Use the session id stored in metadata to generate a summary of the claude session's conversation and post it to the github/linear issue (so only PR/issue mode) when il finish is run

[acreeger]

This behavior should be configurable per loom type. The summary should be focused on relevant insights/learnings/mistakes that claude makes in order to enable claude to learn from past mistakes (eventually this could be used in a RAG or other kind of search by iloom or other agents. The implementation should use a prompt template similar to issue-prompt.txt or others, and injected into the headless claude invokation that generates the summary.

[acreeger]

Enhancement Analysis

Questions for Reporter

Question	Answer
Should the summary be posted as a comment on the issue/PR, or should it be stored elsewhere (e.g., a dedicated file in the repo)?	Assumption: Posted as a comment to the issue/PR
What should happen if summary generation fails (e.g., Claude API issues, session not found)? Should il finish continue or abort?	Assumption: il finish should continue with a warning, not abort
Should there be a CLI flag to skip summary generation (e.g., --no-summary)?	Assumption: Yes, add --no-summary flag
What metadata beyond "insights/learnings/mistakes" should be captured (e.g., duration, commands run, files changed)?	Assumption: Focus on insights/learnings/mistakes as stated
Should summaries be appended to existing comments or always create new comments?	Assumption: Create new comment for each summary
Is there a maximum length for the generated summary to avoid overwhelming the issue thread?	Assumption: No enforced limit, let Claude generate natural summary

Problem Summary
When developers finish working on an issue using il finish, there is no automated capture of insights, learnings, or mistakes from the Claude Code session, losing valuable context that could help Claude improve future work.

User Impact
Developers and AI agents lose valuable learning opportunities from completed sessions. Without automated summaries, insights about what worked, what didn't, and why decisions were made are lost, preventing future Claude sessions from learning from past mistakes.

Enhancement Goal
Automatically generate and post a summary of the Claude Code session to the GitHub/Linear issue when il finish is run (only for PR/issue loom types). The summary should focus on relevant insights, learnings, and mistakes to enable future learning and potential RAG/search integration. This behavior should be configurable per loom type.

Next Steps

• Reporter to confirm assumptions in the questions table above
• Technical analysis to identify integration points with session metadata and Claude headless invocation
• Implementation planning and execution

---

📋 Complete Context & Details (click to expand)

Enhancement Context

The enhancement builds on existing infrastructure:

• Session IDs are already stored in metadata (reference: issue il spin should use deterministic session ID for Claude Code resume support #305)
• The system already uses prompt templates like issue-prompt.txt
• Claude headless invocation is already used in the codebase
• The il finish command is the integration point

Configuration Requirements

• Behavior must be configurable per loom type (PR mode, issue mode, branch mode, etc.)
• Only PR/issue loom types should trigger summary generation
• Configuration should allow enabling/disabling this feature

Summary Generation Requirements

• Use session ID from metadata to retrieve conversation history
• Use a prompt template (similar to issue-prompt.txt pattern)
• Inject template into headless Claude invocation
• Focus summary on:
  • Insights gained during the session
  • Learnings about the codebase or problem
  • Mistakes made by Claude and how they were resolved

Future Use Case

• Summaries will eventually be used for RAG (Retrieval-Augmented Generation)
• May be searchable by iloom or other agents
• Should be structured to facilitate future indexing/retrieval

Technical Integration Points

• Session metadata storage (already implemented)
• il finish command workflow
• GitHub/Linear API for posting comments
• Claude headless invocation system
• Prompt template system

[acreeger]

Complexity Assessment

Classification: COMPLEX

Metrics:

• Estimated files affected: 6
• Estimated lines of code: 250-350
• Breaking changes: No
• Database migrations: No
• Cross-cutting changes: Yes (configuration propagation through layers)
• File architecture quality: Poor (finish.ts is 1,140 lines with multiple concerns)
• Overall risk level: Medium

Reasoning:

Although the initial scope appears simple (create service, modify finish command, add configuration), this is a COMPLEX issue due to TWO critical factors:

1. Large, Complex File Architecture: The finish.ts command is 1,140 lines with 13+ methods handling multiple concerns (issue workflow, PR workflow, GitHub PR workflow, cleanup, post-merge). Inserting session summary generation into this file requires understanding the complete workflow context and ensuring the summary is generated at the correct point (after merge succeeds but before cleanup).

2. Cross-Cutting Configuration Changes: The requirement to make this "configurable per loom type" (PR vs Issue vs Branch) requires coordinating configuration changes across multiple layers: SettingsManager (define schema and defaults), WorkflowPermissionSchema (add field), finish command (read and check configuration). This creates hidden complexity because the configuration flows through multiple architectural boundaries.

Technical Complexity Breakdown:

• Understanding finish.ts workflow structure to find correct insertion point (high cognitive load)
• Creating SessionSummaryService that integrates with ClaudeService and GitHub/Linear commenting (moderate)
• Adding configuration schema to SettingsManager with per-loom-type support (moderate)
• Creating and integrating session summary prompt template (low)
• Tests to cover multiple code paths in finish.ts (moderate)

[acreeger]

Analysis Phase

• Review existing codebase architecture (finish command, session metadata, Claude service)
• Research Claude session resume/conversation retrieval capabilities
• Map cross-cutting configuration flow for per-loom-type settings
• Identify integration points and affected files
• Document findings with complete technical reference

---

Executive Summary

This feature adds automatic session summary generation when il finish runs for issue/PR looms. The system will use the stored session ID from loom metadata to retrieve Claude Code conversation history from ~/.claude/projects/, generate an insights-focused summary via headless Claude invocation, and post it as a comment to the GitHub/Linear issue. The behavior should be configurable per loom type (issue/pr/regular) via the existing workflows settings structure.

Questions and Key Decisions

Question	Answer
Where is Claude Code conversation history stored?	~/.claude/projects/ organized by project paths, indexed in ~/.claude/history.jsonl
How do we retrieve conversation by session ID?	Read JSONL files from ~/.claude/projects/{project-path}/ and filter by session ID stored in loom metadata
Should summary generation be blocking or async?	Non-blocking with warning on failure (per existing comment assumption)
Which loom types should support summaries?	Only issue and pr types (branch type has no issue to comment on)

HIGH/CRITICAL Risks

• Claude Code data retention: By default, Claude Code deletes conversation history after 30 days (~/.claude/settings.json). Sessions older than 30 days may have no conversation to summarize.

Impact Summary

• 1 new service file: SessionSummaryService.ts
• 1 new prompt template: session-summary-prompt.txt
• 3 files requiring modification: finish.ts, SettingsManager.ts, PromptTemplateManager.ts
• Key integration point: After merge succeeds but before cleanup in executeIssueWorkflow() and executeGitHubPRWorkflow()

---

Complete Technical Reference (click to expand for implementation details)

Problem Space Research

Problem Understanding

When developers finish working on an issue using il finish, valuable insights from the Claude Code session (learnings, mistakes, decisions) are lost. This feature captures and posts these insights to the issue for future reference and potential RAG/search integration.

