Task Wrapup

Task Wrap-Up Skill

Comprehensive work session wrap-up orchestrator for professional project communication and record-keeping.

Purpose

Automate end-of-session workflows by:

• Generating intelligent work summaries from git commits, todos, and file changes
• Sending notifications to stakeholders via email, SMS, and Slack
• Logging billable hours to worklog system
• Updating project documentation
• Optional calendar and GitHub integration

When to Use

Trigger this skill when:

• Ending a work session and need to communicate progress
• Completing a feature or milestone
• Wrapping up before context switch to different project
• Need to bill time and update stakeholders simultaneously
• Keywords: "wrap up", "end session", "send update", "log work"

Core Workflow

Phase 1: Configuration Check

1. Check for config file: Look for .task_wrapup_skill_data.json in current working directory
2. Create if missing: If not found, prompt user for:
   • Project name
   • Email recipients (first name, last name, email address)
   • SMS recipients (first name, last name, phone number)
   • Slack channel (optional)
   • Worklog settings
3. Validate config: Ensure all required fields present and properly formatted

Phase 2: Summary Generation

1. Analyze work session:
   • Git commits from last 12 hours
   • File changes and statistics
   • TodoWrite completed tasks (if available)
   • Serena session memory (if available)
2. Generate summaries:
   • Full summary: Detailed description for email and Slack
   • Concise summary: Brief version for SMS and worklog (≤300 chars)
3. User override: Allow user to provide custom summary text instead

Phase 3: Preview & Confirmation

1. Display preview:

   • Show generated summary content
   • Display distribution plan (who gets what)
   • List all configured channels and their status

2. 🚨 CRITICAL: ASK THESE FOUR QUESTIONS EVERY TIME (Non-negotiable, always required):

   These questions MUST be asked in EVERY task-wrapup execution, before proceeding to Phase 4:

   Question 1 - Git Commit:

   Would you like to commit changes to git before sending notifications? (y/n)
   
   This will create a commit with:
   - All uncommitted changes in working directory
   - Commit message based on session summary
   - Timestamp and completion marker
   

   Question 2 - Create Pull Request:

   Would you like to create a pull request for this feature branch? (y/n)
   
   This will:
   - Push feature branch to remote repository
   - Create pull request targeting parent branch (from session state)
   - Use session summary as PR description
   - Optionally checkout parent branch after creation
   - Automatically clean up session state file
   
   Note: Requires .task_session_state.json file from task-start skill.
         If session state is missing, will use default parent branch.
   

   Question 3 - Calendar:

   Would you like to create a calendar event or reminder? (y/n)
   
   Options:
   - Create event for deliverable/milestone
   - Set reminder for follow-up tasks
   - Schedule next work session
   

   Question 4 - GitHub:

   Would you like to create a GitHub issue or release notes? (y/n)
   
   Options:
   - Create issue for follow-up work
   - Draft release notes for version
   - Update existing issue with session notes
   

   ENFORCEMENT RULES:

   • ✅ Ask ALL FOUR questions EVERY TIME
   • ✅ Ask even if user said "continue without questions" (these are decision points, not clarifications)
   • ✅ Ask even if config has features disabled
   • ✅ Ask even if user didn't mention them
   • ✅ Ask even if user previously declined
   • ❌ NEVER skip these questions to "save time"
   • ❌ NEVER assume the answer is "no"
   • ❌ NEVER proceed to Phase 4 without explicit answers

   PURPOSE: These serve as critical checkpoints to ensure:

   • Work is properly committed to version control
   • Pull requests created for feature branches
   • Important dates/deadlines are calendared
   • Follow-up work is tracked in GitHub

   Default to "no" only if user explicitly declines each question.

