chats/2026-03-27_creativeos-architecture-triangulation/	Backfilled — SUMMARY.md, THREAD.md, both artifact files
Architecture synthesis	rootphi-core/creativeos-architecture-synthesis_2026-03-27.md	Primary CreativeOS architecture deliverable (canonical copy)
Triangulation brief	rootphi-core/creativeos-triangulation-brief_2026-03-27.md	The 4 questions and context sent to all 7 providers
GLOBAL.md	claude-context/GLOBAL.md	Updated with strategic priorities, vision, 5-tier priority stack
Project README	claude-context/projects/rootphi-core/README.md	Two-roadmap structure: 6-phase infra readiness + 4-phase app build
CLAUDE.md	.claude/CLAUDE.md	Strengthened workspace-health instructions (mandatory, not optional)

What a Future Session Needs to Know

1. Two .skill files need installation: context-manager.skill and workspace-health.skill in the rootphi-core folder.
2. The triangulator skill still needs repackaging — stale Together AI key and old gemini-2.5-flash config in the installed copy. Source-of-truth configs are in rootphi-core/skills-source/llm-triangulator/config/.
3. The n8n test workflow (Uc6zEvGL7fI5MeI0 "Test Webhook Simple") should be cleaned up.
4. The next major work item is a Phase 1 technical spec for CreativeOS — use the write-spec or architecture skill, referencing the architecture synthesis document.
5. Context-manager now includes a documentation nudge in its checkpoint flow — when significant decisions are captured, it suggests formal docs (ADR, spec, runbook) via the appropriate engineering/product skill. This is new and hasn't been tested live yet.
6. Workspace-health is now embedded as a mandatory save gate in context-manager's checkpoint and session-end flows. If skills were modified, it runs before the save completes.
7. The 6-phase Infrastructure Readiness Roadmap was recovered from a condensed transcript and persisted. The phases are: (1) Ecosystem Audit & Architecture Design, (2) Security & Credential Hardening, (3) Quality Assurance Layer, (4) Stabilize & Lock, (5) Documentation & Portability, (6) Extend. See the project README for details.
8. Two distinct roadmaps exist: the 6-phase infra readiness roadmap (what phase we're in NOW — Phase 1 largely done) and the 4-phase CreativeOS application build plan (Foundation → Canvas+Intelligence → Knowledge+Scale → Productization). They're complementary, not competing.

Strategic Decisions — CreativeOS Build Approach

Brian asked about the big picture transition from skill infrastructure to actually building CreativeOS. Here's what was decided:

No custom documentation skill needed. The existing plugin skills cover CreativeOS's documentation needs: - engineering:documentation — READMEs, runbooks, onboarding guides, technical docs - engineering:architecture — ADRs (Architecture Decision Records) with trade-offs - product-management:write-spec — Feature specs and PRDs with goals, non-goals, acceptance criteria A custom skill would only make sense later if a specific doc pattern emerges that these don't handle.

Spec before code. The architecture synthesis captures what was decided and why, but not the implementation details needed to start coding — database schemas, project structure, environment variables, deployment configs, acceptance criteria. A Phase 1 technical spec bridges that gap.

Documentation nudge pattern. Brian asked when context saves should escalate to formal documentation. Answer: context-manager now proactively suggests it during checkpoints when the captured content warrants it. This bridges the gap between informal context (SUMMARY.md, THREAD.md) and formal engineering docs (ADRs, specs, runbooks). The nudge maps decision types to specific skills: - Architecture decisions → engineering:architecture (ADR) - System design / schemas → engineering:system-design - Feature scope / acceptance criteria → product-management:write-spec (PRD) - Operational procedures → engineering:documentation (runbook)

Phase 1 scope (from consensus architecture): - Postgres + Supabase setup (with RLS and tenant_id from day one per 7-provider consensus) - Next.js scaffold with module boundaries (modular monolith pattern) - Basic auth via Supabase Auth - Creative project CRUD model - Weeks 1-4 in the 5-phase roadmap

New sessions should start fresh. Long sessions risk context condensation. The context-manager skill (with auto-save + checkpoint now built in) handles handoff between sessions. The prompt for the Phase 1 spec session:

Pick up where I left off on CreativeOS. The architecture decisions are made and the full 6-phase infrastructure readiness roadmap is documented — see the project README at claude-context/projects/rootphi-core/README.md and the architecture synthesis at rootphi-core/creativeos-architecture-synthesis_2026-03-27.md. We're in Phase 1 (Ecosystem Audit & Architecture Design). The audit is largely done — the next deliverable is a Phase 1 technical spec that turns the consensus architecture into an actionable build plan. Phase 1 of the app build is "Foundation" (Weeks 1-4): Postgres + Supabase setup, Next.js scaffold, basic auth, creative project CRUD, with RLS and tenant_id from day one. Use the write-spec or architecture skill — whichever produces a better implementation-ready document. Reference the synthesis document for all consensus scores and rationale. Also note: there are two .skill files to install first — rootphi-core/context-manager.skill and rootphi-core/workspace-health.skill.

Pending Items

• Install context-manager.skill and workspace-health.skill
• Repackage triangulator skill with correct Together AI key and gemini-2.5-pro config
• Clean up n8n test workflow
• Create Phase 1 technical spec (new session, use prompt above)