Architectural Context

• Fits into the il finish workflow after merge succeeds but before cleanup
• Leverages existing infrastructure: session ID storage (MetadataManager), prompt templates (PromptTemplateManager), Claude headless invocation (ClaudeService/launchClaude), issue commenting (MCP providers)
• Configuration follows existing per-loom-type pattern via workflows.{issue|pr}.generateSummary

Edge Cases Identified

• Session ID not found in metadata (legacy looms): Skip with warning
• Conversation files deleted (30-day retention): Skip with warning
• Issue tracker API failure: Continue finish workflow, log warning
• Branch-type looms: No issue to comment on - skip entirely

Third-Party Research Findings

Claude Code Conversation Storage

Source: WebSearch, Context7
Key Findings:

• Conversations stored in ~/.claude/projects/ organized by project path
• Index file at ~/.claude/history.jsonl maps session IDs to conversation files
• Format: JSONL (JSON Lines) with one JSON object per line
• Default 30-day retention (configurable in ~/.claude/settings.json)
• --resume [session-id] CLI flag confirms session ID is the primary lookup key

Claude CLI Headless Invocation

Source: Codebase analysis (src/utils/claude.ts)
Key Findings:

• launchClaude(prompt, { headless: true }) returns stdout as string
• Supports --output-format stream-json for progress tracking
• Can pass conversation context via prompt (no native "read session" flag)

Codebase Research Findings

Session ID Storage

Entry Point: /src/lib/MetadataManager.ts:22
Data Structure:

interface MetadataFile {
  sessionId?: string // Claude Code session ID for resume support
  // ...other fields
}

Generated in: /src/lib/LoomManager.ts:283 via generateDeterministicSessionId(worktreePath)
Algorithm: UUID v5 from worktree path (/src/utils/claude.ts:13-43)

Finish Command Integration Points

Entry Point: /src/commands/finish.ts:187 - execute() method
Issue Workflow: /src/commands/finish.ts:558-667 - executeIssueWorkflow()

• Summary should be generated at line ~664 (after performFastForwardMerge, before performPostMergeCleanup)
  GitHub PR Workflow: /src/commands/finish.ts:762-819 - executeGitHubPRWorkflow()
• Summary should be generated at line ~814 (after PR created/updated, before cleanup prompt)

Per-Loom-Type Configuration Pattern

Schema Location: /src/lib/SettingsManager.ts:33-58

export const WorkflowPermissionSchema = z.object({
  permissionMode: z.enum([...]).optional(),
  noVerify: z.boolean().optional(),
  startIde: z.boolean().default(true),
  // NEW: generateSummary: z.boolean().default(true) for issue/pr, false for regular
})

Usage Pattern: /src/lib/ClaudeService.ts:45-50

const workflowConfig =
  type === 'issue'
    ? this.settings.workflows.issue
    : type === 'pr'
      ? this.settings.workflows.pr
      : this.settings.workflows.regular

Prompt Template System

Manager: /src/lib/PromptTemplateManager.ts
Template Location: /templates/prompts/ (copied to dist/prompts/ on build)
Template Types: 'issue' | 'pr' | 'regular' | 'init' - needs new 'session-summary' type
Variable Substitution: substituteVariables() method at line 97

Issue Comment Creation

MCP Interface: /src/mcp/types.ts:140 - createComment(input: CreateCommentInput)
GitHub Provider: /src/mcp/GitHubIssueManagementProvider.ts:208
Linear Provider: /src/mcp/LinearIssueManagementProvider.ts:114
Integration Note: The finish command doesn't currently have direct access to MCP providers. Options:

1. Add IssueManagementProvider to FinishCommand constructor
2. Use GitHub CLI (gh issue comment) directly like other parts of codebase
3. Create new IssueTracker method for commenting

Similar Patterns Found

• /src/commands/finish.ts:586-587 - Settings loading for skipVerify configuration
• /src/lib/ClaudeService.ts:68-169 - Headless Claude invocation with prompt
• /src/lib/LoomManager.ts:282-296 - Metadata reading during loom operations

Affected Files

New Files

• /src/lib/SessionSummaryService.ts - New service to read conversation, generate summary, post comment
• /templates/prompts/session-summary-prompt.txt - Prompt template for summary generation

Modified Files

• /src/lib/SettingsManager.ts:33-58 - Add generateSummary boolean to WorkflowPermissionSchema
• /src/lib/SettingsManager.ts:64-89 - Add to WorkflowPermissionSchemaNoDefaults
• /src/lib/PromptTemplateManager.ts:77 - Add 'session-summary' to template type union
• /src/lib/PromptTemplateManager.ts:33 - Add new template variables (SESSION_CONVERSATION, ISSUE_NUMBER, etc.)
• /src/commands/finish.ts:558-667 - Integrate summary generation into executeIssueWorkflow()
• /src/commands/finish.ts:762-819 - Integrate summary generation into executeGitHubPRWorkflow()
• /src/commands/finish.ts:56-97 - Constructor: add dependencies for summary generation

Architectural Flow Analysis

Data Flow: Session Summary Generation

Entry Point: FinishCommand.execute() at /src/commands/finish.ts:187

Flow Path:

1. /src/commands/finish.ts:558 - executeIssueWorkflow() starts
2. /src/commands/finish.ts:615 - Load settings to check workflows.issue.generateSummary
3. (NEW) Read loom metadata from MetadataManager.readMetadata(worktreePath) to get sessionId
4. (NEW) Call SessionSummaryService.generateAndPostSummary({sessionId, issueNumber, worktreePath})
5. /src/lib/SessionSummaryService.ts (NEW) - Reads ~/.claude/projects/{project-path}/ JSONL files
6. /src/lib/SessionSummaryService.ts (NEW) - Filters conversation by session ID
7. /src/lib/PromptTemplateManager.ts:77 - Load session-summary template
8. /src/utils/claude.ts:131 - launchClaude(prompt, { headless: true }) to generate summary
9. /src/mcp/GitHubIssueManagementProvider.ts:208 or GitHub CLI - Post comment to issue

Affected Interfaces (ALL must be updated):

• WorkflowPermissionSchema at /src/lib/SettingsManager.ts:33 - Add generateSummary field
• WorkflowPermissionSchemaNoDefaults at /src/lib/SettingsManager.ts:64 - Add generateSummary field
• PromptTemplateManager.loadTemplate() type union at /src/lib/PromptTemplateManager.ts:77 - Add 'session-summary'
• TemplateVariables at /src/lib/PromptTemplateManager.ts:7 - Add SESSION_CONVERSATION, BRANCH_NAME

Critical Implementation Note: This is a cross-cutting change. The configuration flows from SettingsManager through FinishCommand to SessionSummaryService.

Integration Points

FinishCommand Dependencies

Current constructor (/src/commands/finish.ts:56-97) accepts:

• issueTracker, gitWorktreeManager, validationRunner, commitManager, mergeManager
• identifierParser, resourceCleanup, buildRunner, settingsManager, loomManager

New dependencies needed:

• MetadataManager - Already accessible via loomManager.metadataManager (private, may need exposure)
• SessionSummaryService (NEW) - Or create lazily like resourceCleanup

Comment Posting Options

1. Use MCP Provider (cleanest): Add IssueManagementProvider dependency
2. Use gh CLI (simpler): Shell out to gh issue comment like other parts of codebase
3. Add to IssueTracker interface (most integrated): Add createComment() method

Recommendation: Option 2 (GitHub CLI) for initial implementation - matches existing patterns and avoids adding MCP server dependency to CLI.

Medium Severity Risks

• Large conversation files: Conversations can exceed 200K tokens. Summary prompt should truncate or summarize incrementally.
• Conversation file format changes: Claude Code is actively developed; JSONL schema may change between versions.

Related Context

• MetadataManager: Stores session ID per loom in ~/.config/iloom-ai/looms/{slugified-path}.json
• SettingsManager: Uses Zod schemas with defaults, supports deep merging from global/project/local/CLI sources
• PromptTemplateManager: Supports conditional sections {{#IF VAR}}...{{/IF VAR}} and variable substitution

[acreeger]

Implementation Plan for Issue #308

Summary

Add automatic Claude Code session summary generation when il finish runs for issue/PR looms. The system uses stored session IDs from loom metadata to retrieve conversation context, generates an insights-focused summary via headless Claude invocation, and posts it as a comment to the GitHub/Linear issue. This is configurable per loom type via workflows.{issue|pr}.generateSummary.

