Piper Morgan Roadmap - Sprint A7 Active (Expanded Scope)

Version: 10.0 Last Updated: October 22, 2025, 3:30 PM PDT Key Change: Sprint A6 complete, Sprint A7 expanded to 12 issues (4 categories), Sprint A8 added for Alpha prep

Vision Statement

To create the world’s most advanced AI-assisted development platform, enabling teams to build software with unprecedented intelligence, efficiency, and quality.

🐛 The Inchworm Protocol

Our Execution Methodology: Complete each epic 100% before moving to next. NO EXCEPTIONS.

Critical Principle: Even when we discover work is partially done (like the production handlers), we VERIFY everything systematically. No assumptions, no skipping.

Current Status (October 22, 2025)

✅ Completed Work

Phase 1: The Great Refactor (Sept 20 - Oct 8)

All GREAT epics complete with 99%+ verification

Phase 2: Complete the Build of CORE

Sprint A1: Critical Infrastructure ✅ (Oct 8-11)

Database migration (#113)
Test cache fixes (#216)
LLM configuration architecture (#217)
Intent classification enhancement (#212) - 98.62% accuracy achieved

CORE-CRAFT Superepic ✅ (Oct 11-14)

GAP: Infrastructure maturity (#232)
PROOF: Documentation precision (#233)
VALID: System verification (#234)
Discovery: 22 production handlers already implemented!

Sprint A2: Notion & Errors ✅ (Oct 15-16)

CORE-ERROR-STANDARDS (#215) - REST-compliant error handling across all endpoints
CORE-NOTN-API (#142) - Notion API connectivity fixed
CORE-NOTN-USER (#136) - Removed hardcoded values
CORE-NOTN-UP (#165) - Database API upgrade
CORE-INT (#109) - GitHub legacy deprecation

Sprint A3: Core Activation ✅ (Oct 17-19)

CORE-MCP-MIGRATION (#198) - Model Context Protocol adoption
CORE-ETHICS-ACTIVATE (#197) - Ethics middleware activated
CORE-KNOW (#99) - Knowledge graph connected to conversation
CORE-KNOW-BOUNDARY (#230) - Boundary enforcement implemented

Sprint A4: Standup Epic ✅ (Oct 19-20)

CORE-STAND-FOUND (#119) - Morning standup foundation
CORE-STAND-MODES-API (#162) - Multi-modal generation API
CORE-STAND-SLACK-REMIND (#161) - Slack reminder integration
CORE-STAND (#240) - Core daily standup functionality

Sprint A5: Learning System ✅ (Oct 20-21)

CORE-LEARN-A (#221) - Learning infrastructure foundation
CORE-LEARN-B (#222) - Pattern recognition (PatternType extensions)
CORE-LEARN-C (#223) - Preference learning (UserPreferenceManager)
CORE-LEARN-D (#224) - Workflow optimization (Chain-of-Draft)
CORE-LEARN-E (#225) - Intelligent automation (safety-first)
CORE-LEARN-F (#226) - Integration & polish, Learning Dashboard UI
CORE-LEARN (#220) - Parent epic complete

Sprint A6: User Infrastructure ✅ (Oct 9-22)

CORE-LLM-SUPPORT (#237) - Complete LLM provider integration (4 providers)
CORE-USERS-JWT (#227) - Token blacklist storage
CORE-USERS-PROD (#229) - Production database hardening (SSL/TLS)
CORE-USERS-API (#228) - Multi-user API key management with zero-downtime rotation
CORE-AUDIT-LOGGING (#249) - Comprehensive audit trail system
CORE-USERS-ONBOARD (#218) - Alpha user onboarding with setup wizard and health checks

Test Coverage: 100% passing across all sprints (250+ tests) Security: JWT blacklist, keychain integration, audit trail, SSL/TLS Performance: 602K req/sec sustained, <100ms API response

🔄 Currently Active

Position: Sprint A7 (Polish & Buffer) Sprint: A7 of 8 (penultimate Alpha sprint)

CORE Completion Path - Sprints A7-A8

Sprint A7: Polish & Buffer ➡️ (Oct 22-26)

Current Sprint - Expanded scope (12 issues across 4 categories)

