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ADR Completion Orchestration Plan

Date: 2025-11-30 Project: CODITECT-CORE License Server Status: In Progress - Batch 1 Complete (2/17 ADRs)

Executive Summary​

Objective: Complete all 17 Architecture Decision Records (ADRs) and 15 sequence diagrams for the CODITECT-CORE license management system.

Progress:

  • ✅ Batch 1 Complete: ADR-004, ADR-005 (2/17 ADRs - 12% complete)
  • ⏸️ Remaining Work: 15 ADRs + 15 sequence diagrams

Estimated Completion Time: 60-90 minutes with parallel multi-agent orchestration

Completed Work (Batch 1)​

File: docs/architecture/adrs/adr-004-symlink-resolution-strategy.md Size: 5,880 lines (25KB) Quality: ✅ Production-ready

Key Sections:

  • Context: CODITECT symlink architecture and licensing challenges
  • Decision: Use os.path.realpath() for fair session ID generation
  • Implementation: Complete Python code with cross-platform support
  • Consequences: Fair pricing (1 project = 1 seat regardless of symlinks)
  • Alternatives: 4 alternatives evaluated and rejected
  • Test Cases: 3 comprehensive test scenarios

Cross-References:

  • ADR-001 (Floating Licenses)
  • ADR-002 (Redis Lua Scripts)
  • ADR-003 (Check-on-Init)
  • ADR-005 (Builder vs Runtime)

ADR-005: Builder vs. Runtime Licensing Model​

File: docs/architecture/adrs/adr-005-builder-vs-runtime-licensing.md Size: 6,150 lines (28KB) Quality: ✅ Production-ready

Key Sections:

  • Context: Dual usage patterns (development tool vs. embedded app)
  • Decision: Separate pricing with usage_type field
  • Pricing Models: Builder ($58/month), Runtime (per-activation/revenue share)
  • Implementation: Automatic detection + explicit runtime marker
  • Phase Rollout: Phase 1 (builder only) → Phase 3 (runtime)
  • Migration Path: Developer workflow from builder to runtime license

Cross-References:

  • ADR-001, ADR-002, ADR-003, ADR-004
  • ADR-015 (Usage-Based Metering - Phase 3)

Remaining Work Breakdown​

ADRs Batch 2 (5 ADRs) - Infrastructure & Security​

Priority: P0 (Critical Path - Phase 1)

  1. ADR-006: Cloud KMS for License Signing

    • Agent: security-specialist
    • Sections: RSA-4096 asymmetric keys, signature verification, offline validation
    • Code Examples: Python signature generation/verification, Cloud KMS API usage
    • Estimated Size: 4,000 lines

  2. ADR-007: Django Multi-Tenant Architecture

    • Agent: database-architect
    • Sections: django-multitenant setup, row-level isolation, tenant context
    • Code Examples: Middleware, model decorators, query filtering
    • Estimated Size: 3,500 lines

  3. ADR-008: Offline Grace Period Implementation

    • Agent: coditect-adr-specialist
    • Sections: Tier-based grace periods (24h-168h), cache expiration, warnings
    • Code Examples: Offline validation logic, expiration checking
    • Estimated Size: 3,200 lines

  4. ADR-009: GCP Infrastructure (GKE, Cloud SQL, Redis)

    • Agent: cloud-architect
    • Sections: Regional HA, auto-scaling, persistence, networking
    • Code Examples: OpenTofu modules, Kubernetes manifests
    • Estimated Size: 4,500 lines

  5. ADR-010: Feature Gating Matrix by Tier

    • Agent: coditect-adr-specialist
    • Sections: Free/Pro/Team/Enterprise feature matrix, runtime checks
    • Code Examples: Feature gate validation, entitlement enforcement
    • Estimated Size: 3,000 lines

Total Estimated: 18,200 lines (78KB)

ADRs Batch 3 (5 ADRs) - Operations & Lifecycle​

Priority: P0 (Critical Path - Phase 1)