Questions and Key Decisions

Question	Answer	Rationale
How to retrieve Claude Code conversation context?	Pass session ID to Claude via prompt context, not by reading conversation files	Claude Code stores conversations in ~/.claude/projects/ but format is undocumented. Instead, use --resume flag semantics - the session ID provides context continuity. The summary agent can ask Claude to reflect on its conversation.
Where to integrate summary generation?	After successful merge, before cleanup in executeIssueWorkflow() and executeGitHubPRWorkflow()	Ensures summary captures complete work, avoids generating summaries for failed merges
How to post comments to issues?	Use IssueManagementProviderFactory to create appropriate provider (GitHub/Linear)	Consistent with existing codebase patterns, supports both providers automatically
What if summary generation fails?	Log warning, continue with finish workflow	Per analysis comment assumption - non-blocking to avoid disrupting critical merge operations

High-Level Execution Phases

1. Configuration Schema: Add generateSummary boolean to WorkflowPermissionSchema (default: true for issue/pr, false for regular)
2. Prompt Template: Create session-summary-prompt.txt template with variables for session context
3. SessionSummaryService: New service that generates summary via headless Claude and posts to issue
4. Finish Command Integration: Call summary generation after merge succeeds in both issue and PR workflows
5. Testing: Unit tests for service, integration tests for finish command flow

Quick Stats

• 0 files for deletion
• 4 files to modify (SettingsManager.ts, PromptTemplateManager.ts, finish.ts, and schema types)
• 2 new files to create (SessionSummaryService.ts, session-summary-prompt.txt)
• Dependencies: None (uses existing launchClaude, IssueManagementProviderFactory)
• Estimated complexity: Medium

---

Complete Implementation Guide (click to expand for step-by-step details)

Automated Test Cases to Create

Test File: /src/lib/SessionSummaryService.test.ts (NEW)

Purpose: Unit tests for summary generation service

Click to expand complete test structure (35 lines)

describe('SessionSummaryService', () => {
  describe('generateAndPostSummary', () => {
    it('should generate summary via headless Claude and post to issue')
    it('should skip and log warning when sessionId is null (legacy loom)')
    it('should skip and log warning when loom type is "branch"')
    it('should skip when generateSummary setting is false')
    it('should continue workflow on Claude invocation failure (non-blocking)')
    it('should continue workflow on comment posting failure (non-blocking)')
    it('should use correct issue management provider based on settings')
    it('should include session context in prompt template variables')
  })
  
  describe('shouldGenerateSummary', () => {
    it('should return true for issue type when generateSummary not configured (default)')
    it('should return true for pr type when generateSummary not configured (default)')
    it('should return false for branch type regardless of configuration')
    it('should respect explicit generateSummary: false setting')
    it('should respect explicit generateSummary: true setting')
  })
})

Test File: /src/commands/finish.test.ts (MODIFY)

Purpose: Add integration tests for summary generation in finish workflow

Click to expand test additions (20 lines)

describe('session summary generation', () => {
  it('should call SessionSummaryService after successful merge for issue workflow')
  it('should call SessionSummaryService after PR creation in github-pr workflow')
  it('should skip summary when generateSummary is false in settings')
  it('should continue cleanup even if summary generation fails')
  it('should not call summary generation for branch-type looms')
  it('should pass correct worktree path and metadata to summary service')
})

Files to Modify

1. /src/lib/SettingsManager.ts:33-58, 64-89

Change: Add generateSummary boolean field to both WorkflowPermissionSchema and WorkflowPermissionSchemaNoDefaults

// In WorkflowPermissionSchema (line ~46-47, after startTerminal)
generateSummary: z
  .boolean()
  .default(true)
  .describe('Generate and post Claude session summary when finishing this workflow type'),
  
// In WorkflowPermissionSchemaNoDefaults (line ~86-87, after startTerminal)
generateSummary: z
  .boolean()
  .optional()
  .describe('Generate and post Claude session summary when finishing this workflow type'),

2. /src/lib/PromptTemplateManager.ts:7-33, 77, 97-193

Change: Add 'session-summary' to template type union and new template variables

// In TemplateVariables interface (line ~7), add:
SESSION_CONTEXT?: string  // Session ID for Claude to reference its conversation
BRANCH_NAME?: string      // Branch being finished
LOOM_TYPE?: string        // 'issue' or 'pr'

// In loadTemplate method (line 77), update type union:
async loadTemplate(templateName: 'issue' | 'pr' | 'regular' | 'init' | 'session-summary'): Promise<string>

// In substituteVariables method (line ~97), add variable substitutions:
if (variables.SESSION_CONTEXT !== undefined) {
  result = result.replace(/SESSION_CONTEXT/g, variables.SESSION_CONTEXT)
}
if (variables.BRANCH_NAME !== undefined) {
  result = result.replace(/BRANCH_NAME/g, variables.BRANCH_NAME)
}
if (variables.LOOM_TYPE !== undefined) {
  result = result.replace(/LOOM_TYPE/g, variables.LOOM_TYPE)
}

3. /src/commands/finish.ts:1-30, 44-54, 558-667, 762-819

Change: Import SessionSummaryService, add to constructor, call after merge in both workflows

// Add import (line ~18)
import { SessionSummaryService } from '../lib/SessionSummaryService.js'

// Add private field (line ~54)
private sessionSummaryService?: SessionSummaryService

// In executeIssueWorkflow (line ~663, after runPostMergeBuild, before performPostMergeCleanup)
// Generate session summary (non-blocking)
await this.generateSessionSummaryIfConfigured(parsed, worktree)

// In executeGitHubPRWorkflow (line ~814, after PR created, before handlePRCleanupPrompt)
// Generate session summary (non-blocking)
await this.generateSessionSummaryIfConfigured(parsed, worktree)

// Add new private method
private async generateSessionSummaryIfConfigured(
  parsed: ParsedFinishInput,
  worktree: GitWorktree
): Promise<void> {
  // Skip for branch type (no issue to comment on)
  // Load settings to check generateSummary config
  // Initialize SessionSummaryService if needed
  // Call service.generateAndPostSummary with non-blocking try/catch
}

New Files to Create

/src/lib/SessionSummaryService.ts (NEW)

Purpose: Orchestrates session summary generation and posting

Click to expand complete structure (55 lines)

// Service that generates and posts Claude session summaries
// Dependencies: PromptTemplateManager, launchClaude, IssueManagementProviderFactory, MetadataManager, SettingsManager

export interface SessionSummaryInput {
  worktreePath: string
  issueNumber: string | number
  branchName: string
  loomType: 'issue' | 'pr' | 'branch'
}

export class SessionSummaryService {
  constructor(
    private templateManager: PromptTemplateManager,
    private settingsManager: SettingsManager,
    private metadataManager: MetadataManager
  ) {}

  async generateAndPostSummary(input: SessionSummaryInput): Promise<void> {
    // 1. Read metadata to get sessionId
    // 2. Return early if sessionId is null (legacy loom)
    // 3. Return early if loomType is 'branch'
    // 4. Load settings to check generateSummary config
    // 5. Load session-summary template
    // 6. Substitute variables (SESSION_CONTEXT, ISSUE_NUMBER, BRANCH_NAME, LOOM_TYPE)
    // 7. Call launchClaude with headless: true
    // 8. Create provider via IssueManagementProviderFactory
    // 9. Post summary as issue comment
    // All steps wrapped in try/catch - log warning on failure, don't throw
  }

  shouldGenerateSummary(
    loomType: 'issue' | 'pr' | 'branch',
    settings: IloomSettings
  ): boolean {
    // Return false for branch type
    // Check workflows.{issue|pr}.generateSummary setting
    // Default to true for issue/pr types
  }
}

/templates/prompts/session-summary-prompt.txt (NEW)

Purpose: Prompt template for generating session summaries

Click to expand complete template (40 lines)

You are generating a summary of a Claude Code development session.

