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IdlerGear Release Roadmap & Milestone Reorganization

Current State (January 2026)

  • Current Version: v0.6.0
  • Open Issues: 5 (all for future milestones)
  • Completed Milestones: v0.4.0, v0.5.0, v0.6.0 (original), v0.7.0 (original)
  • Active Milestones: v0.6.0 (in progress), v0.7.0 (planned), v0.8.0 (5 issues), v0.9.0 (planned)
  • Recent Completions: File Registry core (#287-289, #294), AI Assistant Integrations (#299, #300)

Problem Analysis

Issues

  1. Milestone bloat: Completed milestones (v0.4-v0.7) still open
  2. Version gap: Current version 0.5.4, but next milestone is v0.8.0
  3. Unorganized work: 15 critical issues have no milestone
  4. No epics: Large features not properly grouped
  5. Missing release dates: No target dates for planning
  6. Project board outdated: Doesn't reflect current priorities

Opportunities

  1. File Registry is ready to implement (10 detailed tasks)
  2. Clear feature groupings emerging
  3. Good balance of near-term and long-term work

New Release Structure

Release Philosophy

  • Minor releases (0.x.0): Every 2-3 months with major features
  • Patch releases (0.x.y): As needed for bug fixes
  • Stable v1.0: When core feature set is complete and battle-tested

Release Cadence

  • Q1 2026 (March): v0.6.0 - File Registry & Quality
  • Q2 2026 (June): v0.7.0 - GitHub Integration
  • Q3 2026 (September): v0.8.0 - Session Management Advanced
  • Q4 2026 (December): v0.9.0 - Multi-Assistant & Collaboration
  • Q1 2027 (March): v0.10.0 - Polish & Maturity

v0.6.0 - File Registry & Quality

Target: March 1, 2026 (6 weeks) Theme: Major new feature + quality improvements Status: In Progress - Core features completed, advanced features remain

Epic: File Registry & Deprecated File Detection (#286)

Problem: AI assistants access outdated/archived files causing bugs Solution: Explicit registry with MCP interception Priority: HIGH - Solves critical user pain point

Phase 1: Core Infrastructure (Weeks 1-2) ✅ COMPLETED

  • ✅ #287: FileRegistry data model and storage (HIGH, Medium effort) - Implemented in file_registry.py
  • ✅ #288: CLI commands for registry management (HIGH, Medium effort) - 7 commands in cli.py
  • ✅ #289: MCP tools for AI assistant access (HIGH, Small effort) - 8 MCP tools in mcp_server.py

Phase 2: MCP Interception (Weeks 2-3)

  • #290: MCP tool interception for file operations (HIGH, Large effort) ⭐ Critical

Phase 3: Multi-Agent Coordination (Week 4)

  • #291: Daemon integration for registry broadcasts (MEDIUM, Medium effort)

Phase 4: Auto-Detection & Polish (Weeks 5-6)

  • #292: Auto-detection scanner (LOW, Medium effort)
  • #293: Audit command (LOW, Small effort)
  • #295: Performance optimization (LOW, Small effort)

Phase 5: Testing & Documentation (Week 6)

  • #296: End-to-end integration testing (HIGH, Medium effort)
  • ✅ #294: User guide and documentation (MEDIUM, Small effort) - Comprehensive docs created

AI Assistant Integrations ✅ LARGELY COMPLETED

  • ✅ #299: Cursor AI IDE Integration - .mdc rules generation complete
  • ✅ #300: Aider Configuration - .aider.conf.yml generation complete
  • ⚠️ #298: GitHub Copilot CLI Integration - Template complete, MCP testing pending
  • ✅ Gemini CLI - GEMINI.md enhanced with comprehensive guidance
  • ✅ Goose - .goosehints integration complete
  • ✅ AGENTS.md - Enhanced with comprehensive multi-assistant guidance (205 lines)

Quality Improvements

  • #285: Fix pipx installation support (HIGH priority)

Success Criteria

  • ✅ AI blocked from reading deprecated files 95% of time
  • ✅ Registry setup takes < 5 minutes
  • ✅ Changes propagate to all agents within 1 second
  • ✅ Performance overhead < 10ms per file operation
  • ✅ pipx installation works correctly

v0.7.0 - GitHub Integration

Target: June 1, 2026 (12 weeks from now) Theme: Enhanced GitHub workflow integration Status: Detailed design needed

GitHub Projects v2 Sync

  • #257: Feature Request: GitHub Projects v2 Integration (EPIC)
  • #282: Status column mapping for GitHub Projects (HIGH)
  • #283: Custom field sync for GitHub Projects (MEDIUM)
  • #284: Bidirectional sync for GitHub Projects (HIGH)

Dependencies

  • Requires stable v0.6.0 release
  • Needs GitHub Projects v2 API research

Success Criteria

  • ✅ Bidirectional sync with GitHub Projects v2
  • ✅ Custom fields mapped correctly
  • ✅ Status updates propagate both ways
  • ✅ No data loss during sync

v0.8.0 - Session Management Advanced

Target: September 1, 2026 (18 weeks from now) Theme: Advanced session capabilities Status: Design in progress

