feat: auto-summarize checkpoints at commit time

[khaong]

Summary

• Add automatic AI summary generation for checkpoints at commit time (manual-commit strategy only)
• Summary generation is opt-in via strategy_options.summarize.enabled configuration
• Uses checkpoint-scoped transcript (not entire session) for more focused summaries
• Non-blocking: failures are logged but don't prevent commits

Changes

Configuration (config.go)

• Add SummarizeOptions struct and GetSummarizeOptions() helper
• Reads from nested strategy_options.summarize.enabled in settings

Shared Helper (summarize/summarize.go)

• Add GenerateFromTranscript() function as shared helper
• Used by both explain --generate and auto-summarize at commit time
• Reduces code duplication between explain.go and manual_commit_condensation.go

Checkpoint Package

• Add Summary field to WriteCommittedOptions to allow strategies to pass pre-generated summaries

Strategy Integration (manual_commit_condensation.go)

• Add summary generation to CondenseSession() when enabled
• Scopes transcript using TranscriptLinesAtStart metadata
• Logs success/failure without blocking checkpoint creation

Documentation

• Add strategy_options.summarize.enabled to README configuration table
• Add "Auto-Summarization" section with configuration example and requirements

Breaking Change

The settings key has been renamed from strategy_options.summarise to strategy_options.summarize (US English spelling). Update any existing configuration files accordingly.

Test plan

• Unit tests for GetSummarizeOptions() with various config shapes
• Unit tests for GenerateFromTranscript() with mock generator
• All existing tests pass
• Manual test: enable summarize, make changes, commit, verify summary in metadata

Linear

Closes ENT-96

🤖 Generated with Claude Code

---

Note

Medium Risk
Adds an opt-in commit-time flow that shells out to the Claude CLI and persists new summary data into checkpoint metadata; failures are non-blocking but touch strategy condensation and metadata formats. Also renames the config key/package from summarise to summarize, which can break existing settings until updated.

Overview
Adds opt-in auto-summarization for manual-commit checkpoints: during CondenseSession, the strategy now scopes the transcript to the checkpoint portion and (when strategy_options.summarize.enabled is true) generates an AI summary and persists it into committed checkpoint metadata; generation is non-blocking and only logs warnings on failure.

Extends checkpoint metadata to carry summaries by adding Summary to WriteCommittedOptions and writing it into metadata.json, and refactors entire explain --generate to use the new shared summarize.GenerateFromTranscript helper.

Renames/cleans up summarization plumbing: the summarise package/spelling is renamed to summarize, transcript condensing is improved (filtering verbose skill injections and minimizing details for noisy tools like Skill/Read/WebFetch), and docs are updated to document strategy_options.summarize.enabled and the new settings package access pattern.

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[Copilot]

Pull request overview

This pull request adds automatic AI summary generation for checkpoints at commit time in the manual-commit strategy. The feature is opt-in via configuration and non-blocking (failures don't prevent commits).

Changes:

• Adds a shared GenerateFromTranscript() helper function for summary generation, refactoring common logic from the explain command
• Integrates auto-summarisation into the manual-commit strategy's checkpoint condensation flow with configuration-based enablement
• Extends checkpoint metadata to include optional AI-generated summaries

Reviewed changes

Copilot reviewed 9 out of 9 changed files in this pull request and generated 2 comments.

Show a summary per file

File	Description
cmd/entire/cli/summarise/summarise.go	Adds shared GenerateFromTranscript() function to reduce duplication between explain and auto-summarise features
cmd/entire/cli/summarise/summarise_test.go	Adds comprehensive unit tests for the new helper function with mock generators
cmd/entire/cli/strategy/manual_commit_condensation.go	Integrates summary generation into checkpoint condensation with scoped transcripts; adds configuration reading logic
cmd/entire/cli/explain.go	Refactors to use the new shared GenerateFromTranscript() helper instead of duplicated logic
cmd/entire/cli/config.go	Adds SummariseOptions struct and GetSummariseOptions() helper for reading summarise configuration
cmd/entire/cli/config_test.go	Adds tests for various configuration scenarios of the summarise feature
cmd/entire/cli/checkpoint/checkpoint.go	Adds Summary field to WriteCommittedOptions to allow strategies to pass pre-generated summaries
cmd/entire/cli/checkpoint/committed.go	Includes summary in checkpoint metadata serialization
README.md	Documents the new auto-summarisation feature with configuration examples and requirements

Comments suppressed due to low confidence (1)

cmd/entire/cli/checkpoint/committed.go:386

• When merging multi-session checkpoints, the Summary from the new session overwrites any existing summary without preserving the previous one. This is different from how InitialAttribution is handled (lines 383-386), where the existing attribution is preserved.

Consider whether the Summary should:

1. Be preserved from the first session (like InitialAttribution)
2. Be replaced with the latest session's summary (current behavior)
3. Somehow combine/merge summaries from both sessions

The current behavior means only the most recent session's summary will be retained in multi-session checkpoints. If this is intentional, consider adding a comment explaining the design choice.

		Summary:                     opts.Summary,
	}

	// Merge with existing metadata if present (multi-session checkpoint)
	if existingMetadata != nil {
		// Get existing session count (default to 1 for backwards compat)
		existingCount := existingMetadata.SessionCount
		if existingCount == 0 {
			existingCount = 1
		}
		metadata.SessionCount = existingCount + 1

		// Merge session IDs
		existingIDs := existingMetadata.SessionIDs
		if len(existingIDs) == 0 {
			// Backwards compat: old metadata only had SessionID
			existingIDs = []string{existingMetadata.SessionID}
		}
		metadata.SessionIDs = append(metadata.SessionIDs[:0], existingIDs...)
		metadata.SessionIDs = append(metadata.SessionIDs, opts.SessionID)

		// Merge agents (deduplicated, preserving order)
		existingAgents := existingMetadata.Agents
		if len(existingAgents) == 0 && existingMetadata.Agent != "" {
			// Backwards compat: old metadata only had Agent
			existingAgents = []agent.AgentType{existingMetadata.Agent}
		}
		metadata.Agents = mergeAgents(existingAgents, opts.Agent)
		// Keep Agent as the first agent for backwards compat
		if len(metadata.Agents) > 0 {
			metadata.Agent = metadata.Agents[0]
		}

		// Merge files touched (deduplicated)
		metadata.FilesTouched = mergeFilesTouched(existingMetadata.FilesTouched, opts.FilesTouched)

		// Sum checkpoint counts
		metadata.CheckpointsCount = existingMetadata.CheckpointsCount + opts.CheckpointsCount

		// Keep existing attribution - we calculated this for the first session based on all commits in the shadow branch already
		if existingMetadata.InitialAttribution != nil {
			metadata.InitialAttribution = existingMetadata.InitialAttribution
		}

[Copilot]

Pull request overview

Copilot reviewed 8 out of 8 changed files in this pull request and generated 4 comments.

[cursor]

Cursor Bugbot has reviewed your changes and found 1 potential issue.

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