## Session Context
- Session ID: SESSION_CONTEXT
- Issue/PR: #ISSUE_NUMBER
- Branch: BRANCH_NAME
- Loom Type: LOOM_TYPE

## Your Task

Reflect on the conversation from this development session and generate a concise summary focused on:

1. **Key Insights**: What important learnings emerged during implementation?
2. **Decisions Made**: What significant technical decisions were made and why?
3. **Challenges Encountered**: What obstacles were faced and how were they resolved?
4. **Mistakes and Corrections**: What mistakes were made and what was learned from them?

## Output Format

Generate a markdown comment suitable for posting to the issue. Structure it as:

```markdown
## Session Summary

### Key Insights
- [Insight 1]
- [Insight 2]

### Decisions Made
- [Decision and rationale]

### Challenges Resolved
- [Challenge and resolution]

### Lessons Learned
- [What could be done better next time]

Keep the summary concise (under 500 words). Focus on information that would help future developers or AI agents working on similar tasks.

</details>

## Detailed Execution Order

### Phase 1: Configuration Schema (SettingsManager)
1. Edit `/src/lib/SettingsManager.ts:46-47` - Add `generateSummary` to `WorkflowPermissionSchema` with default `true` -> Verify: TypeScript compiles
2. Edit `/src/lib/SettingsManager.ts:86-87` - Add `generateSummary` to `WorkflowPermissionSchemaNoDefaults` as optional -> Verify: TypeScript compiles

### Phase 2: Prompt Template System
1. Create `/templates/prompts/session-summary-prompt.txt` with template content -> Verify: File exists
2. Edit `/src/lib/PromptTemplateManager.ts:7-33` - Add new template variables interface fields -> Verify: TypeScript compiles
3. Edit `/src/lib/PromptTemplateManager.ts:77` - Add `'session-summary'` to type union -> Verify: TypeScript compiles
4. Edit `/src/lib/PromptTemplateManager.ts:97-193` - Add variable substitutions -> Verify: TypeScript compiles

### Phase 3: SessionSummaryService
1. Create `/src/lib/SessionSummaryService.ts` with service implementation -> Verify: TypeScript compiles
2. Create `/src/lib/SessionSummaryService.test.ts` with unit tests -> Verify: Tests pass

### Phase 4: Finish Command Integration
1. Edit `/src/commands/finish.ts:1-30` - Add import for SessionSummaryService -> Verify: TypeScript compiles
2. Edit `/src/commands/finish.ts:44-54` - Add private field for service -> Verify: TypeScript compiles
3. Edit `/src/commands/finish.ts:663` - Call summary generation in `executeIssueWorkflow()` -> Verify: TypeScript compiles
4. Edit `/src/commands/finish.ts:814` - Call summary generation in `executeGitHubPRWorkflow()` -> Verify: TypeScript compiles
5. Add `generateSessionSummaryIfConfigured()` private method -> Verify: TypeScript compiles
6. Update `/src/commands/finish.test.ts` - Add integration tests -> Verify: Tests pass

### Phase 5: Build and Verification
1. Run `pnpm build` -> Verify: Build succeeds
2. Run `pnpm test` -> Verify: All tests pass

**NOTE:** Follow TDD approach - write tests before implementation for each component.

## Dependencies and Configuration

None - uses existing infrastructure:
- `launchClaude` from `src/utils/claude.ts`
- `IssueManagementProviderFactory` from `src/mcp/IssueManagementProviderFactory.ts`
- `MetadataManager` from `src/lib/MetadataManager.ts`
- `PromptTemplateManager` from `src/lib/PromptTemplateManager.ts`

</details>

[acreeger]

Implementation Complete - Issue #308

Summary

Added automatic Claude Code session summary generation when il finish runs for issue/PR looms. The system uses stored session IDs from loom metadata, generates an insights-focused summary via headless Claude invocation, and posts it as a comment to the GitHub/Linear issue. The behavior is configurable per loom type via workflows.{issue|pr}.generateSummary.

Changes Made

• SettingsManager.ts: Added generateSummary boolean field to WorkflowPermissionSchema (default: true) and WorkflowPermissionSchemaNoDefaults
• PromptTemplateManager.ts: Added session-summary template type and new variables (SESSION_CONTEXT, BRANCH_NAME, LOOM_TYPE)
• SessionSummaryService.ts (NEW): Service that orchestrates summary generation via headless Claude and posting to issues
• session-summary-prompt.txt (NEW): Prompt template focused on insights, decisions, challenges, and lessons learned
• finish.ts: Integrated summary generation after merge/PR creation (non-blocking)

Validation Results

• Tests: 2787 passed (including 15 new SessionSummaryService tests)
• Typecheck: Passed
• Lint: Passed
• Build: Passed

---

Detailed Changes by File (click to expand)

Files Modified

/src/lib/SettingsManager.ts

Changes: Added generateSummary boolean field to both workflow permission schemas

• Line 58-61: Added to WorkflowPermissionSchema with default true
• Line 93-96: Added to WorkflowPermissionSchemaNoDefaults as optional

/src/lib/PromptTemplateManager.ts

Changes: Added session-summary template support

• Lines 33-36: Added SESSION_CONTEXT, BRANCH_NAME, LOOM_TYPE to TemplateVariables interface
• Line 81: Updated loadTemplate type union to include 'session-summary'
• Lines 196-207: Added variable substitutions for new template variables
• Line 327: Updated getPrompt type union

/src/commands/finish.ts

Changes: Integrated session summary generation into finish workflows

• Line 19: Added import for SessionSummaryService
• Line 56: Added private field sessionSummaryService
• Lines 667-670: Added call in executeIssueWorkflow() after build, before cleanup
• Lines 823-824: Added call in executeGitHubPRWorkflow() after PR creation
• Lines 1001-1030: Added generateSessionSummaryIfConfigured() method

Files Created

/src/lib/SessionSummaryService.ts (NEW)

Purpose: Orchestrates session summary generation and posting

• Reads session ID from loom metadata
• Loads and processes session-summary prompt template
• Invokes Claude headless with haiku model
• Posts summary to issue via IssueManagementProvider
• Non-blocking: catches errors and logs warnings

/src/lib/SessionSummaryService.test.ts (NEW)

Purpose: Unit tests for SessionSummaryService (15 tests)

• Tests happy path summary generation and posting
• Tests skip conditions (branch type, no session ID, disabled setting)
• Tests non-blocking error handling
• Tests provider selection based on settings

/templates/prompts/session-summary-prompt.txt (NEW)

Purpose: Prompt template for summary generation

• Focuses on key insights, decisions, challenges, and lessons learned
• Structured markdown output suitable for issue comments
• Variables: SESSION_CONTEXT, ISSUE_NUMBER, BRANCH_NAME, LOOM_TYPE

Test Coverage Added

• /src/lib/SessionSummaryService.test.ts: 15 tests covering all service methods and edge cases

Dependencies Added

None - uses existing infrastructure (launchClaude, IssueManagementProviderFactory, MetadataManager, PromptTemplateManager)

[acreeger]

Implementation Complete - test-summary CLI Command

Summary

Added a new CLI command test-summary that generates Claude session summaries for looms. The command takes a loom identifier (issue number, PR number, or branch name), generates a summary using the existing SessionSummaryService, and prints it to stdout. An optional --with-comment flag posts the summary as a comment to the issue/PR (silently skipped for branch-type looms).

Changes Made

• SessionSummaryService.ts: Added generateSummary() method to return summary text, postSummary() public method for posting summaries, and SessionSummaryResult interface
• test-summary.ts (NEW): Command implementation with identifier parsing for issues, PRs, and branches
• test-summary.test.ts (NEW): 9 tests covering all command functionality
• cli.ts: Registered test-summary command with --with-comment option
• commands/index.ts: Exported TestSummaryCommand

Validation Results

• Tests: 2796 passed (including 9 new TestSummaryCommand tests)
• Typecheck: Passed
• Lint: Passed
• Build: Passed

---

Detailed Changes by File (click to expand)

Files Modified

/src/lib/SessionSummaryService.ts

Changes: Added new methods for standalone summary generation and posting

• Added SessionSummaryResult interface with summary and sessionId fields
• Added generateSummary() method that generates summary without posting (throws on error)
• Added postSummary() public method for posting summaries to issues

/src/cli.ts

Changes: Registered test-summary command

• Added test-summary command with <identifier> argument and --with-comment option

/src/commands/index.ts

Changes: Added exports for TestSummaryCommand

Files Created

/src/commands/test-summary.ts (NEW)

Purpose: CLI command for testing session summary generation

• Parses loom identifiers (issue numbers, PR numbers via pr/123, branch names)
• Uses GitWorktreeManager to find worktrees
• Reads metadata to get loom type and issue numbers
• Calls SessionSummaryService to generate and optionally post summaries
• Prints summary to stdout for piping/redirection

/src/commands/test-summary.test.ts (NEW)

Purpose: Unit tests for TestSummaryCommand (9 tests)

• Tests issue, PR, and branch identifier handling
• Tests --with-comment flag behavior
• Tests silent skip for branch type looms with --with-comment
• Tests error cases (loom not found, no session ID, no metadata)

Test Coverage Added

• /src/commands/test-summary.test.ts: 9 tests covering all command functionality

Dependencies Added

None

[acreeger]

Implementation Complete - Summary Command Improvements

Summary

Updated the summary command with two improvements: auto-detection of current loom when no identifier is provided, and deterministic session ID generation when metadata lacks a sessionId. Also ensured the command is named summary (renamed from test-summary).

Changes Made

• cli.ts: Updated command from test-summary to summary, made identifier argument optional [identifier]
• summary.ts: Added autoDetectFromCurrentDirectory() method, updated execute() to use deterministic session ID generation when metadata has no sessionId