Epic: Advanced Session Management (#271)

  • #273: Session branching and merging (MEDIUM)
  • #274: Session knowledge harvesting (MEDIUM)
  • #275: Session analytics and monitoring (MEDIUM)
  • #279: Daemon integration for multi-client monitoring (MEDIUM)

Dependencies

  • Requires v0.6.0 (daemon registry integration)
  • Builds on v0.7.0 (project sync foundation)

Success Criteria

  • ✅ Branch/merge sessions without data loss
  • ✅ Harvest knowledge from completed sessions
  • ✅ Monitor multiple concurrent sessions
  • ✅ Analytics show session productivity metrics

v0.9.0 - Multi-Assistant & Collaboration

Target: December 1, 2026 (24 weeks from now) Theme: Multi-assistant orchestration Status: Research phase

Gemini Integration

  • #212: Implement Gemini CLI Slash Commands (MEDIUM)
  • #213: Enhanced Gemini Context in GEMINI.md (MEDIUM)
  • #214: Investigate Gemini CLI Lifecycle Hooks (LOW)

Multi-Assistant Support

  • #259: SKILLS.md and AGENTS.md support for all AI assistants (MEDIUM)
  • #262: Review AI assistant tools for IdlerGear integration (LOW)

Dependencies

  • Requires v0.8.0 (session management)
  • Needs Gemini API research

Success Criteria

  • ✅ Gemini integrated with full feature parity
  • ✅ SKILLS.md/AGENTS.md work across all assistants
  • ✅ Multiple assistants can coordinate on same project
  • ✅ Clear documentation for each supported assistant

v0.10.0 - Polish & Maturity

Target: March 1, 2027 (30 weeks from now) Theme: Pre-release maturity milestone Status: Preparing for eventual 1.0 after extended stability period

Polish & UX

  • #281: Expand 'idle*' standalone command pattern (LOW)
  • #258: Auto-mark managed files for exclusion (MEDIUM)
  • #255: External Command Queue for IPC (MEDIUM)
  • #256: Report issues to upstream with disclaimer (LOW)

Maturity Goals

  • ✅ All v0.9.0 features stable for 3+ months
  • ✅ 80%+ test coverage on core features
  • ✅ Comprehensive documentation
  • ✅ No critical bugs
  • ✅ Production validation at multiple sites
  • ✅ API stability improvements
  • ✅ Performance benchmarks established

Note: True v1.0 will come when production-ready, not on a fixed timeline.

Milestone Cleanup Actions

Close Completed Milestones

These milestones have 0 open issues and should be closed:

  • v0.4.0 Release (5 closed issues)
  • v0.5.0 - Planning & Foundation (7 closed issues)
  • v0.6.0 - Structured Information (3 closed issues)
  • v0.7.0 - Session Management Foundation (4 closed issues)

Delete Outdated Milestone

  • v0.8.0 - Session Management Advanced
    • Reason: Should be v0.8.0, not v0.8.0 (wrong version number)
    • Action: Move issues to new v0.8.0, delete old

Issue Prioritization Framework

Priority Levels

  • CRITICAL: Blocks release or causes data loss
  • HIGH: Major feature or significant bug
  • MEDIUM: Important but not blocking
  • LOW: Nice-to-have or future enhancement

Priority Assignment by Milestone

v0.6.0 (File Registry)

  • Critical: #290 (MCP interception - core feature)
  • High: #287, #288, #289, #296, #285
  • Medium: #291, #294
  • Low: #292, #293, #295

v0.7.0 (GitHub Integration)

  • High: #282, #284
  • Medium: #283

v0.8.0 (Session Management)

  • Medium: #273, #274, #275, #279
  • (Lower priority as it's further out)

v0.9.0 (Multi-Assistant)

  • Medium: #212, #213, #259
  • Low: #214, #262

v0.10.0 (Stable)

  • Medium: #255, #258
  • Low: #256, #281

Epic Structure

What is an Epic?

Large features that span multiple issues and require coordination.

Epic Label Creation

Create label: epic (color: #5319e7, description: "Large feature spanning multiple issues")

Current Epics

  1. Epic #286: File Registry & Deprecated File Detection System

    • Sub-tasks: #287-#296 (10 issues)
    • Milestone: v0.6.0
    • Owner: Core team
    • Status: Ready to implement

  2. Epic #271: Advanced Session Management

    • Sub-tasks: #273-#275, #279 (4 issues)
    • Milestone: v0.8.0
    • Owner: TBD
    • Status: Design phase

  3. Epic #257: GitHub Projects v2 Integration

    • Sub-tasks: #282-#284 (3 issues)
    • Milestone: v0.7.0
    • Owner: TBD
    • Status: Needs design

Future Epics (Create Later)

  • Multi-Assistant Coordination (v0.9.0)
  • Knowledge Graph Enhancement
  • Test Automation System

GitHub Project Board Structure

Recommended Structure

Option 1: Single Unified Board

Project Name: "IdlerGear Development Roadmap"

