Piper Morgan Roadmap v15.0

Date: April 11, 2026 Author: PA, with leadership review (PPM, CXO, CIO, Architect) Status: Active. M1 closed April 11. M2 begins now. Supersedes: v14.3 (March 10, 2026) — archived at docs/internal/planning/historical/roadmap-v14.3-2026-03-10.md


Executive Summary

M1 (MVP Foundation) closed April 11, 2026 at 7/9 Gate 1 PASS after four UAT rounds. The closure follows a major strategic pivot: M2-M5 has been restructured around the differentiator stack (context methodology + conscious floor + artifact persistence + trust-graduated experience) per Vision V2.3. The previous sprint themes (Activation, Skills, Documents, Polish) are retired in favor of themes that map directly to what makes Piper Piper.

Key changes from v14.3:


Current Position

Inchworm Position: 4.4.3 (M1 closed, M2 starting)

1. ✅ The Great Refactor (GREAT)
2. ✅ CORE functionality
3. ✅ ALPHA testing (v0.8.0 → v0.8.5.1)
4. 🎯 Complete build of MVP
   4.1. ✅ B1 - Beta Enablers (v0.8.3.x) - COMPLETE Jan 11
   4.2. ✅ A20 - Alpha Testing round 2 (v0.8.4.x) - COMPLETE Jan 18
   4.3. ✅ MUX: Modeled User Experience - COMPLETE Jan 27
   4.4. 🎯 MVP Sprints (M0 → M5) ← CURRENT
        ✅ M0: Conversational Glue — COMPLETE (v0.8.6, Mar 4)
        ✅ M1: Foundation — COMPLETE (gate closed Apr 11, 7/9 Gate 1 PASS)
        🎯 M2: Conscious Floor + Action Handlers ← STARTING
        ○ M3: Artifact Persistence
        ○ M4: Trust + Learning
        ○ M5: Distribution + Polish
5. Beta testing on 0.9
6. Launch 1.0

The Differentiator Stack (Vision V2.3)

The MVP sprints are organized around four differentiators that, together, make Piper a colleague rather than a chatbot wrapper:

  1. Context Methodology — Five-layer model operationalized as practiced discipline
  2. Conscious Floor — LLM responses embodying grammar, Five Pillars, anti-flattening
  3. Artifact Persistence — Conversation outputs that outlive the conversation, with composting lifecycle
  4. Trust-Graduated Experience — Earned proactivity through demonstrated value

Indoor plumbing (commodity, not differentiating): GitHub/Slack/Calendar/Notion via MCP plugins, file storage via SQLite, auth via standard OAuth, LLM provider management via adapter pattern.


MVP Sprint Status (April 11, 2026)

M0 — Conversational Glue ✅ COMPLETE

Status: COMPLETE — v0.8.6 shipped March 4, 2026 Theme: Natural conversation flow Final Totals: 27 issues (5 planned + 22 discovered via Assembly Assumption)


M1 — MVP Foundation ✅ COMPLETE

Status: COMPLETE — Gate #926 closed April 11, 2026 Theme: Floor-first routing + security + testing foundation Final Result: Gate 1 7/9 PASS (Q2 marginal, Q8 #922 conversation continuity deferred to M2) Test Suite: 6,309 passing, 0 failures

Key shipped:

Lessons learned (for M2 planning):


M2 — Conscious Floor + Action Handlers 🎯 CURRENT

Theme: Make the conscious floor reliable and the action gate clean. The differentiator stack’s first two pillars become operational. Status: Starting April 11

Sprint focus: Floor reliability, context assembly across all floor-routed categories, action gate routing for the few side-effect handlers, E2E + AAXT testing infrastructure.

