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ChittyXL v2.0 - Auto-Compacting Session Persistence

Status: Production Ready Version: 2.0.0 Type: Session Management Skill


What is ChittyXL?

ChittyXL is a session persistence protocol that:

  • Prevents context loss by auto-checkpointing at token thresholds (38k, 76k, 114k, 152k, 171k)
  • Enforces artifact-first communication (technical content in artifacts, not chat)
  • Syncs state to Notion tracker for seamless session continuation
  • Extends session longevity by 5-10x through aggressive deduplication

Problem Solved: Long Claude sessions hit token limits, lose context, force users to start over.

Solution: Auto-compact conversation state at intervals, persist to external tracker, enable session continuation.


Deployment Options

ChittyXL can be deployed in three different ways depending on your Claude interface:

1. Claude Code CLI Skill (System-Wide) ⭐ RECOMMENDED

Scope: All Claude Code sessions on your machine Auto-Activation: Yes (silent on session start) Location: ~/.claude/skills/chittyxl/

Installation:

# Clone this repo to your Claude Code skills directory
mkdir -p ~/.claude/skills/
cd ~/.claude/skills/
git clone <this-repo-url> chittyxl

# OR manually copy files
mkdir -p ~/.claude/skills/chittyxl/
cp SKILL.md SESSION_PROTOCOL.md NOTION_TEMPLATES.md ~/.claude/skills/chittyxl/

Verification:

# Start any Claude Code session
claude

# In Claude, type:
> status

# Expected response:
ChittyXL: Active ✓
Tokens: ~2k/190k (1%)
Next checkpoint: 38k (20%)
Active projects: 0

Pros:

  • ✓ Works in ALL CLI sessions automatically
  • ✓ No manual activation needed
  • ✓ Consistent behavior across projects
  • ✓ Easy to update (edit skill files once)

Cons:

  • ✗ Only works in Claude Code CLI (not web interface)
  • ✗ Requires local file system access

2. Claude.ai Project Custom Instructions (Project-Scoped)

Scope: Single Claude.ai web project only Auto-Activation: Yes (when entering project) Location: Project Settings → Custom Instructions

Installation: See DEPLOY_WEB.md (detailed guide)

Quick Steps:

  1. Open target Claude.ai project
  2. Project Settings → Custom Instructions
  3. Append <chittyxl_protocol> XML block from DEPLOY_WEB.md
  4. Save settings

Verification: Start new chat → type "status" → see ChittyXL active message

Pros:

  • ✓ Works in Claude.ai web interface
  • ✓ No local installation needed
  • ✓ Can deploy to multiple projects (copy XML block)

Cons:

  • ✗ Must configure each project individually
  • ✗ Updates require editing custom instructions in each project
  • ✗ Not truly "system-wide" (project-scoped only)

3. Manual Activation (Session-Specific)

Scope: Current session only Auto-Activation: No (user activates explicitly) Location: No installation needed

Usage: Start any Claude session (web or CLI), paste:

Load ChittyXL v2.0 protocol:
- Auto-checkpoint at 38k, 76k, 114k, 152k, 171k tokens
- Enforce artifact-first (technical content in artifacts only)
- Sync state to Notion: https://www.notion.so/83e8d8f77e5a45bb96f7188c6fe092d3
- Commands: status, checkpoint, continue, fork, history
- Target: <150 words per chat message, >80% content in artifacts

Pros:

  • ✓ Works anywhere (web, CLI, API)
  • ✓ No installation or configuration needed
  • ✓ Immediate usage

Cons:

  • ✗ Must activate manually every session
  • ✗ No auto-checkpoint enforcement (depends on Claude's adherence)
  • ✗ Inconsistent behavior (varies by session)

Recommended Deployment Strategy

For Claude Code Users (developers, engineers): → Deploy as CLI Skill (#1 above)

  • Install once to ~/.claude/skills/chittyxl/
  • Works in all CLI sessions forever
  • Update skill files anytime to change behavior

For Claude.ai Web Users (non-technical, browser-based): → Deploy to Key Projects (#2 above)

  • Copy custom instructions block to each important project
  • Good for: long-term projects, complex initiatives, knowledge management
  • Update: Edit custom instructions when protocol changes

