feat: auto-summarize checkpoints at commit time

CLAUDE.md

@@ -121,6 +121,41 @@ return fmt.Errorf("unknown strategy: %s", name)
 - `root.go` - Sets `SilenceErrors: true` on root command
 - `main.go` - Checks for `SilentError` before printing
 
+### Settings
+
+All settings access should go through the `settings` package (`cmd/entire/cli/settings/`).
+
+**Why a separate package:**
+The `settings` package exists to avoid import cycles. The `cli` package imports `strategy`, so `strategy` cannot import `cli`. The `settings` package provides shared settings loading that both can use.
+
+**Usage:**
+```go
+import "entire.io/cli/cmd/entire/cli/settings"
+
+// Load full settings object
+s, err := settings.Load()
+if err != nil {
+    // handle error
+}
+if s.Enabled {
+    // ...
+}
+
+// Or use convenience functions
+if settings.IsSummarizeEnabled() {
+    // ...
+}
+```
+
+**Do NOT:**
+- Read `.entire/settings.json` or `.entire/settings.local.json` directly with `os.ReadFile`
+- Duplicate settings parsing logic in other packages
+- Create new settings helpers without adding them to the `settings` package
+
+**Key files:**
+- `settings/settings.go` - `EntireSettings` struct, `Load()`, and helper methods
+- `config.go` - Higher-level config functions that use settings (for `cli` package consumers)
+
 ### Logging vs User Output
 
 - **Internal/debug logging**: Use `logging.Debug/Info/Warn/Error(ctx, msg, attrs...)` from `cmd/entire/cli/logging/`. Writes to `.entire/logs/`.

README.md

@@ -161,13 +161,34 @@ Personal overrides, gitignored by default:
 
 ### Configuration Options
 
-| Option                           | Values                           | Description                                    |
-| -------------------------------- | -------------------------------- | ---------------------------------------------- |
-| `strategy`                       | `manual-commit`, `auto-commit`   | Session capture strategy                       |
-| `enabled`                        | `true`, `false`                  | Enable/disable Entire                          |
-| `agent`                          | `claude-code`, `gemini`, etc.    | AI agent to integrate with                     |
-| `log_level`                      | `debug`, `info`, `warn`, `error` | Logging verbosity                              |
-| `strategy_options.push_sessions` | `true`, `false`                  | Auto-push `entire/sessions` branch on git push |
+| Option                                 | Values                           | Description                                    |
+| -------------------------------------- | -------------------------------- | ---------------------------------------------- |
+| `strategy`                             | `manual-commit`, `auto-commit`   | Session capture strategy                       |
+| `enabled`                              | `true`, `false`                  | Enable/disable Entire                          |
+| `agent`                                | `claude-code`, `gemini`, etc.    | AI agent to integrate with                     |
+| `log_level`                            | `debug`, `info`, `warn`, `error` | Logging verbosity                              |
+| `strategy_options.push_sessions`       | `true`, `false`                  | Auto-push `entire/sessions` branch on git push |
+| `strategy_options.summarize.enabled`   | `true`, `false`                  | Auto-generate AI summaries at commit time      |
+
+### Auto-Summarization
+
+When enabled, Entire automatically generates AI summaries for checkpoints at commit time. Summaries capture intent, outcome, learnings, friction points, and open items from the session.
+
+```json
+{
+  "strategy_options": {
+    "summarize": {
+      "enabled": true
+    }
+  }
+}
+```
+
+**Requirements:**
+- Claude CLI must be installed and authenticated (`claude` command available in PATH)
+- Summary generation is non-blocking: failures are logged but don't prevent commits
+
+**Note:** Currently uses Claude CLI for summary generation. Other AI backends may be supported in future versions.
 
 ### Settings Priority
 

cmd/entire/cli/checkpoint/checkpoint.go

@@ -254,6 +254,14 @@ type WriteCommittedOptions struct {
 	// InitialAttribution is line-level attribution calculated at commit time
 	// comparing checkpoint tree (agent work) to committed tree (may include human edits)
 	InitialAttribution *InitialAttribution
+
+	// Summary is an optional AI-generated summary for this checkpoint.
+	// This field may be nil when:
+	//   - summarization is disabled in settings
+	//   - summary generation failed (non-blocking, logged as warning)
+	//   - the transcript was empty or too short to summarize
+	//   - the checkpoint predates the summarization feature
+	Summary *Summary
 }
 
