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Context Manager Auto-Save Upgrade

Overview

Continued from the CreativeOS architecture triangulation session. Added automatic periodic saving and manual "checkpoint" trigger to the context-manager skill — Brian's key request to protect against context window condensation losing high-fidelity details during long sessions.

Key Decisions

  • Dual-trigger auto-save system: Two independent triggers, either of which fires a save:
  • Content-based: After 3+ save-worthy events (decisions, files, config changes, completed analyses)
  • Cadence-based: Every 10 substantive exchanges (configurable via "set auto-save cadence to N")
  • Manual checkpoint: "checkpoint" / "save checkpoint" / "save progress" / "snapshot this" forces an immediate thorough save — more comprehensive than auto-save (also updates GLOBAL.md, project READMEs, includes checkpoint markers)
  • Auto-save is invisible; checkpoints are confirmed: Auto-saves happen during natural pauses without interrupting flow. Checkpoints give explicit confirmation of what was captured.
  • Default cadence of 10 exchanges: Calibrated for 2-3 auto-saves before condensation risk in typical long sessions (30-50 exchanges). Adjustable per-session: lower (5-7) for high-stakes, higher (15-20) for casual.
  • Full-fidelity principle for checkpoints: When Brian says "checkpoint," preserve exact numbers, config values, rationale — the details that condensation strips away.

Checkpoint — 2026-03-27 Context Manager Upgrade Complete

  • Updated context-manager SKILL.md with auto-save + checkpoint features
  • Created skills-source copy at rootphi-core/skills-source/context-manager/SKILL.md
  • Packaged to rootphi-core/context-manager.skill (validation passed, 1024-char description limit met)
  • Workspace health: 15/16 passing (1 pre-existing flag: scripts/query_models.py path in CLAUDE.md)

Checkpoint — Round 2 improvements

Second round of improvements added: - Required "Key Artifacts" table in THREAD.md template (prevents orphaned deliverables) - Session Metrics logging in SUMMARY.md (auto-save cadence feedback loop) - Fixed workspace-health script to resolve skill-relative paths (scripts-exist now 18/18) - Backfilled missing triangulation session chat bundle with full SUMMARY.md, THREAD.md, and both artifact files

Checkpoint — Round 3 (documentation nudge, workspace-health gate, roadmap recovery)

Third round of improvements — driven by Brian's questions about when context saves should trigger formal documentation and why workspace-health wasn't running reliably: - Documentation nudge: Added to checkpoint flow — when a checkpoint captures significant architecture decisions, system design choices, or strategic direction, the skill now suggests producing a formal document using the appropriate engineering/product skill (ADR, spec, runbook, etc.) - Workspace-health as a save gate: Embedded as a mandatory step in both checkpoint and session-end flows inside context-manager SKILL.md. If any skill was modified since the last health check, it runs before the save completes. This is structural, not just a CLAUDE.md reminder. - CLAUDE.md strengthened: "After Skill Changes" section rewritten as "MANDATORY, NOT OPTIONAL" with explicit instructions. Prose description replaces inline script path (which was causing a false positive in workspace-health's script-reference checker). - 6-phase Infrastructure Readiness Roadmap recovered: Brian's original roadmap (Audit → Security → QA → Stabilize → Document → Extend) was lost to condensation in the prior session. Recovered from transcript and persisted to claude-context/projects/rootphi-core/README.md alongside the 4-phase CreativeOS Application Build Plan. - Strategic priorities added to GLOBAL.md: Full vision statement (rootphi-core as foundation for CreativeOS), 5-tier priority stack, and ADHD/Star Method principle about chunking work into satisfying completable units. - All skill files repackaged (context-manager.skill and workspace-health.skill) with final versions.

Action Items

  • [done] Design auto-save + checkpoint features
  • [done] Implement in SKILL.md (dual-trigger system, checkpoint commands, cadence config)
  • [done] Package updated skill (context-manager.skill)
  • [done] Run workspace-health check (18/18 passing after fix)
  • [done] Add Key Artifacts template requirement to THREAD.md
  • [done] Add session metrics logging to session-end save
  • [done] Fix workspace-health script path resolution for skill-relative paths
  • [done] Backfill triangulation session chat bundle
  • [done] Add documentation nudge to checkpoint flow
  • [done] Embed workspace-health as mandatory save gate in context-manager
  • [done] Strengthen CLAUDE.md workspace-health instructions (MANDATORY, NOT OPTIONAL)
  • [done] Recover 6-phase Infrastructure Readiness Roadmap to project README
  • [done] Add strategic priorities section to GLOBAL.md
  • [done] Rewrite CLAUDE.md to avoid false positive on inline script path
  • [pending] Brian to install updated context-manager.skill and workspace-health.skill
  • [pending] Repackage triangulator skill (stale Together AI key, old gemini-2.5-flash config)
  • [pending] Clean up test workflow in n8n (Uc6zEvGL7fI5MeI0)
  • [next] Create Phase 1 technical spec for CreativeOS (new session)

Files Created/Modified

  • rootphi-core/skills-source/context-manager/SKILL.md — Final skill with auto-save, checkpoint, artifact registry, session metrics, documentation nudge, workspace-health gate
  • rootphi-core/context-manager.skill — Packaged skill (final, with all improvements)
  • rootphi-core/skills-source/workspace-health/scripts/check.py — Fixed script path resolution
  • rootphi-core/workspace-health.skill — Packaged skill with fix
  • claude-context/chats/2026-03-27_creativeos-architecture-triangulation/ — Backfilled chat bundle
  • claude-context/GLOBAL.md — Added Strategic Priorities section (vision, 5-tier stack, ADHD principle)
  • claude-context/projects/rootphi-core/README.md — Two-roadmap structure (6-phase infra + 4-phase app build)
  • .claude/CLAUDE.md — Strengthened workspace-health instructions, removed false-positive-causing inline path

Session Metrics

  • Auto-saves triggered: 0 (session predates the feature — this was the session that built it)
  • Manual checkpoints: 3 (1 mid-session test, 1 round-2, 1 round-3/session-end)
  • Auto-save cadence: N/A (default 10, not yet active)

Tags: context-manager, skill-upgrade, auto-save, checkpoint, workspace-health, infrastructure, documentation-nudge, roadmap-recovery