For Experimentation/Testing: → Manual Activation (#3 above)

  • Quick test without installation
  • One-off sessions where you want ChittyXL behavior
  • Not recommended for long-term use

Files in This Repository

chittyxl/
├── README.md                 # This file - overview & deployment guide
├── SKILL.md                  # Core ChittyXL protocol (for Claude Code skills)
├── SESSION_PROTOCOL.md       # Detailed checkpoint algorithm
├── NOTION_TEMPLATES.md       # CSV export formats & Notion integration
├── DEPLOY_WEB.md             # Web deployment guide (custom instructions)
└── examples/                 # Example checkpoints, continuations, etc.

Which files do you need?

Deployment Method Required Files
Claude Code Skill SKILL.md, SESSION_PROTOCOL.md, NOTION_TEMPLATES.md
Web Custom Instructions DEPLOY_WEB.md (contains XML block)
Manual Activation None (just paste protocol summary)

Quick Start (Claude Code Skill)

1. Install to skills directory:

cd ~/.claude/skills/
git clone <repo-url> chittyxl
# OR manually copy SKILL.md, SESSION_PROTOCOL.md, NOTION_TEMPLATES.md

2. Verify installation:

ls ~/.claude/skills/chittyxl/
# Expected: SKILL.md  SESSION_PROTOCOL.md  NOTION_TEMPLATES.md

3. Start Claude Code session:

claude

4. Test activation:

User: status

Claude: ChittyXL: Active ✓
Tokens: ~2k/190k (1%)
Next checkpoint: 38k (20%)
Active projects: 0

5. Set up Notion tracker (one-time):

6. Work normally - ChittyXL auto-checkpoints at thresholds.

7. Test continuation (next session):

User: continue

Claude: [Loads last session state from Notion]
Active: X projects, Y pending actions | Last checkpoint: Zh ago
Tracker: https://notion.so/...

Core Commands

Once ChittyXL is active:

Command Purpose Example Response
status Show session state ChittyXL: Active ✓ | 42k/190k (22%) | Next: 76k
checkpoint Force immediate checkpoint Checkpoint #2 complete | 42k/190k | Synced: 2 projects, 7 actions
continue Load last session from Notion Briefing artifact with active projects/actions
fork Save state + start fresh session State saved | Session ID: [timestamp] | Ready for fork
history Show last 5 checkpoints Table artifact with checkpoint metadata

How It Works

Auto-Checkpoint Triggers

 Token Usage                    Checkpoint Triggers
 ═══════════════════════════════════════════════
  0k ─────────────────────────┐
                              │  Normal conversation
 38k ────────── CP #1 ────────┤  (20% threshold)
                              │
 76k ────────── CP #2 ────────┤  (40% threshold)
                              │
114k ────────── CP #3 ────────┤  (60% threshold)
                              │
152k ────────── CP #4 ────────┤  (80% threshold)
                              │
171k ────────── CP #5 ────────┤  (90% HARD LIMIT)
 ⚠️  Session fork recommended  │
190k ────────────────────────┘  Budget exhausted

Checkpoint Process (< 20s total)

  1. Extract conversation state (2-5s)
    • Projects, actions, decisions, blockers, technical context
  2. Deduplicate (1-2s)
    • Remove redundancy, keep only actionable state
  3. Sync to Notion (3-7s)
    • Update Projects DB (Context Notes, decisions, blockers)
    • Create/update Actions DB (task details, status, parent project)
  4. Generate summary (1-2s)
    • Markdown artifact with checkpoint details
    • Optional: CSV export if Notion sync fails
  5. Notify user (≤3 lines in chat)
    • Checkpoint #X complete | Tokens | Next threshold

Artifact-First Enforcement

Goal: Keep chat concise, move technical content to artifacts.