Columns:

  • 📋 Backlog (no milestone or v1.0+)
  • 🎯 Current Sprint (v0.6.0 high priority)
  • 🚧 In Progress
  • 👀 In Review
  • ✅ Done (last 2 weeks)

Views:

  • By Milestone (grouped)
  • By Epic (filtered)
  • By Priority (sorted)
  • Current Sprint (v0.6.0 only)

Option 2: Per-Release Boards

  • v0.6.0 - File Registry & Quality
  • v0.7.0 - GitHub Integration
  • v0.8.0 - Session Management Advanced
  • v0.9.0 - Multi-Assistant & Collaboration
  • v0.10.0 - Stable Release

Recommendation: Option 1 (single board) for better overview

Implementation Steps

Phase 1: Cleanup (Today)

  1. ✅ Close completed milestones (v0.4.0, v0.5.0, v0.6.0, v0.7.0)
  2. ✅ Create epic label
  3. ✅ Tag epic issues (#286, #271, #257)

Phase 2: Milestone Restructure (Today)

  1. ✅ Create/update v0.6.0 milestone with target date March 1, 2026
  2. ✅ Create/update v0.7.0 milestone with target date June 1, 2026
  3. ✅ Update v0.8.0 milestone with target date September 1, 2026
  4. ✅ Update v0.9.0 milestone with target date December 1, 2026
  5. ✅ Update v0.10.0 milestone with target date March 1, 2027

Phase 3: Issue Organization (Today)

  1. ✅ Assign all File Registry issues (#286-296) to v0.6.0
  2. ✅ Assign #285 to v0.6.0
  3. ✅ Assign GitHub Projects issues (#257, #282-284) to v0.7.0
  4. ✅ Keep session management (#271, #273-275, #279) in v0.8.0
  5. ✅ Keep Gemini/multi-assistant (#212-214, #259, #262) in v0.9.0
  6. ✅ Keep polish features (#255, #256, #258, #281) in v0.10.0

Phase 4: Priority Update (Today)

  1. ✅ Update all v0.6.0 issues with priority labels
  2. ✅ Add "blocks: #XXX" comments for dependencies
  3. ✅ Update epic issues with task lists

Phase 5: Project Board (Today)

  1. ✅ Create new unified project board
  2. ✅ Add all open issues to board
  3. ✅ Configure views (milestone, epic, priority)
  4. ✅ Archive old project boards

Phase 6: Documentation (Today)

  1. ✅ Create ROADMAP.md in repo
  2. ✅ Update README.md with roadmap link
  3. ✅ Post announcement issue with roadmap

Success Metrics

Short-term (v0.6.0)

  • File Registry fully implemented and tested
  • No critical bugs in v0.6.0 release
  • Documentation complete
  • Release on time (March 1, 2026)

Medium-term (v0.7-0.9)

  • Each release delivers on schedule (±1 week)
  • No major rewrites needed
  • Community feedback incorporated
  • Test coverage stays above 80%

Long-term (v0.10.0)

  • Production deployments successful
  • API stable for 6+ months
  • Active community contributions
  • Clear upgrade path from pre-1.0

Communication Plan

Release Announcements

  • GitHub Releases with changelog
  • Update README.md with latest version
  • Post to discussions/social media
  • Email active users (if list exists)

Breaking Changes

  • Documented in CHANGELOG.md
  • Migration guide provided
  • Deprecated features warned for 1 release
  • Clear upgrade instructions

Feedback Channels

  • GitHub Issues for bugs/features
  • GitHub Discussions for questions
  • Direct communication with early adopters

Risks & Mitigation

Risk 1: Scope Creep

Mitigation: Strict milestone scope, move non-critical to next release

Risk 2: Delayed Dependencies

Mitigation: Parallel work where possible, fallback plans

Risk 3: Breaking Changes

Mitigation: Semantic versioning, deprecation warnings, migration guides

Risk 4: Quality vs Speed

Mitigation: Automated testing, code review, beta releases before stable

Next Actions

  1. Execute cleanup (Steps above)
  2. Start v0.6.0 work (Task #287)
  3. Weekly milestone review (Track progress)
  4. Monthly roadmap update (Adjust based on velocity)

Progress Summary (v0.5.19)

Completed in v0.5.x Series

  • ✅ File Registry Core (#287-289, #294): Data model, CLI, MCP tools, documentation
  • ✅ AI Assistant Integrations (#298-300): Cursor, Aider, Copilot, Gemini, Goose, AGENTS.md
  • ✅ Plugin System (v0.5.11-13): CLI commands, MCP tools, Mem0 integration
  • 🔄 v0.6.0 Status: ~60% complete (core done, MCP interception & testing remain)

Next Priorities

  1. #290: MCP tool interception (CRITICAL for File Registry)
  2. #296: End-to-end integration testing
  3. #285: Fix pipx installation support (HIGH priority bug)
  4. #291: Daemon integration for registry broadcasts

Last Updated: January 21, 2026 Next Review: February 1, 2026