1. CORE-UX (4 issues):

#254: CORE-UX-QUIET - Quiet startup mode (2h, Medium)
#255: CORE-UX-STATUS-USER - Status checker user detection (3h, Medium)
#256: CORE-UX-BROWSER - Auto-launch browser (1h, Low, Optional)
#248: CORE-PREF-CONVO - Conversational personality preferences (3-5h, Medium)

2. Critical Fixes (2 issues):

#257: CORE-KNOW-BOUNDARY-COMPLETE - Complete BoundaryEnforcer integration (2-3h)
#258: CORE-AUTH-CONTAINER - Fix JWT service dependency injection (2-3h)

3. CORE-KEYS (3 issues):

#250: CORE-KEYS-ROTATION-REMINDERS - Automated key rotation reminders (2-3h)
#252: CORE-KEYS-STRENGTH-VALIDATION - API key strength validation (2-3h)
#253: CORE-KEYS-COST-ANALYTICS - API cost tracking & usage analytics (2-3h)

4. CORE-ALPHA (3 issues):

#259: CORE-USER-ALPHA-TABLE - Create Alpha users table (1-2h)
#260: CORE-USER-MIGRATION - Alpha to production user migration tool (2-3h)
#261: CORE-USER-XIAN - Migrate xian superuser to proper user structure (1-2h)

Total: 12 issues, 20-29 hours estimated Actual Duration: 1-2 days (based on 88% velocity pattern from Sprint A6) Execution Order: See /dev/active/sprint-a7-gameplan-polish-buffer.md

Sprint A8: Alpha Prep & Launch ⏳ (Oct 27 - Nov 1)

Next Sprint - Final Alpha sprint before Wave 2 launch

Testing & Validation:

End-to-end workflow testing
Performance validation
Security audit

Documentation:

User guides and onboarding materials
Known issues documentation
Feature status documentation

Alpha Deployment:

Design onboarding communications
Invitation emails with instructions
Issue reporting guidelines
Testing checklists
A/B test design

Baseline Piper Education (demoted from Phase 3, 90% complete):

Self-knowledge (ethics ✅, spatial intelligence ✅)
Ethical values documentation
Spatial intelligence patterns
Growth mindset training
Systematic blindness awareness
Flywheel Methodology integration
Domain knowledge (PM, clients, projects)

Estimated Duration: 3-5 days Target: Alpha Wave 2 launch readiness

Alpha Milestone Completion Analysis

✅ Completed Sprints (6 of 8)

Sprint A1: Critical Infrastructure (5 issues)
Sprint A2: Notion & Errors (5 issues)
Sprint A3: Core Activation (4 issues)
Sprint A4: Standup Epic (4 issues)
Sprint A5: Learning System (7 issues)
Sprint A6: User Infrastructure (7 issues)

Total Delivered: 32 issues, 54 issues closed in Alpha milestone overall

🔜 Remaining Work (Sprints A7-A8)

Sprint A7: Polish & Buffer (12 issues, 20-29 hours):

CORE-UX: 4 issues
Critical fixes: 2 issues
CORE-KEYS: 3 issues
CORE-ALPHA: 3 issues

Sprint A8: Alpha Prep & Launch (activities, 3-5 days):

Testing & validation
Documentation
Alpha deployment prep
Baseline Piper Education completion

Total Remaining: 12 issues + A8 activities Estimated Completion: Early November 2025

Post-Alpha Path

Phase 3: Alpha Testing v0.1 (Early November 2025)

Status: Ready to begin after Sprint A8

Internal testing with development team (Alpha Wave 2)
Performance validation
Security audit
End-to-end workflow testing
User feedback integration
Decision Point: Assess MVP readiness

Phase 4: MVP Completion (Nov-Dec 2025)

What MVP Needs (from VALID-2 assessment):

Already Implemented (70-75% complete):

✅ Intent classification (98.62% accuracy)
✅ 22 production handlers including:
- GitHub operations (create, update, analyze)
- Summarization with LLM (145 lines)
- Strategic planning (125 lines)
- Pattern learning (94 lines)
✅ Plugin architecture (4 plugins operational)

Configuration Required (1 week):

🔧 GitHub API token
🔧 OpenAI/Anthropic API keys
🔧 Slack OAuth setup
🔧 Notion API credentials
🔧 Google Calendar credentials

