Session Continuity

How skills maintain context across sessions spanning days or weeks.

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The Problem

Creative and analytical work rarely completes in one sitting. You might brainstorm today, think overnight, and continue tomorrow. Traditional AI conversations lose context between sessions—you have to re-explain everything each time.

Session continuity solves this through versioned documents that capture the full state of work.

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How It Works

Versioned Documents

Each session produces a new version of the working document:

project-name/
├── _index.md           # Version history, decision log
├── project-name-v1.md  # Session 1 output
├── project-name-v2.md  # Session 2 output
├── project-name-v3.md  # Session 3 output
└── ...

When you return, you provide the latest version file. Claude reads it and picks up exactly where you left off.

What Gets Captured

Version documents typically include:

The Index File

A separate index file tracks the project across all versions:

# Project Index

## Version History

- v1 (Jan 15): Initial brainstorm, identified 3 directions
- v2 (Jan 18): Deep dive on direction A, parked B and C
- v3 (Jan 22): Refined direction A, ready for validation

## Major Decisions

1. Target reader is mid-career professionals (v2)
2. Focus on transformation, not information (v3)

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Session Patterns

Starting a New Session

You: Let's continue the productivity app brainstorm.

Claude: I'll need the latest version file to pick up where we left off.
        Can you share project-name-v3.md?

You: [uploads file]

Claude: Got it. Reading through v3...

        Last session (Jan 22), we refined the target reader to
        mid-career professionals and identified three key pain points.
        The overnight question was "Would you pay for this yourself?"

        How did that land? Ready to pick up there?

During a Session

Claude tracks the conversation and captures significant developments:

• When decisions crystallize
• When thinking shifts meaningfully
• When new questions emerge
• At natural breakpoints

Ending a Session

Every session concludes with:

1. Exit Summary — Current state, key decisions, open questions, next steps
2. The Overnight Test — A question to sit with before next session
3. Version Creation — New versioned document capturing everything

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Session Energy

Many skills ask about "session energy" at the start:

This lets the skill adapt to your available time and mental state.

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Multi-Week Projects

For projects spanning weeks:

Synthesis Documents

After 3+ sessions, skills may offer:

"We've had 5 sessions on this. Want me to create a synthesis document that distills our current best thinking?"

Synthesis documents consolidate learning without losing the version history.

Returning After a Break

If significant time has passed, Claude won't assume you remember the context:

Claude: Welcome back! It's been 12 days since our last session.
        Reading through v4, here's where things stand...
        [provides comprehensive status summary]

        Does this still feel current, or has your thinking shifted?

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Best Practices

Do

• Keep version files — The history matters; don't delete old versions
• Provide the latest version — Always share the most recent file when continuing
• Use the overnight test — Percolation between sessions often yields breakthroughs
• Let Claude summarize — The status recap catches you up and verifies shared understanding

Don't

• Overwrite files — Create new versions, don't modify old ones
• Skip the exit summary — This captures crucial context for next session
• Rush session endings — Proper closure enables proper continuation

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Technical Implementation

Skills implement continuity through:

1. Document Templates — Consistent structure for version files
2. Session Flow — Start/during/end patterns in SKILL.md
3. Status Checks — Questions at session start to orient
4. Update Triggers — When to capture changes in the document

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Related Concepts

• Pipelines — How skills chain together
• Handoffs — Documents that pass between skills
• Modes & Registers — Adapting to different situations