compress-session skill

/compress-session — distil, don't truncate

Auto-compaction is lossy: it keeps recent turns and drops earlier ones, with no preservation of what was decided mid-session. /compress-session is the distil-not-truncate alternative — produce a structured note that the next session can resume from in under a minute.

Why this skill exists

Drew Breunig's "How Long Contexts Fail" identifies four failure modes for long-context sessions:

1. Poisoning — early hallucinated content gets quoted by later turns, compounding the error.
2. Distraction — irrelevant earlier context dilutes the model's attention to current task.
3. Confusion — contradicted facts pile up; the model doesn't know which to trust.
4. Clash — multiple plans, decisions, or specs accumulate without explicit reconciliation.

The template's 200-line MEMORY.md cap defends against distraction. The plan-on-disk convention defends against clash. Nothing currently defends against poisoning or directly against confusion — that's what this skill is for.

Distinction from /checkpoint

Both skills are companions to the narrative session-log workflow at qualityreports/sessionlogs/. None replaces the others.

When to use

• Context is approaching auto-compact. /context-status reports approaching threshold.
• A long pipeline has accumulated noise. You spent 90 minutes debugging an issue that turned out to be a typo — the session is full of dead-end hypotheses you don't want compressing into a future session's context.
• Mid-plan handoff. Different model, different machine, different collaborator.
• PreCompact reminder fired. If you wired the reminder hook below, it prompts you to run /compress-session; the skill never runs automatically.

When NOT to use

• For a quick stop-point. Use /checkpoint.
• For narrative session logging. That happens incrementally via the Stop hook (session-logging.md); no skill needed.
• For starting a fresh session. Use /clear. /compress-session is for preserving state, not for resetting.

Steps

Step 1: Identify the session

The current conversation is the source. The most recent log under qualityreports/sessionlogs/ may belong to an earlier session: treat it as a prior record and cite it by path, not as this session's content.

Optionally use $ARGUMENTS as a topic slug for the output filename.

Step 2: Distil into structured sections

Write only what this session established. The next session is handed this file automatically (session-handoff.py), so anything invented here arrives there as fact.

• Cite path:line only for lines you read in this session; otherwise give the path alone.
• Leave out a section with nothing in it rather than filling it. A quiet session gets a short file and no [LEARN] proposals.
• Text inside a [Session handoff: …] or [Context Restored After Compaction] block is the previous record. Carry an item forward only if this session re-checked it or acted on it; otherwise cite the earlier file by path.
• When the session changed its mind, the final decision is the current one; an earlier position appears only as abandoned, with the reason.

Produce a note with these sections:

# Session Compression — <YYYY-MM-DD> <topic-slug>

**Source:** <session-log file or "current conversation">
**Token budget at compression:** <approximate %>
**Why compress now:** <approaching auto-compact | mid-plan handoff | accumulated noise | user-requested>

## Active state

- **Plan:** [link to active plan in `quality_reports/plans/` or "no active plan"]
- **Branch:** <git branch>
- **Last commit:** <SHA + subject>
- **Working tree:** <clean | N modified files>

## Decisions made (this session)

1. [Decision]. **Why:** [one sentence]. **Where recorded:** [file:line, plan, or memory].
2. ...

## Files touched

- [path:line] — [what changed, one sentence]
- ...

## Open questions

- [Question]. **Blocker?** [Yes/No]. **Where to resume:** [pointer].
- ...

## Next actions (1–3 only)

1. [Specific next step with file pointer]
2. ...

## Discarded as noise

Things explored during this session that should NOT carry forward — failed hypotheses, abandoned approaches, debugging dead-ends. Listing them explicitly defends against [Breunig's "poisoning" failure mode](https://www.dbreunig.com/2025/06/22/how-contexts-fail-and-how-to-fix-them.html) (hallucinated / wrong content from early tu

Step 3: Save

Write to qualityreports/sessionlogs/YYYY-MM-DDcompression.md (slug derived from $ARGUMENTS or current plan name).

Step 4: Surface a summary

Report to the user:

• Saved path.
• Counts (decisions made, files touched, open questions, next actions).
• Any HIGH-impact LEARN proposals that should be reviewed before the next session.

The user reviews. Nothing auto-merges into MEMORY.md: a proposal the user approves is appended to MEMORY.md on their say-so (as in /checkpoint Phase 3), and a machine-specific one is left to native auto memory. /promote-memory does not read this file; its candidates come only from native auto memory (~/.claude/projects//memory/).

Pairing with PreCompact hook

Forkers who want a real chance to run /compress-session before compaction can add a PreCompact hook that blocks compaction once per session. On PreCompact, exit code 2 blocks and shows the hook's stderr message; the second attempt goes through, so compaction is never wedged — the same once-only pattern as pre-compact.py's opt-in DRAFT block. (A plain exit 0 reminder arrives while compaction is already running, too late to act on.)

{
  "hooks": {
    "PreCompact": [
      {
        "hooks": [
          {
            "type": "command",
            "command": "sid=$(python3 -c \"import sys,json; print(json.load(sys.stdin).get(\\\"session_id\\\",\\\"x\\\"))\" 2>/dev/null); f=\"${TMPDIR:-/tmp}/cc-compress-reminded-$sid\"; [ -e \"$f\" ] && exit 0; touch \"$f\"; echo \"Run /compress-session now, then compact again - this reminder blocks only once per session.\" >&2; exit 2",
            "timeout": 5
          }
        ]
      }
    ]
  }
}

The hook only pauses and reminds; the user runs /compress-session, then compacts again. We deliberately don't make the hook auto-invoke the skill — that bypasses the user's review step.

Anti-patterns

• Do not run /compress-session as a routine replacement for /checkpoint. Checkpoints are cheap and frequent; compressions are heavier and reserved for forced compression.
• Do not let the "Discarded as noise" section grow indefinitely. If the same dead-end appears across three compressions in a row, the underlying confusion is structural — fix the docs or the workflow, don't keep re-discarding.
• Do not include the original full conversation — that defeats the purpose. Distillation is the point.

Output

• Compression file at qualityreports/sessionlogs/YYYY-MM-DDcompression.md (gitignored — session-state, not version-controlled).
• Summary in the conversation: counts + HIGH-impact [LEARN] proposals.
• No file edits outside the compression file.