• summary.test.ts: Added 4 new test cases for auto-detection and deterministic session ID generation

Validation Results

• Tests: 2800 passed (including 13 summary command tests)
• Typecheck: Passed
• Lint: Passed
• Build: Passed

---

Detailed Changes by File (click to expand)

Files Modified

/src/cli.ts

Changes: Renamed command from test-summary to summary, made identifier optional

• Changed .argument('<identifier>', ...) to .argument('[identifier]', ...)
• Updated action signature to accept identifier: string | undefined
• Updated error message from "Test summary failed" to "Summary failed"
• Updated description to mention auto-detection

/src/commands/summary.ts

Changes: Added auto-detection and deterministic session ID generation

• Added imports for path, extractIssueNumber, generateDeterministicSessionId
• Made identifier optional in SummaryCommandInput interface
• Updated execute() to call autoDetectFromCurrentDirectory() when no identifier provided
• Added deterministic session ID generation using generateDeterministicSessionId(worktreePath) when metadata lacks sessionId
• Added autoDetectFromCurrentDirectory() method (100 lines) that:
  • Checks for PR pattern (_pr_N suffix) in current directory
  • Checks for issue pattern in current directory
  • Falls back to current branch detection
  • Uses same logic as FinishCommand for consistency

/src/commands/summary.test.ts

Changes: Updated tests and added new test cases

• Added mocks for ../utils/git.js and ../utils/claude.js
• Added getRepoInfo mock to GitWorktreeManager
• Reorganized tests into execute with identifier, auto-detection from current directory, and deterministic session ID generation describe blocks
• Added 4 new test cases:
  • should auto-detect loom when no identifier provided
  • should auto-detect PR loom from directory with _pr_N suffix
  • should fall back to branch detection when directory has no issue pattern
  • should generate deterministic session ID when metadata has no sessionId
  • should generate deterministic session ID when metadata sessionId is undefined
• Removed test that expected error when session ID is missing (now generates deterministically instead)

Test Coverage Added

• /src/commands/summary.test.ts: 13 tests covering all command functionality including new auto-detection and deterministic session ID features

Dependencies Added

None

[acreeger]

Implementation Complete - Issue #308

Summary

Fixed the il summary command failing with "No session ID found in loom metadata" by ensuring the deterministic session ID is passed to SessionSummaryService.generateSummary().

Changes Made

• src/lib/SessionSummaryService.ts: Added optional providedSessionId parameter to generateSummary() method
• src/commands/summary.ts: Updated to pass the deterministic session ID to generateSummary()
• src/commands/summary.test.ts: Updated test assertions to include the 5th sessionId argument

Validation Results

• Tests: 2800 passed / 2801 total (1 skipped)
• Typecheck: Passed
• Lint: Passed
• Build: Passed

---

Detailed Changes by File (click to expand)

Files Modified

src/lib/SessionSummaryService.ts

Changes: Added providedSessionId parameter to generateSummary() method so callers can pass a pre-generated session ID instead of relying on metadata

src/commands/summary.ts

Changes: Updated the call to generateSummary() to pass the deterministic session ID generated at line 69

src/commands/summary.test.ts

Changes: Updated test assertions to expect the 5th sessionId parameter in generateSummary() calls

Root Cause

The SummaryCommand was correctly generating a deterministic session ID at line 69 when metadata lacked one, but then called generateSummary() without passing it. The generateSummary() method would re-read metadata and throw the error because it didn't know about the fallback session ID.

[acreeger]

Implementation Phase - Adding --json flag to summary command

Working on adding --json flag to the il summary command following existing codebase patterns.

Tasks

• Add SummaryResult type to types/index.ts
• Update SummaryOptions interface in summary.ts to include json option
• Update SummaryCommand.execute() to return result object in JSON mode
• Update cli.ts to handle JSON mode (withLogger pattern, console.log JSON output)
• Add tests for JSON mode behavior
• Run validation (typecheck, lint, tests, build)

ETA: ~5 minutes

[acreeger]

Analysis Phase - Session Transcript Research

Investigating Claude Code session transcript files to improve summary generation when conversations are compacted.

• Explore ~/.claude/projects/ directory structure
• Analyze session transcript file format (JSONL schema)
• Investigate how to map worktree path to transcript file
• Document technical constraints (file sizes, privacy, token limits)
• Provide recommendations for implementation approach

---

Executive Summary

Claude Code stores complete session transcripts in ~/.claude/projects/{encoded-path}/ as JSONL files. Critically, when conversations are compacted, the compact summary is stored in the transcript with isCompactSummary: true flag. This means the full conversation history (including pre-compaction content via the stored summary) is available for session summary generation even after compaction.

Questions and Key Decisions

Question	Answer
Does compaction lose conversation history?	No - The compact summary is stored in the JSONL with isCompactSummary: true and contains ~11K chars of summarized pre-compaction content
How to find transcript for a worktree?	Convert path to directory name: /Users/adam/... becomes -Users-adam-..., then find JSONL file with matching sessionId
Can we read transcripts directly?	Yes - JSONL files are plaintext and accessible at ~/.claude/projects/

HIGH/CRITICAL Risks

• File size: Main session transcript is 3MB (693 lines). Need to extract/summarize rather than pass entire file.
• Format stability: Claude Code is actively developed; JSONL schema could change between versions.

Impact Summary

Two potential implementation approaches discovered:

1. Read transcript directly: Parse JSONL, extract compact summaries and key messages, pass to summary generation
2. Current approach improvement: The --resume <sessionId> already provides context; the issue may be prompt design, not data access

---

Complete Technical Reference (click to expand for implementation details)

Session Transcript File Format

Location

• Directory: ~/.claude/projects/{encoded-path}/
• Path encoding: Absolute path with / replaced by - and leading - (e.g., /Users/adam/Projects/foo becomes -Users-adam-Projects-foo)
• Session files: {sessionId}.jsonl - main conversation, agent-{shortId}.jsonl - sub-agent conversations

File Structure

Each line is a JSON object with one of these types:

• "type": "user" - User messages
• "type": "assistant" - Claude responses
• "type": "system" - System events (including compaction markers)
• "type": "file-history-snapshot" - File backup metadata
• "type": "queue-operation" - Internal queue operations

Key Fields (User/Assistant Messages)

{
  "parentUuid": "<uuid>",        // Links to parent message for conversation tree
  "sessionId": "<uuid>",         // Session identifier
  "type": "user|assistant",
  "message": {
    "role": "user|assistant",
    "content": "<text>" | [{ "type": "text|tool_use|tool_result", ... }]
  },
  "timestamp": "<ISO8601>",
  "uuid": "<uuid>",
  "version": "2.0.67",           // Claude Code version
  "gitBranch": "<branch>",
  "cwd": "<path>"
}

Compaction Handling

When a conversation is compacted, TWO entries are written:

1. Compact Boundary Marker:

{
  "type": "system",
  "subtype": "compact_boundary",
  "content": "Conversation compacted",
  "compactMetadata": {
    "trigger": "manual",
    "preTokens": 162930
  }
}

2. Compact Summary (THE PRESERVED HISTORY):

{
  "type": "user",
  "isCompactSummary": true,
  "isVisibleInTranscriptOnly": true,
  "message": {
    "role": "user",
    "content": "This session is being continued from a previous conversation that ran out of context. The conversation is summarized below:\nAnalysis:\n[...11K chars of summarized conversation...]"
  }
}

Key Finding: The compact summary contains a structured summary of EVERYTHING that happened before compaction, including:

• Chronological sequence of events
• Key decisions made
• Errors and fixes
• User messages summary
• Current work state

Index File

~/.claude/history.jsonl maps sessions to projects:

{"display":"<first user message>","project":"/path/to/project","sessionId":"<uuid>","timestamp":<epoch>}

Mapping Worktree to Transcript

Algorithm

1. Take worktree absolute path (e.g., /Users/adam/Documents/Projects/iloom-cli/feat-issue-308__claude-session-summary)
2. Replace all / with - to get directory name (-Users-adam-Documents-Projects-iloom-cli-feat-issue-308__claude-session-summary)
3. Look in ~/.claude/projects/{directory-name}/
4. Find JSONL file matching session ID from loom metadata

Session ID Sources

1. Loom metadata: ~/.config/iloom-ai/looms/{slug}.json contains sessionId
2. Deterministic generation: generateDeterministicSessionId(worktreePath) in /src/utils/claude.ts:13-43
3. History index: ~/.claude/history.jsonl maps sessions to projects

File Size Analysis

For issue #308 session:

• Main transcript: 2.2MB, 693 lines (221 user, 398 assistant messages)
• Agent transcripts: 100KB-1MB each
• Compact summary: ~11K chars when stored

Implementation Approaches

Approach 1: Direct Transcript Reading

Pros: Full access to all messages including pre-compaction content
Cons: Complex parsing, format may change, large files

Steps:

1. Map worktree path to Claude projects directory
2. Find JSONL file with matching session ID
3. Parse JSONL and extract:
   • Compact summaries (isCompactSummary: true)
   • Key user messages (filter by importance)
   • Error/fix patterns from tool results
4. Pass extracted content to summary prompt

Approach 2: Improve Current --resume Approach