Testing Required (1 week):

🔧 E2E with real APIs (not mocked)
🔧 User journey validation
🔧 Performance under load

Polish Required (1 week):

🔧 Greeting/help content
🔧 Error message refinement
🔧 User documentation

MVP Features to Validate: All originally planned features still need verification:

Chitchat (greeting, help/menu)
Knowledge (upload, summarize, analyze)
Lists (todo management)
Integrations (GitHub, Slack, Notion, Calendar)
Jobs (updates, standup generation)

Phase 5: Beta Testing v0.9 (December 2025)

Limited external users
Scale testing
Enterprise features

Phase 6: Launch v1.0 (January 2026)

Public availability
SLA commitment
Full documentation

Critical Insights from CRAFT

What Changed Our Understanding

Handlers aren’t placeholders - 22 production implementations exist
MVP closer than expected - 70-75% complete vs assumed 40%
Learning already started - Pattern learning handler exists
Standup partially done - Handler exists, needs wiring

What DOESN’T Change

Alpha plan execution - All A2-A7 items get verified
No skipping - Even if handlers exist, we verify everything
Quality standards - 100% completion required
Inchworm protocol - Sequential, methodical progress

Timeline Summary

October 2025: ✅ Mostly Complete

Week 2: Sprint A1 + CRAFT ✅
Week 3: Sprint A2 ✅
Week 4: Sprint A3-A6 ✅ (accelerated)
Oct 22-26: Sprint A7 ➡️ (12 issues, 1-2 days actual)
Oct 27 - Nov 1: Sprint A8 ⏳ (Alpha prep, 3-5 days)

Early November 2025:

Alpha Wave 2 launch
Phase 3: Alpha Testing with Wave 2 users
User feedback integration

Mid-Late November 2025:

MVP Configuration (API keys, OAuth)
Decision Point: MVP scope finalization
MVP Polish and Testing

December 2025:

Beta preparation
Beta testing (v0.9)

January 2026:

1.0 preparation
Public launch

Success Metrics

CORE Completion ✅ (October 22, 2025)

✅ All A1-A6 sprints complete (32 issues delivered)
✅ Every item verified (not assumed)
✅ Documentation current
✅ Tests comprehensive (250+ tests, 100% passing)
➡️ Sprint A7 in progress (12 issues, 1-2 days actual)
⏳ Sprint A8 planned (Alpha prep, 3-5 days)

Alpha Success Criteria (Early November 2025)

✅ Core functionality operational (all handlers working)
✅ Performance baselines maintained (602K req/sec)
✅ Multi-user support working (JWT, API keys, onboarding)
✅ Security hardened (SSL/TLS, audit trail, keychain)
🔜 UX polished (Sprint A7 - 12 issues)
🔜 API key lifecycle complete (CORE-KEYS)
🔜 User architecture separated (CORE-ALPHA)
🔜 Alpha prep complete (Sprint A8)
🔜 Alpha Wave 2 launched

MVP Launch (December 2025)

🔜 Configuration complete (API keys, OAuth)
🔜 E2E tests passing with real APIs
🔜 User journeys validated
🔜 Documentation ready for external users

Risk Management

Mitigated Risks ✅

Partial implementations (CRAFT verified completeness)
Technical debt (zero accumulation)
Regression (quality gates active)

Active Risks

Configuration availability (API keys needed)
OAuth complexity (Slack, Google)
Timeline pressure (resist shortcuts)

Mitigation Strategy

Follow Alpha plan exactly
Verify everything systematically
Document all discoveries
No skipping, no assumptions

Key Principle: Trust but Verify

CRAFT showed us that much more is implemented than we knew. This is fantastic! But we still:

Verify every Alpha checklist item
Test every integration point
Document every gap
Complete every sprint fully

The handlers existing means sprints might go faster, not that we skip verification.

This roadmap reflects the remarkable progress through Sprint A6, with Sprint A7 expanded to 12 issues and Sprint A8 added for Alpha prep. Quality and completeness continue to determine pace, not arbitrary deadlines.

Version: 10.0 Last Updated: October 22, 2025, 3:30 PM PDT Next Update: After Sprint A7 completion or Sprint A8 start Previous: v9.0 (Oct 22, 2025, 1:45 PM) - Sprint A6 Complete