3. Confirmation options (AFTER the four mandatory questions):

   • [1] Send as-is
   • [2] Edit summary
   • [3] Customize per channel (different content for email vs SMS vs Slack)
   • [4] Modify distribution (enable/disable channels)
   • [5] Cancel operation

4. Handle user choice: Process edits and modifications as requested

Phase 4: Parallel Dispatch

Execute notifications in parallel for speed:

Email (via @~/.claude/skills/email/SKILL.md):

• Send to all recipients as group email
• Uses seasonal HTML formatting
• Includes full summary with detail
• Automatic BCC to arlenagreer@gmail.com for multi-recipient

SMS (via @~/.claude/skills/text-message/SKILL.md):

• Send individual messages to each recipient (NEVER group text)
• Uses natural, humanized style - like sending a quick progress note to a colleague
• Tone: Friendly, professional, conversational but concise (≤320 chars)
• Think: "Just finished up X, got Y done, moving on to Z" not "Completed: X. Achieved: Y."
• Removes apostrophes for AppleScript compatibility

SMS Style Examples:

❌ Sterile: "Completed infrastructure modernization. Dependencies upgraded Ruby 3.4, Node 25. Fixed production deployment issues. Database migrations implemented."

✅ Natural: "Just wrapped up infrastructure work - upgraded to Ruby 3.4 and Node 25, fixed the production deployment blockers, and got database migrations sorted. Good progress today!"

❌ Sterile: "Implemented task coverage. Created 36 test files. Achieved 90% coverage target."

✅ Natural: "Finished the test coverage push - created 36 new test files and hit our 90% target. Feels good to have that wrapped up!"

Slack (if configured):

• Post to specified channel
• Uses full summary (same detail as email)
• Include @mentions if configured

Worklog (via @~/.claude/skills/worklog/SKILL.md):

• Create billable hours entry
• Uses concise summary as description
• CRITICAL: Check system clock for current date before logging
• Prompt for duration if configured, or use default
• Associate with project/client name from config

Documentation (via /sc:document):

• Script Phase: Creates documentation update request file (.task_wrapup_doc_update_request.md)
• Claude Code Phase: Detects request file and invokes /sc:document command
• Updates: CHANGELOG.md (session entry), README.md (affected sections), other configured paths
• Strategy: Uses smart_merge to intelligently integrate changes
• Summary: Documentation changes included in final wrap-up report

Calendar (optional, via @~/.claude/skills/calendar/SKILL.md):

• Only if user confirms during prompt (ALWAYS ask in Phase 3)
• Create calendar event or reminder
• CRITICAL: Be date-aware, check system clock

GitHub (optional, via /sc:git):

• Only if user confirms during prompt (ALWAYS ask in Phase 3)
• Create issue, PR, or release notes

OmniFocus (automatic, if configured):

• Completes OmniFocus task created during session startup
• Reads task ID from .task_session_state.json
• Marks task as complete via OmniFocus skill
• CRITICAL: Session lifecycle completion - tasks created at startup are automatically completed at wrapup
• Only runs if omnifocus.auto_log_tasks is enabled in config
• Skips gracefully if task ID not found in session state
• Non-blocking: continues even if completion fails

Commit Changes (optional):

• Only if user confirms during prompt (ALWAYS ask in Phase 3)
• Commit documentation updates to git
• Use descriptive commit message based on session summary

Phase 5: Final Summary

Display comprehensive results:

• ✅ Success indicators for completed actions
• ❌ Error indicators with details for failures
• ⏭️ Skip indicators for disabled channels
• Summary statistics (total, successful, failed)
• Detailed error messages for troubleshooting

Configuration Schema

Configuration stored in .task_wrapup_skill_data.json in project directory:

{
  "schema_version": "1.0",
  "project_name": "MyProject",
  "created_at": "2025-01-15T10:30:00",
  "last_updated": "2025-01-15T10:30:00",

  "summary_generation": {
    "strategy": "hybrid",
    "sources": {
      "git_commits": true,
      "todo_tasks": true,
      "serena_memory": true,
      "file_changes": true
    },
    "intelligence": {
      "extract_key_decisions": true,
      "identify_blockers": true,
      "highlight_risks": true,
      "include_metrics": false
    }
  },