Pros: Uses official Claude Code API, simpler
Cons: May still not capture all pre-compaction context

The current implementation passes --session-id <uuid> which should resume the session context. The issue may be:

• Prompt doesn't explicitly ask Claude to include pre-compaction context
• Model may not have access to the compact summary via API

Approach 3: Hybrid

Read transcript to extract compact summaries, then pass as context alongside --resume:

// Pseudocode
const compactSummaries = extractCompactSummaries(transcriptPath, sessionId)
const prompt = `
Previous conversation summaries:
${compactSummaries.join('\n\n')}

Now summarize THIS conversation including the above context...
`
await launchClaude(prompt, { sessionId, headless: true })

Affected Files

If implementing direct transcript reading:

• /src/lib/SessionSummaryService.ts:61-121 - Add transcript reading before Claude invocation
• /src/utils/claude.ts - Add new utility readSessionTranscript(sessionId, worktreePath)
• New: /src/utils/claude-transcript.ts - Transcript parsing utilities

Technical Constraints

1. Token limits: Compact summaries are ~11K chars. Multiple summaries could exceed context.
2. Privacy: Transcripts contain full conversation history including tool results with file contents.
3. File permissions: Transcripts are 0600 (owner read/write only).
4. Version compatibility: Schema includes version field (currently "2.0.67"). May need version checks.

Similar Patterns Found

• /src/lib/MetadataManager.ts - Reading JSONL-like config files
• /src/utils/claude.ts:101-125 - Parsing JSON stream output

[acreeger]

Implementation Plan for Issue #308 - Session Transcript Enhancement

Summary

Enhance session summary generation by reading Claude Code transcript files to extract compact summaries (pre-compaction context) and pass them as additional context to the summary generation prompt. This solves the problem where --resume <sessionId> only provides post-compaction context, losing valuable conversation history.

Questions and Key Decisions

Question	Answer	Rationale
How to find transcript files?	Map worktree path to Claude projects directory using path encoding	/Users/adam/Projects/foo becomes ~/.claude/projects/-Users-adam-Projects-foo/
What content to extract?	Compact summaries (isCompactSummary: true entries)	These contain ~11K chars each of structured conversation history
How to handle multiple compact summaries?	Concatenate all, newest first	Provides complete pre-compaction context chronologically
What if transcript not found?	Graceful degradation - use current behavior	Maintains backward compatibility
Token limits for context?	Limit to most recent 3 compact summaries (~33K chars)	Balances context with prompt size limits

High-Level Execution Phases

1. Transcript Reader Utility: Create src/utils/claude-transcript.ts with functions to read and parse transcript files
2. SessionSummaryService Enhancement: Add method to extract compact summaries and include in prompt context
3. Prompt Template Update: Add COMPACT_SUMMARIES variable to include extracted context
4. Testing: Add unit tests for transcript reader and updated service behavior

Quick Stats

• 0 files for deletion
• 2 files to modify (SessionSummaryService.ts, session-summary-prompt.txt)
• 1 new file to create (claude-transcript.ts)
• Dependencies: None (uses existing fs-extra, os, path)
• Estimated complexity: Medium

---

Complete Implementation Guide (click to expand for step-by-step details)

Automated Test Cases to Create

Test File: /src/utils/claude-transcript.test.ts (NEW)

Purpose: Unit tests for transcript reading utilities

Click to expand complete test structure (40 lines)

describe('claude-transcript', () => {
  describe('getClaudeProjectsDir', () => {
    it('should return ~/.claude/projects/ path')
    it('should encode worktree path correctly (/ -> -)')
  })

  describe('getTranscriptPath', () => {
    it('should return correct path for worktree and sessionId')
    it('should handle paths with special characters')
  })

  describe('extractCompactSummaries', () => {
    it('should extract all compact summaries from transcript')
    it('should return empty array when no compact summaries exist')
    it('should parse JSONL format correctly')
    it('should handle malformed JSON lines gracefully')
    it('should limit to most recent N summaries when specified')
    it('should return summaries in reverse chronological order')
  })

  describe('readSessionTranscript', () => {
    it('should return compact summaries for valid session')
    it('should return empty array when transcript file not found')
    it('should return empty array when session ID not in transcript')
    it('should handle permission errors gracefully')
  })
})

Test File: /src/lib/SessionSummaryService.test.ts (MODIFY)

Purpose: Add tests for transcript reading integration

// Add to existing describe block
it('should include compact summaries in prompt when transcript exists')
it('should work without compact summaries (short sessions)')
it('should handle transcript read errors gracefully')

New Files to Create

/src/utils/claude-transcript.ts (NEW)

Purpose: Read and parse Claude Code session transcript files

Click to expand complete structure (65 lines)

import { readFile } from 'fs/promises'
import { homedir } from 'os'
import { join } from 'path'
import { logger } from './logger.js'

/**
 * Entry in a Claude Code JSONL transcript file
 */
export interface TranscriptEntry {
  type: 'user' | 'assistant' | 'system' | 'file-history-snapshot'
  sessionId?: string
  message?: { role: string; content: string }
  isCompactSummary?: boolean
  subtype?: string  // 'compact_boundary' for compaction markers
  content?: string
  timestamp?: string
}

/**
 * Get the Claude projects directory for a worktree path
 * Encoding: /Users/adam/Projects/foo -> -Users-adam-Projects-foo
 */
export function getClaudeProjectsDirName(worktreePath: string): string {
  // Replace all '/' with '-' (including leading slash)
  return worktreePath.replace(/\//g, '-')
}

/**
 * Get the full path to Claude projects directory
 */
export function getClaudeProjectsPath(): string {
  return join(homedir(), '.claude', 'projects')
}

/**
 * Extract compact summaries from a session transcript
 * Returns empty array if file doesn't exist or no summaries found
 * 
 * @param worktreePath - Absolute path to worktree
 * @param sessionId - Session ID to find transcript for
 * @param maxSummaries - Maximum number of summaries to return (default 3)
 * @returns Array of compact summary content strings, newest first
 */
export async function extractCompactSummaries(
  worktreePath: string,
  sessionId: string,
  maxSummaries = 3
): Promise<string[]> {
  // 1. Build transcript file path
  // 2. Read file, return [] if not exists
  // 3. Parse JSONL, filter for isCompactSummary: true
  // 4. Extract message.content from each
  // 5. Return most recent N, newest first
}

/**
 * Read session transcript and extract relevant context for summary generation
 * Gracefully handles all error cases (file not found, parse errors, etc.)
 */
export async function readSessionContext(
  worktreePath: string,
  sessionId: string
): Promise<string | null> {
  // 1. Call extractCompactSummaries
  // 2. If empty, return null
  // 3. Join summaries with separator
  // 4. Return formatted context string
}

Files to Modify

1. /src/lib/SessionSummaryService.ts:61-96, 136-182

Change: Add transcript reading before Claude invocation and include in prompt context

// At line ~82, before loading template:
// Extract compact summaries from session transcript
const compactContext = await readSessionContext(input.worktreePath, sessionId)

// At line ~83-87, update template variables:
const prompt = await this.templateManager.getPrompt('session-summary', {
  ISSUE_NUMBER: String(input.issueNumber),
  BRANCH_NAME: input.branchName,
  LOOM_TYPE: input.loomType,
  COMPACT_SUMMARIES: compactContext ?? '',  // NEW: Add transcript context
})

Similarly update generateSummary() method at lines 136-182.

2. /src/lib/PromptTemplateManager.ts:33-37

Change: Add COMPACT_SUMMARIES to TemplateVariables interface

// Add after LOOM_TYPE (line ~36):
COMPACT_SUMMARIES?: string  // Extracted compact summaries from session transcript

3. /templates/prompts/session-summary-prompt.txt:1-61

Change: Update prompt to use compact summaries when available

Click to expand updated template (75 lines)

You are generating a summary of THIS conversation - the development session you just completed.

## Context
- Issue/PR: #ISSUE_NUMBER
- Branch: BRANCH_NAME
- Loom Type: LOOM_TYPE

{{#IF COMPACT_SUMMARIES}}
## Previous Conversation Context

The following summaries capture the earlier parts of this session that were compacted to save context space. Use these to understand the full scope of the work done:

COMPACT_SUMMARIES
{{/IF COMPACT_SUMMARIES}}

## Your Task

Reflect on THIS conversation (the one you're currently in){{#IF COMPACT_SUMMARIES}} and the previous context above{{/IF COMPACT_SUMMARIES}}, and generate a concise summary focused on:

1. **Key Insights**: What important learnings emerged during implementation?
2. **Decisions Made**: What significant technical decisions were made and why?
3. **Challenges Encountered**: What obstacles were faced and how were they resolved?
4. **Mistakes and Corrections**: What mistakes were made and what was learned from them?

## Output Format

**CRITICAL: Your entire output will be posted DIRECTLY as a comment on the issue. Do NOT include:**
- Any meta-commentary about the summary (e.g., "This summary is ready to be posted...")
- Any preamble or introduction before the markdown
- Any explanation of what you're doing
- Any text after the closing `</details>` tag

**Output ONLY the markdown content below, starting with `## iloom Session Summary` and ending with `</details>`.**

Structure it with key themes visible at the top, then detailed sections wrapped in collapsible tags:

```markdown
## iloom Session Summary

**Key Themes:**
- [Theme 1 - one sentence]
- [Theme 2 - one sentence]
- [Theme 3 - one sentence]

---

<details>
<summary>Session Details (click to expand)</summary>

### Key Insights
- [Insight 1]
- [Insight 2]

### Decisions Made
- [Decision and rationale]

### Challenges Resolved
- [Challenge and resolution]

### Lessons Learned
- [What could be done better next time]

</details>

Keep the visible themes section brief (3-5 bullet points, one sentence each). The detailed sections inside the collapsible can be more comprehensive. Focus on information that would help future developers or AI agents working on similar tasks.

REMINDER: Output ONLY the markdown. No commentary before or after. Your response IS the comment.

</details>

## Detailed Execution Order

### Phase 1: Transcript Reader Utility
1. Create `/src/utils/claude-transcript.ts` with transcript reading functions -> Verify: TypeScript compiles
2. Create `/src/utils/claude-transcript.test.ts` with unit tests -> Verify: Tests pass

### Phase 2: PromptTemplateManager Update
1. Edit `/src/lib/PromptTemplateManager.ts:36` - Add `COMPACT_SUMMARIES` to interface -> Verify: TypeScript compiles

### Phase 3: Prompt Template Update
1. Edit `/templates/prompts/session-summary-prompt.txt` - Add conditional compact summaries section -> Verify: File saved

### Phase 4: SessionSummaryService Integration
1. Edit `/src/lib/SessionSummaryService.ts:12` - Add import for transcript utils -> Verify: TypeScript compiles
2. Edit `/src/lib/SessionSummaryService.ts:82-87` - Add transcript reading in `generateAndPostSummary()` -> Verify: TypeScript compiles
3. Edit `/src/lib/SessionSummaryService.ts:151-156` - Add transcript reading in `generateSummary()` -> Verify: TypeScript compiles
4. Update `/src/lib/SessionSummaryService.test.ts` - Add transcript integration tests -> Verify: Tests pass

### Phase 5: Build and Verification
1. Run `pnpm build` -> Verify: Build succeeds
2. Run `pnpm test` -> Verify: All tests pass

**NOTE:** Follow TDD approach - write tests before implementation for each component.

## Dependencies and Configuration

None - uses existing node:fs/promises, node:os, node:path modules.

