Session Continuity Skill

Purpose

Conversations end. Context compresses. Sessions expire. Crashes happen. Sleep happens. Days pass. This skill maintains state across all of these boundaries through structured checkpoints that a future Claude instance can use to reconstitute accurately.

The Problem

Every conversation disruption loses state. Compaction summaries are lossy. New sessions start cold. The user has to re-explain context, re-establish rapport, and re-orient Claude to where they were. This friction compounds. Important threads get dropped. Nuance evaporates.

The problem isn't memory — it's continuity. Claude remembers facts. It doesn't remember where we were.

Checkpoint Protocol

When to Checkpoint

• Natural stopping points: End of a topic, shift in focus, user stepping away
• Before expected compaction: When context is getting long, create a checkpoint before it compresses
• End of session: Always checkpoint when a conversation is ending
• Before risky operations: Checkpoint the state before doing something that might fail
• On request: User says "checkpoint", "save state", "bookmark this"

Checkpoint Format

CHECKPOINT — [ISO-8601 timestamp]
SESSION: [thread identifier or slug]
PASS: [number if part of a transcript-chain]

WHERE WE ARE:
[1-3 sentences. What we're in the middle of. Not a summary — a location.]

WHAT WE DECIDED:
[Bulleted list of decisions made this session. Only decisions, not discussion.]

WHAT'S UNRESOLVED:
[Bulleted list of open questions, pending items, things we said we'd come back to.]

WHAT TO DO NEXT:
[The immediate next action if we were to continue right now.]

EMOTIONAL CONTEXT:
[One sentence. What's the tone/energy? Frustrated? Flowing? Exhausted? Excited?]

FILES TOUCHED:
[List of files read, edited, or created this session, if applicable.]

Checkpoint Storage

Write checkpoints to a persistent file:

~/Documents/Claude-Sessions/checkpoints.md

Append-only. Newest at bottom. Each checkpoint is a self-contained reconstitution point.

Reconstitution Protocol

When starting a new session or resuming after a gap:

1. Read checkpoints.md — find the most recent checkpoint
2. Read the WHERE WE ARE section — orient to the location in the work
3. Read WHAT'S UNRESOLVED — these are your entry points
4. Read EMOTIONAL CONTEXT — calibrate tone
5. Acknowledge the reconstitution naturally: "Picking up where we left off..." or similar
6. Do NOT re-summarize everything. The checkpoint carries the state. Just continue.

Multi-Day Gaps

For gaps longer than 24 hours:

• Read the last 2-3 checkpoints, not just the most recent
• Note the trajectory — what's the direction of the work across sessions?
• Ask one orienting question: "Last time we were working on X. Want to continue there or has something shifted?"

Integration with Other Skills

• transcript-chain: Checkpoints can serve as pass boundaries. A checkpoint at the end of a deep analysis session becomes the compaction summary for the next pass.
• temporal-spatial-proximity: The rhythm log captures conditions; checkpoints capture state. Together they provide full reconstitution — where we were AND the conditions under which we got there.
• coherency-audit: Run a coherency check after reconstitution from a long gap. Things may have changed while we were apart.

Setup

mkdir -p ~/Documents/Claude-Sessions
touch ~/Documents/Claude-Sessions/checkpoints.md

Critical Rules

1. Checkpoints are locations, not summaries. Write them as if you're dropping a pin, not writing a report.
2. UNRESOLVED items are the thread. They're what pulls the next session forward.
3. Emotional context matters. A session that ended in frustration reconstitutes differently than one that ended in flow.
4. Don't over-checkpoint. Natural stopping points only. Every message doesn't need a checkpoint.
5. The checkpoint is for the next Claude, not the current one. Write it for someone who has no other context.