  "communication": {
    "email": {
      "enabled": true,
      "recipients": [
        {"first_name": "John", "last_name": "Doe", "email": "john@example.com"}
      ],
      "cc": [],
      "template": "professional",
      "include_attachments": false
    },
    "sms": {
      "enabled": true,
      "recipients": [
        {"first_name": "Jane", "last_name": "Smith", "phone": "+15551234567"}
      ],
      "max_length": 320,
      "critical_only": false
    },
    "slack": {
      "enabled": false,
      "channel": "",
      "mention_users": [],
      "thread_mode": "new_message"
    }
  },

  "worklog": {
    "enabled": true,
    "prompt_for_duration": true,
    "default_duration_minutes": null,
    "round_to_nearest": 15,
    "date_handling": {
      "prompt_for_date": false,
      "default": "today",
      "timezone": "America/New_York"
    }
  },

  "documentation": {
    "enabled": true,
    "auto_update": true,
    "paths": ["README.md"],
    "strategy": "smart_merge",
    "commit_changes": false
  },

  "pull_request": {
    "enabled": true,
    "default_parent_branch": "develop",
    "auto_checkout_parent": true,
    "cleanup_session_state": true,
    "draft": false,
    "title_template": null,
    "body_template": null
  },

  "optional_actions": {
    "calendar": {
      "enabled": false,
      "prompt_by_default": false
    },
    "github": {
      "enabled": false,
      "prompt_by_default": false
    }
  },

  "execution": {
    "preview_before_send": true,
    "parallel_execution": true,
    "max_retries": 3,
    "retry_delay_seconds": 5
  },

  "omnifocus": {
    "project_name": "Development",
    "auto_log_tasks": true,
    "prompt_if_missing": true
  }
}

Pull Request Configuration

The pull_request section controls PR automation behavior:

• enabled (boolean, default: true): Enable/disable PR creation prompts during task wrapup
• default_parent_branch (string, default: "develop"): Fallback parent branch when session state unavailable
• auto_checkout_parent (boolean, default: true): Automatically checkout parent branch after successful PR creation
• cleanup_session_state (boolean, default: true): Delete .task_session_state.json after successful PR workflow
• draft (boolean, default: false): Create PRs as draft by default
• title_template (string|null, default: null): Custom PR title template (uses session summary if null)
• body_template (string|null, default: null): Custom PR body template (uses session summary if null)

Session State Integration:

• PR automation depends on .task_session_state.json created by task-start skill
• Session state contains: feature branch, parent branch, issue number, GitHub issue metadata
• If session state missing: Uses default_parent_branch for PR targeting
• Session state location: Project root directory
• Session state cleanup: Automatic after successful PR creation (configurable)

Workflow:

1. User confirms PR creation in Phase 3 Question 2
2. System reads .task_session_state.json for parent branch
3. Pushes feature branch to remote repository
4. Creates PR via GitHub CLI (gh pr create)
5. Uses session summary as PR description
6. Optionally checks out parent branch
7. Cleans up session state file

OmniFocus Configuration

The omnifocus section controls automatic task completion integration:

• project_name (string|null, default: null): OmniFocus project name for task management
• auto_log_tasks (boolean, default: true): Enable/disable automatic task completion during wrapup
• prompt_if_missing (boolean, default: true): Prompt user if project name not configured

Session Lifecycle Integration:

• Tasks are automatically created during session startup by task-startup skill
• Task ID stored in .task_session_state.json for lifecycle tracking
• Task-wrapup skill completes the OmniFocus task using stored task ID
• Bidirectional workflow: startup creates → wrapup completes

Configuration Commands:

# Set OmniFocus project for this directory
python3 scripts/config_manager.py set-omnifocus --omnifocus-project "Development"

# Get current OmniFocus project
python3 scripts/config_manager.py get-omnifocus

Workflow:

1. Session state loaded from .task_session_state.json
2. OmniFocus task ID extracted from session state
3. Task completion executed via OmniFocus skill integration
4. Task marked as complete in OmniFocus
5. Non-blocking: continues even if completion fails

Requirements:

• OmniFocus skill installed at ~/.claude/skills/omnifocus/
• OmniFocus project configured via config_manager.py
• Session state file exists (created by task-startup skill)