</details>

[acreeger]

Implementation Complete - Issue #308 - Session Transcript Enhancement

Summary

Enhanced session summary generation by reading Claude Code transcript files to extract compact summaries (pre-compaction context) and passing them as additional context to the summary generation prompt. This solves the problem where --resume <sessionId> only provides post-compaction context, losing valuable conversation history.

Changes Made

• claude-transcript.ts (NEW): Utility to read and parse Claude Code transcript JSONL files
• PromptTemplateManager.ts: Added COMPACT_SUMMARIES variable and conditional processing
• session-summary-prompt.txt: Updated to include compact summaries section when available
• SessionSummaryService.ts: Integrated transcript reading before Claude invocation

Validation Results

• Tests: 2837 passed (including 19 new transcript utility tests + 3 new service tests)
• Typecheck: Passed
• Lint: Passed
• Build: Passed

---

Detailed Changes by File (click to expand)

Files Created

/src/utils/claude-transcript.ts (NEW)

Purpose: Read and parse Claude Code session transcript files

• getClaudeProjectPath(): Encodes worktree path to Claude projects directory format
• findSessionTranscript(): Locates transcript file for worktree and session ID
• extractCompactSummaries(): Parses JSONL and extracts entries with isCompactSummary: true
• readSessionContext(): Main entry point that returns formatted compact summaries or null

/src/utils/claude-transcript.test.ts (NEW)

Purpose: Unit tests for transcript reading utilities (19 tests)

• Tests path encoding, transcript discovery, JSONL parsing, and error handling

Files Modified

/src/lib/PromptTemplateManager.ts

Changes: Added COMPACT_SUMMARIES variable support

• Line 37: Added COMPACT_SUMMARIES to TemplateVariables interface
• Lines 210-212: Added variable substitution for COMPACT_SUMMARIES
• Lines 325-334: Added conditional processing for {{#IF COMPACT_SUMMARIES}}

/templates/prompts/session-summary-prompt.txt

Changes: Added conditional compact summaries section

• Lines 8-14: Added {{#IF COMPACT_SUMMARIES}} block with context explanation
• Line 18: Updated task description to reference compact summaries when available

/src/lib/SessionSummaryService.ts

Changes: Integrated transcript reading into summary generation

• Line 13: Added import for readSessionContext
• Lines 83-87: Added transcript reading in generateAndPostSummary()
• Lines 159-163: Added transcript reading in generateSummary()
• Updated template variables to include COMPACT_SUMMARIES

/src/lib/SessionSummaryService.test.ts

Changes: Added tests for transcript integration

• Added mock for readSessionContext
• Updated existing tests to expect COMPACT_SUMMARIES variable
• Added 3 new tests: compact summaries in prompt, working without summaries, handling errors

Test Coverage Added

• /src/utils/claude-transcript.test.ts: 19 tests covering all utility functions
• /src/lib/SessionSummaryService.test.ts: 3 additional tests for transcript integration

Dependencies Added

None - uses existing node:fs/promises, node:os, node:path modules

[acreeger]

iloom Session Summary

Key Themes:

• Implemented automatic session summary generation with transcript reading to preserve pre-compaction conversation context
• Made summary model configurable via settings with schema-driven defaults, avoiding hardcoded values throughout codebase
• Evolved from complex phrase-based failure detection to simple length-based validation for robustness
• Moved session ID generation responsibility into service layer following architectural feedback
• Created comprehensive integration with both il finish (automatic) and il summary (manual) workflows

---

Session Details (click to expand)

Key Insights

• Claude Code transcript storage architecture: Sessions stored at ~/.claude/projects/{encoded-path}/{sessionId}.jsonl where path encoding replaces both / and _ with - (not just slashes)
• Compact summaries are preserved: Pre-compaction conversation context available in JSONL via isCompactSummary: true entries (~11K chars each), enabling full-session summaries even after compaction
• Schema-driven defaults pattern: Using Schema.parse({}).field with Zod prevents default values from littering codebase and ensures single source of truth
• Simple validation beats complex heuristics: Length-based validation (< 100 chars) proved more robust than phrase matching which suffered from false positives
• Service layer owns domain logic: Session ID generation belongs in SessionSummaryService, not command layer - "that's a smell" feedback led to proper refactoring
• Documentation strategy: Main README focuses on automatic behavior and features, detailed command reference lives in docs/iloom-commands.md
• Non-blocking optional features: Summary generation enhances workflow but must never block il finish completion

Decisions Made

• Default summary model to sonnet: User explicitly requested sonnet over haiku for better quality summaries, configurable via summary.model setting
• Read compact summaries from transcripts: Extract and include pre-compaction context directly in prompt rather than relying solely on --resume <sessionId>
• Conditional template sections: Use {{#IF COMPACT_SUMMARIES}} pattern to include previous context only when available, with explicit usage instructions
• Length-based failure detection: After false positives with "conversation history" appearing in valid summaries, switched to summary.length < 100 check
• Service-layer session ID generation: Moved deterministic UUID v5 generation from command layer into SessionSummaryService after architectural feedback
• Dry-run preview in finish command: Generate summary but show only first 100 chars preview instead of posting
• Removed phrase-based error detection: User feedback "can we get rid of that error handling temporarily" led to simpler, more reliable approach
• Summary model documented in iloom-commands.md: Line 496 incorrectly states "haiku model" - should reflect actual configurable model (default: sonnet)

Challenges Resolved

• Path encoding mismatch: Original regex /\//g only replaced slashes; Claude Code also replaces underscores - fixed to /[/_]/g after user discovered fallback message despite transcript existing
• False positive failure detection: Phrases like "conversation history" triggered fallback on valid summaries - initially tried more specific phrases, user suggested simpler length-based approach
• Test failures after validation change: Mock returned short summary failing new < 100 chars validation - updated mock to return realistic >100 char summary
• Prompt clarity for compact summaries: Initial prompt didn't explain how to use previous context - added explicit "CRITICAL: How to use this section" instructions
• Meta-commentary in output: Claude outputting "This summary is ready to be posted..." - strengthened prompt with CRITICAL warnings about outputting ONLY markdown
• Architectural smell in session ID handling: Started in command layer, user feedback led to proper refactoring into service layer where domain logic belongs
• Documentation accuracy: iloom-commands.md line 496 states "haiku model" but should reflect configurable model setting

Lessons Learned

• Investigate before assuming: Path encoding required investigation to discover both / and _ replacement, assumptions would have missed the underscore case
• Simple heuristics over pattern matching: Length checks avoid false positive complexity inherent in phrase detection
• Schema-driven defaults keep code DRY: The Schema.parse({}).field pattern eliminates scattered default values
• Listen to architectural "smells": User feedback like "that's a smell" often points to valuable refactoring opportunities
• Debug logging is essential early: Added logger.debug() for troubleshooting complex integrations with external tools like Claude Code
• Template documentation matters: Clear instructions in prompts prevent confusion about how to use provided context
• Documentation belongs in two places: Quick reference in README.md for discovery, detailed reference in dedicated commands documentation
• User feedback drives simplification: "Can we get rid of that error handling" and "why don't we do a length based one" led to more robust implementation
• Documentation review needed: Found inaccuracy in iloom-commands.md line 496 stating "haiku model" when default is actually "sonnet" and configurable