Issues:

# Title Type
#557 ARCH: WebSocket Infrastructure for Real-Time Communication Architecture
#542 SEC: Implement actual token revocation on disconnect Security
#482 SEC-KMS-INTEGRATION: Migrate from environment variable to AWS KMS Security
#472 EPIC: Slack Integration TDD Gaps - OAuth and Spatial Methods Integration
#470 EPIC: SEC-RBAC Phases 4-5 - Projects and Files Ownership Security
#790 MVP: Trust-gated calendar integration behavior Integration
#100 CONV-FEAT-PROJ: Project Portfolio Awareness (revised → context shape) Context
#101 CONV-FEAT-TIME: Temporal Context System (revised → context shape) Context
#304 CONV-INFR-NOTN: Activate Existing Notion Integration Integration
#366 SLACK-MEMORY: Persist spatial patterns over time Integration
#371 INFRA-TIMESERIES: Implement Time-Series Database Infrastructure Infrastructure
#471 EPIC: Infrastructure - OAuth, Learning, TimeSeries, Conversation Infrastructure
#683 MUX-WIRE-DOD: Update DoD to require interface verification Process
#690 WIRE-BOUNDARY: Wire BoundaryEnforcer in LLM classifier factory Wiring
#691 WIRE-CANONICAL: Replace in-memory repository with database-backed Wiring
#692 WIRE-SLACK: Integrate blocker detection in Slack webhook router Wiring
#693 WIRE-STANDUP: Fetch standup workflow settings from user configuration Wiring
#694 WIRE-GITHUB-LLM: Replace placeholder with actual LLM call in issue generator Wiring
#695 WIRE-GITHUB-CMD: Integrate GitHub issue command with actual GitHub service Wiring
#703 MUX-LIFECYCLE-UI: Lifecycle indicator integration (revise: implementation-agnostic) Experience
#707 MUX-INSIGHT-SURFACING: Implement Insight Surfacing Rules Experience
#714 MUX-LISTS-LIFECYCLE-UI: Wire Lifecycle/Staleness to Lists View (revise) Experience
#869 Project configuration IA: Project Detail as primary UX
#925 Floor inversion Phase 3-4: STATUS/PRIORITY floor-first Floor
#927 E2E: Task lifecycle smoke tests through /api/v1/intent Testing
#928 E2E: Automated canonical conversation suite Testing
#929 AAXT: Golden scenarios with DeepEval LLM-as-judge Testing
#930 CI: Integration for E2E conversations + AAXT nightly Testing
#946 LLM system uses stale keychain keys without user consent Bug
#947 Dual LLM systems (LLMClient vs LLMDomainService) cause hidden config drift Tech Debt
#950 FLOOR-PROMPT: Conscious floor system prompt with Five Pillars + grammar NEW
#951 CONTEXT-ASSEMBLER-EXPAND: Context assembly for all floor-routed categories NEW
#960 Floor fabrication root fix NEW (from M1 testing)
#961 Floor-route context audit NEW (from M1 testing)
#962 LLM-shortcut inversion sweep NEW (from M1 testing)

Pre-sprint actions (per leadership review):

Sprint expansion expectation: M0 expanded 5→27 issues (5.4x), M1 expanded ~2x. The context assembler is the kind of work that reveals gaps. Plan for 6-8 weeks rather than 4.


M3 — Artifact Persistence

Theme: Conversation outputs that outlive the conversation. The bridge between “good conversation” and “useful PM tool.” Status: Pending M2 closure

Issues:

# Title Type
#864 INTENT-COVERAGE: Pre-classifier patterns for milestones, labels, releases, branches Coverage
#118 INFR-AGENT: Multi-Agent Coordinator Operational Deployment Architecture
#313 CONV-UX-DOCS: File Browser & Document Management UI (revise: implementation-agnostic) Experience
#355 DOCS-STOPGAP: Basic Artifact Persistence (centerpiece) Persistence
#496 CANONICAL-#9: Enhance priority queries with real priority data (context shape) Context
#497 CANONICAL-#10: Enhance focus guidance with calendar + projects + priorities synthesis Context
#669 COMPOSTING-HYBRID-TRIGGER: Add time-based forcing Lifecycle
#704 MUX-LIFECYCLE-UI-A: Morning Standup lifecycle indicator (revise) Experience
#716 MUX-FEATURES-VIEW: Create Features View with Lifecycle Experience
#952 ARTIFACT-MODEL: Artifact data model with lifecycle states NEW
#953 CONTEXT-PERSIST: Cross-session memory persistence (Layer 4 gap fix) NEW

Pre-sprint actions:


M4 — Trust + Learning

Theme: Earned proactivity and cumulative understanding. The differentiator stack’s third and fourth pillars. Status: Pending M3 closure