Bundled Resources

Python Scripts

scripts/config_manager.py

• Handles CRUD operations for configuration file
• Auto-migration from older schema versions
• Validation of configuration structure
• CLI: create, show, validate, add-recipient, remove-recipient

scripts/summary_generator.py

• Generates intelligent summaries from multiple sources
• Git commit analysis (last 12 hours)
• File change statistics
• Key point extraction from commit messages
• Full and concise summary generation
• CLI: --config, --user-input, --format (full/concise/json)

scripts/preview_interface.py

• Interactive preview and confirmation workflow
• Summary and distribution plan display
• Edit, customize, and modify options
• User confirmation before sending
• CLI: --summary, --config

scripts/notification_dispatcher.py

• Orchestrates parallel execution across all channels
• Email, SMS, Slack, worklog, documentation dispatch
• Optional calendar, GitHub, and OmniFocus integration
• Automatic OmniFocus task completion using stored task IDs
• Comprehensive error handling and reporting
• CLI: --summary, --config, --sequential (optional)

Extension Architecture

Core Extensions (extensions/core/):

• Email integration (required)
• SMS integration (required)
• Worklog integration (required)

Optional Extensions (extensions/optional/):

• Slack integration
• Calendar integration
• GitHub integration
• OmniFocus integration
• Documentation updates

Future Extensions (extensions/future/):

• Discord notifications
• Microsoft Teams
• JIRA updates
• Asana task creation
• Linear integration

Usage Examples

Basic Usage

User: "Wrap up this session"

The skill will:

1. Check for .task_wrapup_skill_data.json in current directory
2. If not found, prompt for configuration
3. Generate summary from git commits
4. Show preview and get confirmation
5. Send notifications in parallel
6. Display final summary

Custom Summary

User: "Wrap up with custom summary: Completed authentication system with OAuth2, added tests, updated docs"

Uses user-provided summary instead of auto-generated.

Quick Worklog Only

User: "Just log my work time for this session"

Disable email/SMS in config, enable only worklog.

With Calendar Event

User: "Wrap up and create calendar reminder for tomorrow's demo"

Triggers optional calendar integration.

Configuration Management

Create New Config

python3 scripts/config_manager.py create --project-name "MyProject" --directory .

Show Current Config

python3 scripts/config_manager.py show --directory .

Validate Config

python3 scripts/config_manager.py validate --directory .

Add Email Recipient

python3 scripts/config_manager.py add-recipient \
  --type email \
  --first-name John \
  --last-name Doe \
  --contact john@example.com

Add SMS Recipient

python3 scripts/config_manager.py add-recipient \
  --type sms \
  --first-name Jane \
  --last-name Smith \
  --contact +15551234567

Error Handling

Missing Config

• Symptom: No .task_wrapup_skill_data.json found
• Action: Prompt user for configuration information
• Recovery: Create new config with user input

Email Failure

• Symptom: Email skill returns error
• Action: Log error details in final summary
• Recovery: Prompt user for manual correction, continue with other channels

SMS Failure

• Symptom: Text-message skill returns error
• Action: Log which recipients failed
• Recovery: Display phone numbers for manual retry

Worklog Failure

• Symptom: Worklog skill returns error
• Action: Display error and worklog details
• Recovery: Offer to retry or skip

Date Awareness Issues

• Symptom: Incorrect date for worklog or calendar
• Prevention: Always check system clock before date operations
• Recovery: Prompt user to specify date manually

Documentation Update Workflow

Two-Phase Process

Phase 1: Script Execution (Python)

1. notification_dispatcher.py creates .task_wrapup_doc_update_request.md
2. File contains session summary, target paths, update strategy
3. Returns success with path to request file

Phase 2: Claude Code Execution (After script completes)

1. Detection: Check for .task_wrapup_doc_update_request.md in current directory
2. Reading: Read the request file to extract session summary and targets
3. Invocation: Execute /sc:document with the session summary
4. Updates: /sc:document updates CHANGELOG.md, README.md, and other paths
5. Cleanup: Remove .task_wrapup_doc_update_request.md after processing
6. Reporting: Include documentation updates in final wrap-up summary

