~cytrogen/gstack

ref: db35b8e5bffb596144c4c7f4a3b7eb5c078edaaf gstack/docs/designs/SESSION_INTELLIGENCE.md -rw-r--r-- 6.8 KiB
db35b8e5 — Garry Tan feat: session intelligence roadmap + design doc (#727) 8 days ago

#Session Intelligence Layer

#The Problem

Claude Code's context window is ephemeral. Every session starts fresh. When auto-compaction fires at ~167K tokens, it preserves a generic summary but destroys file reads, reasoning chains, and intermediate decisions.

gstack already produces valuable artifacts that survive on disk: CEO plans, eng reviews, design reviews, QA reports, learnings. These files contain decisions, constraints, and context that shaped the current work. But Claude doesn't know they exist. After compaction, the plans and reviews that informed every decision silently vanish from context.

The ecosystem is working on this. claude-mem (9K+ stars) captures tool usage and injects context into future sessions. Claude HUD shows real-time agent status. Anthropic's own claude-progress.txt pattern uses a progress file that agents read at the start of each session.

Nobody is solving the specific problem of making skill-produced artifacts survive compaction. Because nobody else has gstack's artifact architecture.

#The Insight

gstack already writes structured artifacts to ~/.gstack/projects/$SLUG/:

  • CEO plans: ceo-plans/
  • Design reviews: design-reviews/
  • Eng reviews: eng-reviews/
  • Learnings: learnings.jsonl
  • Skill usage: ../analytics/skill-usage.jsonl

The missing piece is not storage. It's awareness. The preamble needs to tell the agent: "These files exist. They contain decisions you've already made. After compaction, re-read them."

#The Architecture

                   ┌─────────────────────────────────────┐
                   │        Claude Context Window         │
                   │   (ephemeral, ~167K token limit)     │
                   │                                      │
                   │   Compaction fires ──► summary only   │
                   └──────────────┬──────────────────────┘
                                  │
                          reads on start / after compaction
                                  │
                   ┌──────────────▼──────────────────────┐
                   │    ~/.gstack/projects/$SLUG/         │
                   │    (persistent, survives everything) │
                   │                                      │
                   │  ceo-plans/         ← /plan-ceo-review
                   │  eng-reviews/       ← /plan-eng-review
                   │  design-reviews/    ← /plan-design-review
                   │  checkpoints/       ← /checkpoint (new)
                   │  timeline.jsonl     ← every skill (new)
                   │  learnings.jsonl    ← /learn
                   └─────────────────────────────────────┘
                                  │
                          rolled up weekly
                                  │
                   ┌──────────────▼──────────────────────┐
                   │           /retro                      │
                   │  Timeline: 3 /review, 2 /ship, ...   │
                   │  Health trends: compile 8/10 (↑2)     │
                   │  Learnings applied: 4 this week       │
                   └─────────────────────────────────────┘

#The Features

#Layer 1: Context Recovery (preamble, all skills)

~10 lines of prose in the preamble. After compaction or context degradation, the agent checks ~/.gstack/projects/$SLUG/ for recent plans, reviews, and checkpoints. Lists the directory, reads the most recent file.

Cost: near-zero. Benefit: every skill's plans/reviews survive compaction.

#Layer 2: Session Timeline (preamble, all skills)

Every skill appends a one-line JSONL entry to timeline.jsonl: timestamp, skill name, branch, key outcome. /retro renders it.

Makes the project's AI-assisted work history visible. "This week: 3 /review, 2 /ship, 1 /investigate across branches feature-auth and fix-billing."

#Layer 3: Cross-Session Injection (preamble, all skills)

When a new session starts on a branch with recent artifacts, the preamble prints a one-liner: "Last session: implemented JWT auth, 3/5 tasks done. Plan: ~/.gstack/projects/$SLUG/checkpoints/latest.md"

The agent knows where you left off before reading any files.

#Layer 4: /checkpoint (opt-in skill)

Manual snapshot of working state: what's being done, files being edited, decisions made, what's remaining. Useful before stepping away, before complex operations, for workspace handoffs, or coming back after days.

#Layer 5: /health (opt-in skill)

Code quality dashboard: type-check, lint, test suite, dead code scan. Composite 0-10 score. Tracks over time. /retro shows trends. /ship gates on configurable threshold.

#The Compounding Effect

Each feature is independently useful. Together, they create something that compounds:

Session 1: /plan-ceo-review produces a plan. Saved to disk. Session 2: Agent reads the plan after preamble. Doesn't re-ask decisions. Session 3: /checkpoint saves progress. Timeline shows 2 /review, 1 /ship. Session 4: Compaction fires mid-refactor. Agent re-reads the checkpoint. Recovers key decisions, types, remaining work. Continues. Session 5: /retro rolls up the week. Health trend: 6/10 → 8/10. Timeline shows 12 skill invocations across 3 branches.

The project's AI history is no longer ephemeral. It persists, compounds, and makes every future session smarter. That's the session intelligence layer.

#What This Is Not

  • Not a replacement for Claude's built-in compaction (that handles session state; we handle gstack artifacts)
  • Not a full memory system like claude-mem (that handles cross-session memory via SQLite; we handle structured skill artifacts)
  • Not a database or service (just markdown files on disk)

#Research Sources