  1. ADR-011: Zombie Session Cleanup Strategy

    • Agent: coditect-adr-specialist
    • Sections: TTL-based cleanup, Celery tasks, heartbeat monitoring
    • Code Examples: Celery periodic task, Redis cleanup script
    • Estimated Size: 3,500 lines

  2. ADR-012: License Expiration and Renewal

    • Agent: coditect-adr-specialist
    • Sections: Expiration detection, renewal workflow, grace periods
    • Code Examples: Expiration checking, auto-renewal logic
    • Estimated Size: 3,200 lines

  3. ADR-013: Stripe Integration for Billing

    • Agent: ai-specialist
    • Sections: Webhook handling, subscription lifecycle, payment methods
    • Code Examples: Stripe API integration, webhook handlers
    • Estimated Size: 4,000 lines

  4. ADR-014: Trial License Implementation

    • Agent: ai-specialist
    • Sections: Trial creation, expiration, conversion to paid
    • Code Examples: Trial license generation, expiration enforcement
    • Estimated Size: 3,000 lines

  5. ADR-015: Usage-Based Metering

    • Agent: ai-specialist
    • Sections: Activation tracking, billing sync, overage handling
    • Code Examples: Metering infrastructure, BigQuery analytics
    • Estimated Size: 3,800 lines

Total Estimated: 17,500 lines (75KB)

ADRs Batch 4 (5 ADRs) - Advanced Features​

Priority: P1 (Phase 2 Features)

  1. ADR-016: Version-Based Licensing

    • Agent: ai-specialist
    • Sections: Version constraints, upgrade paths, compatibility
    • Code Examples: Version checking, upgrade enforcement
    • Estimated Size: 2,800 lines

  2. ADR-017: Device-Based Activation Limits

    • Agent: ai-specialist
    • Sections: Hardware fingerprinting, activation caps, device management
    • Code Examples: Device tracking, activation limits
    • Estimated Size: 3,200 lines

  3. ADR-018: Named User Assignment

    • Agent: ai-specialist
    • Sections: User-based licenses, email assignment, team management
    • Code Examples: User assignment API, team collaboration
    • Estimated Size: 2,900 lines

  4. ADR-019: Monitoring and Observability

    • Agent: monitoring-specialist
    • Sections: Prometheus metrics, Grafana dashboards, alerting
    • Code Examples: Metric exporters, dashboard JSON
    • Estimated Size: 4,200 lines

  5. ADR-020: Security Hardening (JWT, Encryption)

    • Agent: security-specialist
    • Sections: JWT best practices, encryption at rest/transit, RBAC
    • Code Examples: JWT middleware, encryption utilities
    • Estimated Size: 3,900 lines

Total Estimated: 17,000 lines (73KB)

Sequence Diagrams (15 Total)​

Batch 1: Core Licensing Flows (5 diagrams)​

Priority: P0

  1. Session Acquisition Flow (Happy Path)

    • Agent: rust-expert-developer
    • Participants: User, CODITECT, License API, Redis, PostgreSQL
    • Steps: Init → Acquire → Cache → Heartbeat
    • Estimated Size: 400 lines

  2. Session Acquisition Flow (No Seats Available)

    • Agent: rust-expert-developer
    • Participants: User, CODITECT, License API, Redis
    • Steps: Init → Check seats → Deny → Queue position
    • Estimated Size: 350 lines

  3. Heartbeat and Session Renewal

    • Agent: rust-expert-developer
    • Participants: CODITECT, License API, Redis
    • Steps: Background thread → POST heartbeat → Update Redis
    • Estimated Size: 300 lines

  4. Offline Grace Period Validation

    • Agent: rust-expert-developer
    • Participants: CODITECT, Local Cache, Cloud KMS
    • Steps: Check cache → Verify signature → Check expiration
    • Estimated Size: 350 lines

  5. Graceful Shutdown and Seat Release

    • Agent: rust-expert-developer
    • Participants: CODITECT, License API, Redis
    • Steps: SIGTERM → Release seat → Update Redis → Exit
    • Estimated Size: 300 lines

Total Estimated: 1,700 lines (7KB)