Claude Code Responsibilities

When task-wrapup skill completes, Claude Code should:

# 1. Check for documentation update request
request_file = ".task_wrapup_doc_update_request.md"
if os.path.exists(request_file):
    # 2. Read the request
    with open(request_file, 'r') as f:
        request_content = f.read()

    # 3. Invoke /sc:document
    # Use SlashCommand tool to execute:
    # /sc:document --target CHANGELOG.md README.md --strategy smart_merge

    # 4. Report what was updated
    # "Updated CHANGELOG.md with session entry, refreshed README.md installation section"

    # 5. Cleanup
    os.remove(request_file)

Important Distinctions

/sc:document (Documentation Generation):

• ✅ Updates project documentation (CHANGELOG, README, API docs)
• ✅ Intelligently merges new information into existing docs
• ✅ Used by task-wrapup skill for documenting session work

/sc:save (Session Context Persistence):

• ❌ NOT for documentation updates
• ✅ Saves work context to Serena MCP for cross-session continuity
• ✅ Different purpose: session memory, not project docs

Critical Implementation Details

Phone Format (SMS)

• Requirement: E.164 format (+1XXXXXXXXXX)
• Validation: Ensure all phone numbers properly formatted
• Integration: Use contacts skill for phone lookup by name

Group vs Individual Messages

• Email: Can send to multiple recipients as group
• SMS: MUST send individually to each recipient (NEVER group text)
• Slack: Single message to channel (with optional @mentions)

Date Handling

• Worklog: ALWAYS check system clock for current date
• Calendar: Be aware of relative dates ("tomorrow", "next week")
• Include weekends: No business-day filtering

Configuration Scope

• Per-project: Each project has its own .task_wrapup_skill_data.json
• Not global: Configuration NOT stored in ~/.claude/skills/
• Git-aware: Add to .gitignore to avoid committing sensitive data

Integration with Other Skills

Email Skill

• Invoked via: @~/.claude/skills/email/SKILL.md
• Provides: Seasonal theming, authentic writing style, contact lookup
• OAuth token: Shared at ~/.claude/.google/token.json

Text-Message Skill

• Invoked via: @~/.claude/skills/text-message/SKILL.md
• Provides: AppleScript automation, contact lookup
• Requirements: macOS, Messages app permissions

Worklog Skill

• Invoked via: @~/.claude/skills/worklog/SKILL.md
• Provides: Time tracking, client billing
• Data: ~/.claude/skills/worklog/worklog.json

Calendar Skill

• Invoked via: @~/.claude/skills/calendar/SKILL.md
• Provides: Event creation, reminder setting
• Optional: Only if user requests

Contacts Skill

• Integration: Automatic contact lookup for email and SMS
• Resolves names to email addresses and phone numbers

Version History

v1.1.0 (2025-01-15)

• Documentation Integration: Implemented proper /sc:document integration
• Two-Phase Workflow: Script creates request file, Claude Code processes with /sc:document
• Smart Updates: CHANGELOG.md and README.md intelligently updated based on session
• Request File: .task_wrapup_doc_update_request.md for Claude Code detection
• Clarified Commands: Distinguished /sc:document (docs) from /sc:save (session context)
• Added Documentation: DOCUMENTATION_INTEGRATION.md with comprehensive guide

v1.0.0 (2025-01-15)

• Initial release
• Core features: email, SMS, Slack, worklog, documentation
• Intelligent summary generation from git commits
• Interactive preview and confirmation workflow
• Parallel notification dispatch
• Per-project configuration with auto-migration
• Extension plugin architecture

Future Enhancements

Planned Features

• Discord integration
• Microsoft Teams notifications
• JIRA issue creation
• Asana task updates
• Linear integration
• Notion page updates

Potential Improvements

• TodoWrite integration for completed tasks
• Serena memory integration for session context
• AI-powered summary enhancement
• Template customization per recipient
• Scheduling for delayed send
• Retry logic with exponential backoff

Author: Claude Code SuperClaude Framework License: MIT Repository: ~/.claude/skills/task-wrapup/