 // ReadCommittedResult contains the result of reading a committed checkpoint.

cmd/entire/cli/checkpoint/committed.go

@@ -341,6 +341,7 @@ func (s *GitStore) writeMetadataJSON(opts WriteCommittedOptions, basePath string
 		TranscriptLinesAtStart:      opts.TranscriptLinesAtStart,
 		TokenUsage:                  opts.TokenUsage,
 		InitialAttribution:          opts.InitialAttribution,
+		Summary:                     opts.Summary,
 	}
 
 	// Merge with existing metadata if present (multi-session checkpoint)

cmd/entire/cli/explain.go

@@ -16,7 +16,7 @@ import (
 	"entire.io/cli/cmd/entire/cli/checkpoint/id"
 	"entire.io/cli/cmd/entire/cli/logging"
 	"entire.io/cli/cmd/entire/cli/strategy"
-	"entire.io/cli/cmd/entire/cli/summarise"
+	"entire.io/cli/cmd/entire/cli/summarize"
 	"entire.io/cli/cmd/entire/cli/trailers"
 	"entire.io/cli/cmd/entire/cli/transcript"
 
@@ -285,7 +285,7 @@ func generateCheckpointSummary(w, _ io.Writer, store *checkpoint.GitStore, check
 
 	// Check if transcript exists
 	if len(result.Transcript) == 0 {
-		return fmt.Errorf("checkpoint %s has no transcript to summarise", checkpointID)
+		return fmt.Errorf("checkpoint %s has no transcript to summarize", checkpointID)
 	}
 
 	// Scope the transcript to only this checkpoint's portion
@@ -294,26 +294,11 @@ func generateCheckpointSummary(w, _ io.Writer, store *checkpoint.GitStore, check
 		return fmt.Errorf("checkpoint %s has no transcript content for this checkpoint (scoped)", checkpointID)
 	}
 
-	// Build condensed transcript for summarisation from the scoped portion
-	condensed, err := summarise.BuildCondensedTranscriptFromBytes(scopedTranscript)
-	if err != nil {
-		return fmt.Errorf("failed to parse transcript: %w", err)
-	}
-	if len(condensed) == 0 {
-		return fmt.Errorf("checkpoint %s transcript has no content to summarise", checkpointID)
-	}
-
-	input := summarise.Input{
-		Transcript:   condensed,
-		FilesTouched: result.Metadata.FilesTouched,
-	}
-
-	// Generate summary using Claude CLI
+	// Generate summary using shared helper
 	ctx := context.Background()
 	logging.Info(ctx, "generating checkpoint summary")
 
-	var generator summarise.Generator = &summarise.ClaudeGenerator{}
-	summary, err := generator.Generate(ctx, input)
+	summary, err := summarize.GenerateFromTranscript(ctx, scopedTranscript, result.Metadata.FilesTouched, nil)
 	if err != nil {
 		return fmt.Errorf("failed to generate summary: %w", err)
 	}
@@ -502,14 +487,14 @@ func extractPromptsFromTranscript(transcriptBytes []byte) []string {
 		return nil
 	}
 
-	condensed, err := summarise.BuildCondensedTranscriptFromBytes(transcriptBytes)
+	condensed, err := summarize.BuildCondensedTranscriptFromBytes(transcriptBytes)
 	if err != nil {
 		return nil
 	}
 
 	var prompts []string
 	for _, entry := range condensed {
-		if entry.Type == summarise.EntryTypeUser && entry.Content != "" {
+		if entry.Type == summarize.EntryTypeUser && entry.Content != "" {
 			prompts = append(prompts, entry.Content)
 		}
 	}
@@ -632,16 +617,16 @@ func formatTranscriptBytes(transcriptBytes []byte, fallback string) string {
 		return "  (none)\n"
 	}
 
-	condensed, err := summarise.BuildCondensedTranscriptFromBytes(transcriptBytes)
+	condensed, err := summarize.BuildCondensedTranscriptFromBytes(transcriptBytes)
 	if err != nil || len(condensed) == 0 {
 		if fallback != "" {
 			return fallback + "\n"
 		}
 		return "  (failed to parse transcript)\n"
 	}
 
-	input := summarise.Input{Transcript: condensed}
-	return summarise.FormatCondensedTranscript(input)
+	input := summarize.Input{Transcript: condensed}
+	return summarize.FormatCondensedTranscript(input)
 }
 
 // formatSummaryDetails formats the detailed sections of an AI summary.