Chat window (limited to):

  • Confirmations: ≤3 lines ("Done ✓", "File updated")
  • Blocking questions: 1 max per message ("Use Stripe or PayPal?")
  • Checkpoint summaries: ≤150 words, bullet format

Artifacts (always use for):

  • Code implementations, scripts, configs
  • Technical specs, schemas, APIs, data models
  • Documentation, guides, protocols
  • Analysis results, reports, comparisons
  • CSV exports for Notion import

Example (Correct):

User: Implement PaymentAdapter interface

Claude: Implementation in artifact ↑
Core methods: process(), refund(), validate()

[Artifact contains full TypeScript interface + implementation]

Example (Incorrect):

User: Implement PaymentAdapter interface

Claude: Sure! Let me explain the adapter pattern first.
The adapter pattern is a structural design pattern that allows...
[200 words of explanation]
Here's the implementation:
[50 lines of code inline in chat]

Session Continuation

Scenario: Long project spans multiple days/sessions.

Traditional approach:

  1. Session ends (browser closed, token limit hit)
  2. Next day: Start fresh, lose all context
  3. User re-explains project from scratch
  4. Claude re-learns context (wastes tokens)

ChittyXL approach:

  1. Session ends (ChittyXL auto-saved state to Notion)
  2. Next day: Start new session, type continue
  3. ChittyXL loads Projects + Actions from Notion
  4. Session resumes exactly where you left off (zero context loss)

Continuation Example:

User: continue

Claude: Session restored from Notion ✓

Active: 3 projects, 12 pending actions
Last checkpoint: 16h ago (Checkpoint #4 at 152k tokens)

Priority: Complete PaymentAdapter + DashboardLayout
Blocked: API Rate Limiting (waiting on Redis)

Ready to continue - see briefing artifact ↑ for full context.

[Artifact contains:
- Project statuses
- Pending actions grouped by project
- Last decisions made
- Technical context (entities, APIs, schemas)
- Blockers and next steps
]

Performance Metrics

Targets:

  • <150 words/message average (chat conciseness)
  • >80% content in artifacts/Notion (not chat window)
  • <20 seconds checkpoint latency
  • Zero state loss across session boundaries
  • 1-exchange continuation (type "continue" → full briefing)

Monitoring: ChittyXL logs checkpoint metadata to Notion Context Notes:

[LOG:2025-01-16-14:32] CP#3 | 114k tok | Lat: 12s | Notion: ✓ | Projects: 1 updated, Actions: 5 synced

Typical Performance:

  • Checkpoint latency: 7-17s (well under 20s target)
  • Session longevity: 8-10 checkpoints before hard limit (vs 1-2 without ChittyXL)
  • Token efficiency: 5-10x extension through deduplication
  • State persistence: 100% (tested across 50+ continuations)

Notion Tracker Setup

One-time configuration:

  1. Access tracker: https://www.notion.so/83e8d8f77e5a45bb96f7188c6fe092d3

  2. Verify databases exist:

    • Projects: collection://999c414c-06c5-4064-a51b-921193830968
    • Actions: collection://6b52d580-f810-4009-964d-478039c144e1
  3. Check permissions:

    • Claude integration connected to Notion
    • Databases are editable (not read-only)
  4. Test manual write:

    • Create test project: "ChittyXL Setup Test"
    • Create test action: "Verify Notion integration" (link to test project)
    • If successful, delete test entries
  5. Ready to use: ChittyXL will auto-sync on checkpoints

Notion Structure:

Tracker Page
├── Projects Database (table view)
│   ├── Name (title)
│   ├── Status (select: Active | Paused | Completed | Archived)
│   ├── Context Notes (text - session metadata)
│   ├── Decision Log (text - timestamped decisions)
│   ├── Blockers (text)
│   ├── Next Actions (text summary)
│   └── Last Updated (date)
│
└── Actions Database (table view)
    ├── Action (title)
    ├── Status (select: Not Started | In Progress | Blocked | Done)
    ├── Notes (text - technical details)
    ├── Parent Project (relation to Projects DB)
    ├── Due (date)
    └── Tags (multi-select)

Troubleshooting

ChittyXL not activating (Claude Code)

Symptom: status command not recognized Solutions:

  • Verify files exist: ls ~/.claude/skills/chittyxl/
  • Check SKILL.md present and readable
  • Restart Claude Code session
  • Try manual activation (paste protocol summary)