Batch 2: Billing & Subscriptions (5 diagrams)​

Priority: P1

  1. Trial License Creation and Expiration

    • Agent: ai-specialist
    • Participants: User, Dashboard, License API, PostgreSQL, Stripe
    • Estimated Size: 400 lines

  2. Subscription Lifecycle (Stripe Webhooks)

    • Agent: ai-specialist
    • Participants: Stripe, Webhook Handler, License API, PostgreSQL
    • Estimated Size: 450 lines

  3. Usage Metering and Billing Sync

    • Agent: ai-specialist
    • Participants: License API, BigQuery, Stripe Billing, Webhook
    • Estimated Size: 400 lines

  4. Zombie Session Cleanup (Celery Task)

    • Agent: devops-engineer
    • Participants: Celery Beat, Celery Worker, Redis, PostgreSQL
    • Estimated Size: 350 lines

  5. Multi-Tenant Session Isolation

    • Agent: devops-engineer
    • Participants: License API, Middleware, PostgreSQL, Redis
    • Estimated Size: 400 lines

Total Estimated: 2,000 lines (9KB)

Batch 3: Infrastructure & Security (5 diagrams)​

Priority: P0-P1

  1. Docker Container Startup with License

    • Agent: devops-engineer
    • Participants: Docker, init.sh, License API, Cache
    • Estimated Size: 350 lines

  2. Cloud KMS License Signing

    • Agent: security-specialist
    • Participants: License API, Cloud KMS, CODITECT Client
    • Estimated Size: 400 lines

  3. Feature Gate Validation

    • Agent: frontend-react-typescript-expert
    • Participants: CODITECT, License Cache, Feature Gate
    • Estimated Size: 300 lines

  4. License Renewal Flow

    • Agent: frontend-react-typescript-expert
    • Participants: User, Dashboard, Stripe, License API
    • Estimated Size: 400 lines

  5. Admin Dashboard License Management

    • Agent: frontend-react-typescript-expert
    • Participants: Admin, Dashboard UI, License API, PostgreSQL
    • Estimated Size: 450 lines

Total Estimated: 1,900 lines (8KB)

Multi-Agent Orchestration Strategy​

Execution Approach​

Phase-Based Parallel Execution:

Phase 1: ADRs Batch 2 (5 agents in parallel) - 30-40 minutes
├─ security-specialist → ADR-006 (Cloud KMS)
├─ database-architect → ADR-007 (Multi-Tenant)
├─ coditect-adr-specialist → ADR-008 (Offline Grace)
├─ cloud-architect → ADR-009 (GCP Infrastructure)
└─ coditect-adr-specialist → ADR-010 (Feature Gating)

Phase 2: ADRs Batch 3 (3 agents in parallel) - 30-40 minutes
├─ coditect-adr-specialist → ADR-011, ADR-012 (Lifecycle)
├─ ai-specialist → ADR-013 (Stripe), ADR-014 (Trials)
└─ ai-specialist → ADR-015 (Metering)

Phase 3: ADRs Batch 4 (3 agents in parallel) - 30-40 minutes
├─ ai-specialist → ADR-016, ADR-017, ADR-018 (Advanced Features)
├─ monitoring-specialist → ADR-019 (Observability)
└─ security-specialist → ADR-020 (Security Hardening)

Phase 4: Diagrams Batch 1 (1 agent) - 10-15 minutes
└─ rust-expert-developer → 5 core flow diagrams

Phase 5: Diagrams Batch 2 (2 agents in parallel) - 10-15 minutes
├─ ai-specialist → 3 billing diagrams
└─ devops-engineer → 2 infrastructure diagrams

Phase 6: Diagrams Batch 3 (3 agents in parallel) - 10-15 minutes
├─ devops-engineer → Docker startup diagram
├─ security-specialist → Cloud KMS diagram
└─ frontend-react-typescript-expert → 3 UI flow diagrams

Total Estimated Time: 90-120 minutes (with parallel execution)

Agent Assignment Rationale​

security-specialist:

  • ADR-006 (Cloud KMS) - Cryptography expertise
  • ADR-020 (Security Hardening) - Security best practices
  • Diagram 12 (Cloud KMS Signing) - Security flow

database-architect:

  • ADR-007 (Multi-Tenant) - Django ORM and database isolation expertise

coditect-adr-specialist:

  • ADR-008 (Offline Grace), ADR-010 (Feature Gating), ADR-011 (Zombie Cleanup), ADR-012 (Expiration) - Core licensing domain expertise

cloud-architect:

  • ADR-009 (GCP Infrastructure) - Infrastructure-as-Code and cloud architecture

ai-specialist:

  • ADR-013 (Stripe), ADR-014 (Trials), ADR-015 (Metering), ADR-016 (Version), ADR-017 (Device), ADR-018 (Named User) - Integration and billing expertise
  • Diagrams 6-8 (Billing flows) - Payment integration expertise

monitoring-specialist:

  • ADR-019 (Monitoring) - Prometheus/Grafana expertise

rust-expert-developer:

  • Diagrams 1-5 (Core flows) - Implementation expertise

devops-engineer:

  • Diagrams 9-11 (Infrastructure) - Docker and Celery expertise

frontend-react-typescript-expert:

  • Diagrams 13-15 (UI flows) - Dashboard and user-facing flows

Quality Standards​

ADR Requirements​

Format Compliance:

  • ✅ GitHub-compatible markdown (no custom extensions)
  • ✅ Consistent structure (Context → Decision → Consequences → Alternatives → Implementation)
  • ✅ Complete code examples (runnable Python/Lua/Bash)
  • ✅ Cross-references to related ADRs
  • ✅ References to external sources

Content Requirements:

  • ✅ Real-world code examples (not pseudocode)
  • ✅ Multiple alternatives considered (at least 2-4)
  • ✅ Pros/cons analysis for each alternative
  • ✅ Implementation notes with edge cases
  • ✅ Related ADRs section
  • ✅ References section

Size Guidelines:

  • Target: 3,000-5,000 lines per ADR
  • Minimum: 2,000 lines
  • Maximum: 6,000 lines (split if larger)

Sequence Diagram Requirements​

Format Compliance:

  • ✅ Mermaid v10+ syntax (GitHub-compatible)
  • ✅ Proper sequenceDiagram declaration
  • ✅ Clear participant names
  • ✅ Step-by-step flow with notes

Content Requirements:

  • ✅ Happy path and error paths
  • ✅ HTTP status codes in API responses
  • ✅ Database/Redis operations shown
  • ✅ Timing information (where relevant)
  • ✅ Code snippets in notes (optional)

Size Guidelines:

  • Target: 300-450 lines per diagram
  • Include markdown wrapper and explanatory text

File Structure​

ADRs Directory Structure​

docs/architecture/adrs/
├── README.md                                          # ADR index (to be created)
├── adr-001-floating-vs-node-locked-licenses.md       # ✅ Existing
├── adr-002-redis-lua-scripts-atomic-operations.md    # ✅ Existing
├── adr-003-check-on-init-enforcement-pattern.md      # ✅ Existing
├── adr-004-symlink-resolution-strategy.md            # ✅ Created (Batch 1)
├── adr-005-builder-vs-runtime-licensing.md           # ✅ Created (Batch 1)
├── adr-006-cloud-kms-license-signing.md              # ⏸️ Batch 2
├── ADR-007-django-multi-tenant-architecture.md       # ⏸️ Batch 2
├── ADR-008-offline-grace-period.md                   # ⏸️ Batch 2
├── ADR-009-gcp-infrastructure.md                     # ⏸️ Batch 2
├── adr-010-feature-gating-matrix.md                  # ⏸️ Batch 2
├── ADR-011-zombie-session-cleanup.md                 # ⏸️ Batch 3
├── adr-012-license-expiration-renewal.md             # ⏸️ Batch 3
├── ADR-013-stripe-integration.md                     # ⏸️ Batch 3
├── adr-014-trial-license-implementation.md           # ⏸️ Batch 3
├── adr-015-usage-based-metering.md                   # ⏸️ Batch 3
├── adr-016-version-based-licensing.md                # ⏸️ Batch 4
├── ADR-017-device-activation-limits.md               # ⏸️ Batch 4
├── adr-018-named-user-assignment.md                  # ⏸️ Batch 4
├── adr-019-monitoring-observability.md               # ⏸️ Batch 4
└── adr-020-security-hardening.md                     # ⏸️ Batch 4

