compress-session

name

compress-session

description

Distill the current conversation into a structured note (decisions made, open questions, file pointers with line numbers, next 1–3 actions) and save to `quality_reports/session_logs/` before auto-compression. Differs from `$checkpoint` (explicit stop-point snapshot) and from auto-compaction (which truncates rather than distills). Use when context is approaching auto-compact threshold, when a long pipeline has accumulated many decisions, or when the user says "compress", "distil this session", "before we hit auto-compact", "structured handoff before context resets".

$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

	$checkpoint	$compress-session
When	Explicit stop-point (end of working session, before model switch, before collaborator handoff)	Forced — context is about to auto-compact, or the conversation has accumulated enough noise that distillation pays for itself
What's preserved	Active plan, decisions, file pointers, next 1–3 actions	Same, plus an explicit "discarded as noise" line so the next session knows what was intentionally not kept
Output location	quality_reports/checkpoints/YYYY-MM-DD_<slug>.md	quality_reports/session_logs/YYYY-MM-DD_compression_<slug>.md
Triggering	User-invoked at a natural pause	User-invoked when context fatigue shows, OR proposed via PreCompact hook
Memory updates	Optional auto-proposal of [LEARN] entries	Always proposes [LEARN] entries — distillation is exactly the moment when generalizable lessons surface

Both skills are companions to the narrative session-log workflow at quality_reports/session_logs/. 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 hook triggered. The hook can call $compress-session automatically if the user has wired it in.

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

Read the most recent session log under quality_reports/session_logs/. If none exists, treat the current conversation as the source.

Optionally use <input> as a topic slug for the output filename.

Step 2: Distil into structured sections

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]
 ...



 [Question].  [Yes/No].  [pointer].
 ...



 [Specific next step with file pointer]
 ...



Things explored during this session that should NOT carry forward — failed hypotheses, abandoned approaches, debugging dead-ends. Listing them explicitly defends against []() (hallucinated / wrong content from early turns getting quoted later).

 [Hypothesis / approach / dead-end] — [why it didn't work]
 ...



Lessons worth promoting to MEMORY.md (or personal-memory.md if machine-specific). User reviews; nothing auto-merged.

  .  .
 ...

Step 3: Save

Write to quality_reports/session_logs/YYYY-MM-DD_compression_<topic>.md (slug derived from <input> 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 — that's $promote-memory's job.

Pairing with PreCompact hook

Forkers who want automatic compression can wire $compress-session into the PreCompact hook:

{
  "hooks": {
    "PreCompact": [{
      "hooks": [{
        "type": "command",
        "command": "echo 'Run $compress-session before compacting' && exit 2",
        "timeout": 5
      }]
    }]
  }
}

The hook surfaces a reminder; the user runs $compress-session manually. 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 quality_reports/session_logs/YYYY-MM-DD_compression_<topic>.md (gitignored — session-state, not version-controlled).
• Summary in the conversation: counts + HIGH-impact [LEARN] proposals.
• No file edits outside the compression file.