Selective checkpoint marking within a single session

[akihirookuda95]

Problem or use case

As a RAG engineer, my typical development workflow involves multiple distinct phases within a single AI session:

1. Research Phase - Ask AI to perform web searches and discuss findings
2. Exploration Phase - Brainstorm various implementation approaches with AI
3. Implementation Trial Phase - Experimental code with multiple iterations
4. Validation Phase - Discuss validation results and document decisions

I want to record phases 1 and 4 (research and validation) to share with my team, but NOT phases 2 and 3 (exploration and trials), which are personal experimentation.

Current Problems

Problem 1: Cannot selectively record within a session

With the manual-commit strategy, the entire session is recorded as a single unit when I commit. This means I cannot record just the research discussions - all my exploratory brainstorming and trial-and-error implementations are also saved, which clutters the checkpoint and isn't useful for team sharing.

Problem 2: Research without file changes cannot create checkpoints

When I ask AI to perform web searches and discuss findings, often NO FILES ARE MODIFIED. This creates a fundamental issue:

git status
# nothing to commit, working tree clean

git commit -m "docs: Research on RAG evaluation metrics"
# ERROR: No files to commit
# Result: CANNOT CREATE CHECKPOINT even though this was valuable research

This forces me to either:

• Ask AI to write every research result to a Markdown file (adds overhead)
• Create dummy files just to enable commits (feels like a hack)
• Enable/disable Entire between phases (breaks the continuous flow and requires session restarts)

Real-world Example

I start a single Claude session and work through all four phases above. When I commit my work, the checkpoint includes ALL phases - the valuable research AND the messy trial-and-error. I cannot share just the research findings with my team without also exposing all my experimental work.

Desired behavior

I want to be able to:

1. **Work in a single continuous AI session** across multiple phases (research → exploration → implementation → validation)

2. **Manually mark specific moments** during the session that should be recorded as checkpoints, like:
   - "Research completed - mark this"
   - "Validation results - mark this"
   - Leave exploration and trials unmarked (not recorded)

3. **Create checkpoints even when no files have been modified** (for research-only discussions)

4. **When I commit, only the marked portions** of the session should be saved to the checkpoint

5. **Share only the valuable, marked portions** with my team while keeping exploratory work private

Proposed solution

Add an entire mark command that allows manual checkpoint marking within an active session.

Usage Example

claude  # Start session

# Phase 1: Research
> "Research Cohere Reranker optimization techniques"
# (AI performs web search, we discuss)

entire mark "research-completed" --description "Cohere Reranker research findings"
# ✅ Marks this point for recording, works even without file changes

# Phase 2: Exploration (no mark)
> "Let's explore different implementation approaches"
# (long discussion - NOT MARKED, won't be recorded)

# Phase 3: Trial implementation (no mark)
> "Try implementing approach A"
# (trial and error - NOT MARKED, won't be recorded)

# Phase 4: Validation
> "Validate the implementation with test data"
# (discuss results)

entire mark "validation-results" --description "Performance validation"
# ✅ Marks this point for recording

git commit -m "feat: Optimize Cohere Reranker parameters"
# Result: Only marked portions saved to checkpoint

Key Features

• Works while AI session is active (no need to exit/restart)
• Works regardless of file modifications (decoupled from git commit)
• Only marked portions saved to checkpoint
• Maintains conversational flow

Additional Commands

entire marks list              # List all marks in current session
entire marks remove <mark-id>  # Remove a mark before committing
entire marks preview           # View what will be recorded
entire status                  # Shows current session and marks

Implementation Considerations

• Marks should reference message ranges in the session transcript
• Checkpoint should contain only the marked conversation portions
• Backward compatible: unmarked sessions work as before
• Works with both manual-commit and auto-commit strategies

Alternatives or workarounds

I've tried these workarounds, but they're all unsatisfactory:

Alternative 1: Split into multiple sessions

Run separate Claude sessions for research and implementation:

claude --session research     # for research only
claude --session implement    # for implementation

Problems:

• Loses conversational continuity
• Research insights don't carry over naturally
• Context switching overhead
• Cannot maintain flow of thought

Alternative 2: Enable/disable toggling

Turn Entire on for research, off for implementation:

entire enable    # research
entire disable   # implementation

Problems:

• Requires stopping and restarting Claude sessions
• Fundamentally incompatible with single continuous session
• Breaks natural workflow

Alternative 3: Force file creation for research

Ask AI to always write research to Markdown files:

> "Research X and write findings to docs/research.md"

Problems:

• Adds overhead to every research task
• Creates unnecessary files in repository
• Sometimes I just want to discuss, not document

Alternative 4: Create dummy files

Add meaningless files just to enable commits

Problems:

• Pollutes repository
• Feels like a hack
• Not a real solution

Alternative 5: push_sessions=false

Set push_sessions to false in configuration

Problems:

• Everything still recorded locally (no selectivity)
• Cannot push specific checkpoints to team
• All-or-nothing when sharing