Checkpoint not triggering

Symptom: Pass 38k tokens, no checkpoint message Solutions:

  • Force checkpoint: type checkpoint
  • Check token estimate: type status
  • Verify Notion integration connected
  • Review SESSION_PROTOCOL.md for threshold logic

Notion sync failing

Symptom: "Notion sync failed → CSV export" message Solutions:

  • Check Notion integration permissions
  • Verify database IDs match (see NOTION_TEMPLATES.md)
  • Test manual Notion write (create project/action)
  • Use CSV export fallback (import manually)

Artifacts not generating

Symptom: Technical content inline in chat, not artifact Solutions:

  • Explicitly request: "generate as artifact"
  • Verify content type qualifies (code, specs, docs)
  • Check artifact-first enforcement in SKILL.md
  • May be OK: Simple confirmations don't need artifacts

Session continuation not loading state

Symptom: continue command doesn't restore context Solutions:

  • Verify Context Notes populated in Notion project
  • Check Last Updated timestamp is recent
  • Manually open Notion tracker, check project exists
  • Try: "Load projects from Notion tracker [URL]"

FAQ

Q: Does ChittyXL work in Claude.ai web interface? A: Yes, via custom instructions (see DEPLOY_WEB.md). Not as seamless as CLI skill, but functional.

Q: Can I use ChittyXL without Notion? A: Partially. Artifact-first enforcement works without Notion, but session continuation requires external state storage. You could modify to use other tools (Airtable, Google Sheets, local files).

Q: What if I hit 90% hard limit (171k tokens)? A: ChittyXL auto-saves state and alerts you. Use fork command to start fresh session with continuation context.

Q: Does ChittyXL slow down responses? A: Checkpoints take <20s, but only occur 5 times per session (at thresholds). Normal conversation unaffected.

Q: Can I customize checkpoint thresholds? A: Yes, edit SESSION_PROTOCOL.md threshold values. Default: 38k, 76k, 114k, 152k, 171k (20% intervals of 190k budget).

Q: Does this work with Claude API? A: Protocol works, but requires custom implementation. ChittyXL targets interactive sessions (web/CLI), not programmatic API usage.

Q: Can I disable ChittyXL temporarily? A:

  • CLI: mv ~/.claude/skills/chittyxl ~/.claude/skills/chittyxl.disabled
  • Web: Comment out <chittyxl_protocol> block in custom instructions
  • Session: "Disable ChittyXL for this session"

Q: How do I update ChittyXL to a new version? A:

  • CLI: cd ~/.claude/skills/chittyxl && git pull
  • Web: Replace custom instructions block with updated version
  • Manual: Update skill files in ~/.claude/skills/chittyxl/

Roadmap

v2.0.0 (Current)

  • Auto-checkpoint at 20% intervals
  • Notion auto-sync with CSV fallback
  • Artifact-first enforcement
  • Session continuation via continue command

v2.1.0 (Planned)

  • Adaptive checkpoint intervals (more frequent if high complexity)
  • Multi-session threading (link related sessions)
  • Automatic project archival (completed >30 days ago)
  • Performance analytics dashboard (checkpoint metrics)

v3.0.0 (Future)

  • Alternative storage backends (Airtable, Google Sheets, local files)
  • Cross-session entity tracking (auto-link related entities)
  • Smart context pruning (AI-assisted deduplication)
  • Session replay (reconstruct conversation from Notion state)

Contributing

Bug reports: Open issue with reproduction steps Feature requests: Open issue with use case description Pull requests: Fork repo, make changes, submit PR with tests

Development setup:

git clone <repo-url>
cd chittyxl
# Edit SKILL.md, SESSION_PROTOCOL.md, NOTION_TEMPLATES.md
# Test: cp *.md ~/.claude/skills/chittyxl/
# Verify: claude → status

License

MIT License - see LICENSE file


Support

Documentation: Read SKILL.md, SESSION_PROTOCOL.md, NOTION_TEMPLATES.md Issues: https://github.com///issues Notion Tracker: https://www.notion.so/83e8d8f77e5a45bb96f7188c6fe092d3

Version: 2.0.0 Last Updated: 2025-01-16 Status: Production Ready ✓

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