Issues:

# Title Type
#558 MUX-STANDUP-CONVERSE: LLM-based preference extraction Learning
#302 CONV-MCP-DOCS: Unified Document Processing (revised — strip Skills framing) Documents
#712 MUX-DOCUMENT-VIEWER: Create Document Viewer with Lifecycle (revise) Experience
#713 MUX-DOCUMENTS-LIFECYCLE-UI: Wire Lifecycle to Documents View (revise) Experience
#954 TRUST-LITE: Trust graduation via context (lightweight implementation) NEW
#955 PREF-INFER: User-correctable preferences (Claude memory model) NEW
#956 LEARNING-SURFACE: Trust-graduated learning surfacing NEW

Pre-sprint actions:


M5 — Distribution + Polish

Theme: Get Piper into users’ hands via Bring Your Own Chat. Distribution earlier rather than after polish. Status: Pending M4 closure

Issues:

# Title Type
#441 CORE-UX-AUTH-PHASE2: Registration, Password Reset, Security Polish Auth
#829 DIST-MCP-PACKAGE: Package Piper as MCP server Distribution
#830 DIST-MCP-DOCS: Integration documentation for MCP clients Distribution
#831 DIST-MCP-REGISTRY: Publish to package registries Distribution
#832 DIST-MCP-TEST: Integration testing with MCP clients Distribution
#857 INFRA: Token refresh mechanism for seamless session continuity Infrastructure
#865 REFACTOR: Extract setup wizard into component-based steps Tech Debt
#900 ENHANCE: Standup 3-part structural collection and enhanced completion Enhancement
#921 UPGRADE: FastAPI/Starlette/httpx to current versions Infrastructure
#932 SEC: HIBP integration stub — key leak detection Security
#933 SEC: API key validation disabled for alpha — re-enable plan Security
#935 TECH-DEBT: BudgetManager + APIUsageTracker have zero database persistence Tech Debt
#936 TECH-DEBT: UserService stores all user data in in-memory dicts Tech Debt
#948 Server leaves orphaned processes after stop Bug
#949 DEV: Server restart reliability — stale .pyc, orphaned processes Bug
#957 DIST-MCPB-BUNDLE: MCPB packaging for Claude Desktop one-click install NEW
#958 DIST-PROJECT-TEMPLATE: Claude Project template for Piper persona NEW
#959 DIST-MCP-APPS: Artifact canvas via MCP Apps (in-chat UI) NEW

Pre-sprint actions:


Closures and Revisions (Per Backlog Deep Review, April 7)

Closed (12 issues, all superseded by intervening work)

Revised (3 issues, scope updated)

Deferred to Horizon 2


Distribution Strategy: Bring Your Own Chat

Build sequence (Gall’s Law):

  1. MCP server — standalone, runs via stdio transport, exposes Piper tools (Python recommended per Architect for codebase reuse)
  2. MCPB packaging — bundle for Claude Desktop one-click install
  3. Claude Project template — persona/instructions for the hybrid approach (resolves system prompt injection gap)
  4. MCP Apps — interactive HTML for artifact canvas, only after tools work well in conversation

Cross-platform readiness: The MCP server is the product. MCPB is the first packaging for Claude Desktop. The same server works with any MCP-compatible client (ChatGPT, Gemini, VS Code, Goose). Persona adapts per platform.

Build the server cleanly enough that the packaging layer is swappable — anchor on the thin-wrapper-to-API model, not on MCP specifically.


Methodology Maintenance (Per CIO Observation)

Methodology-as-product is an asset only while it’s a living practice. The mechanisms that keep it alive:

These don’t appear in the feature roadmap but are required for the differentiator stack to remain credible.


Sprint Summary

Sprint Theme Status
M0 Conversational Glue ✅ COMPLETE (v0.8.6, Mar 4)
M1 MVP Foundation ✅ COMPLETE (gate closed Apr 11)
M2 Conscious Floor + Action Handlers 🎯 STARTING
M3 Artifact Persistence
M4 Trust + Learning
M5 Distribution + Polish

Timeline (Inchworm, Not Calendar)

These are sequence statements, not deadlines. We are time lords. Each phase complete before the next begins.

April 2026

Estimated forward sequence


Change Log