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ChatCLI provides two powerful mechanisms for conversation history control: intelligent compaction to reduce context size without losing critical information, and rewind to restore the conversation to an earlier point.

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/compact — Context Compaction

The /compact command reduces conversation history size so it fits within the model’s context window, preserving the most important information.

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Usage Modes

Without arguments, runs the 3-level compaction pipeline:
/compact
The automatic pipeline follows this order:
  1. Level 1 — Trimming (near-lossless): strips <reasoning> tags, compacts XML, removes duplicates
  2. Level 2 — Structured summarization: extracts facts (files read, modified, commands executed, decisions) in bullet point format
  3. Level 3 — Emergency truncation: drops middle messages, keeping system prompt and recent messages

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How It Works

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Message Preservation

In both modes:
  • System messages are always fully preserved
  • Recent messages (4 in guided, 10 in automatic) are kept verbatim
  • Only the middle block is summarized or removed
  • Metadata indicates the message is a summary (IsSummary: true)

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Example Output

After compaction, a summary message replaces the middle messages: 
[GUIDED COMPACT — covering 42 earlier messages | instruction: "preserve auth architecture"]

## Files Read
- pkg/auth/handler.go (120 lines) - HTTP handlers for authentication
- pkg/auth/middleware.go (85 lines) - JWT validation middleware

## Files Modified
- pkg/auth/handler.go:45-60 - Added refresh token endpoint

## Key Decisions
- JWT tokens expire in 15 minutes with refresh token rotation
- Middleware validates at gateway level, not per-service

## Errors & Resolutions
- "token expired" panic in middleware → added nil check on claims

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/rewind — Go Back in Time

/rewind lets you restore the conversation to an earlier point, undoing unwanted messages and responses.

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How It Works

ChatCLI automatically saves checkpoints of the conversation before each LLM call. You can revert to any of those points. 
/rewind
This displays an interactive menu: 
  REWIND — Select a checkpoint to restore
  ─────────────────────────────────────────
  [1]  14:32:05  28 msgs  implement the refresh token endpoint
  [2]  14:28:12  24 msgs  fix the JWT middleware bug
  [3]  14:25:01  20 msgs  analyze the authentication module
  [4]  14:20:33  16 msgs  (start)

  Select [1-4] or (q)uit:
Select the checkpoint number to restore. The history is reverted to the exact state at that point, including all messages and context.

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Keyboard Shortcut: Esc+Esc

Press Esc twice quickly (less than 500ms between presses) to open the rewind menu directly from the prompt, without typing /rewind.

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Limits

  • A maximum of 20 checkpoints are kept (oldest ones are discarded)
  • Checkpoints exist only in the current session (not persisted to disk)
  • When rewinding, checkpoints after the restored point are removed

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Unified History

ChatCLI uses a single history array shared across all modes (chat, agent, coder). This means:
  • Switching between /agent, /coder, and chat preserves all context
  • The AI doesn’t “forget” what was done in another mode
  • /compact and /rewind operate on the complete history, regardless of mode
Sessions saved with older ChatCLI versions that used separate per-mode histories are automatically converted when loaded — histories are merged in chronological order.

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When to Use

/compact (automatic)

When ChatCLI warns that the context is large, or when you notice degraded responses.

/compact <instruction>

When you know exactly which information is critical and must not be lost during compaction.

/rewind

When the AI took a wrong path, generated incorrect code, or you want to try a different approach.

Esc+Esc

Quick shortcut for rewind without leaving your typing flow.

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Next Steps

Session Management

Save and reuse conversations across projects.

Bootstrap and Memory

Customize the AI and maintain long-term context across sessions.