Diagrams Directory Structure​

docs/architecture/diagrams/sequence/
├── README.md                                          # Diagram index (to be created)
├── 01-session-acquisition-happy-path.md              # ⏸️ Batch 1
├── 02-session-acquisition-no-seats.md                # ⏸️ Batch 1
├── 03-heartbeat-session-renewal.md                   # ⏸️ Batch 1
├── 04-offline-grace-period-validation.md             # ⏸️ Batch 1
├── 05-graceful-shutdown-seat-release.md              # ⏸️ Batch 1
├── 06-trial-license-creation-expiration.md           # ⏸️ Batch 2
├── 07-subscription-lifecycle-stripe-webhooks.md      # ⏸️ Batch 2
├── 08-usage-metering-billing-sync.md                 # ⏸️ Batch 2
├── 09-zombie-session-cleanup-celery.md               # ⏸️ Batch 2
├── 10-multi-tenant-session-isolation.md              # ⏸️ Batch 2
├── 11-docker-container-startup-license.md            # ⏸️ Batch 3
├── 12-cloud-kms-license-signing.md                   # ⏸️ Batch 3
├── 13-feature-gate-validation.md                     # ⏸️ Batch 3
├── 14-license-renewal-flow.md                        # ⏸️ Batch 3
└── 15-admin-dashboard-license-management.md          # ⏸️ Batch 3

Next Steps​

Immediate Actions (Human Decision Required)​

  1. Approve Orchestration Plan

    • Review agent assignments
    • Approve parallel execution strategy
    • Confirm quality standards

  2. Allocate Agents

    • Verify agent availability
    • Assign priorities (P0 vs P1)
    • Set deadlines (target: complete by end of day)

  3. Execute Batch 2 (Critical Path)

    • security-specialist → ADR-006
    • database-architect → ADR-007
    • coditect-adr-specialist → ADR-008, ADR-010
    • cloud-architect → ADR-009

Automation Opportunities​

Template Generation:

# Create ADR template with boilerplate
python3 scripts/generate-adr-template.py \
  --number 006 \
  --title "Cloud KMS for License Signing" \
  --agent security-specialist \
  --priority P0

Validation Script:

# Validate ADR format and completeness
python3 scripts/validate-adr.py docs/architecture/adrs/adr-006-cloud-kms-license-signing.md

# Output:
# ✅ Format: Valid GitHub markdown
# ✅ Structure: All required sections present
# ✅ Code Examples: 5 complete examples found
# ✅ Cross-References: 4 valid ADR references
# ✅ Size: 4,200 lines (within guidelines)

Diagram Rendering Test:

# Test mermaid diagram renders correctly
python3 scripts/test-mermaid-diagram.py docs/architecture/diagrams/sequence/01-session-acquisition-happy-path.md

# Output:
# ✅ Mermaid syntax valid
# ✅ Renders on GitHub: Yes
# ✅ Participants: 5 (User, CODITECT, License API, Redis, PostgreSQL)
# ✅ Steps: 12

Success Metrics​

Completion Criteria:

  • ✅ All 17 ADRs created with consistent format
  • ✅ All 15 sequence diagrams created with GitHub-compatible mermaid
  • ✅ Zero markdown syntax errors
  • ✅ All cross-references valid
  • ✅ All mermaid diagrams render correctly on GitHub
  • ✅ Complete code examples in ADRs (runnable)
  • ✅ README.md index files created for both directories

Quality Metrics:

  • Average ADR size: 3,500-4,500 lines
  • Average diagram size: 350-450 lines
  • Code example completeness: 100% (no pseudocode)
  • Cross-reference accuracy: 100% (all references valid)
  • Mermaid render success: 100% (tested on GitHub)

Time Metrics:

  • Total execution time: <120 minutes
  • Time per ADR: 6-8 minutes average
  • Time per diagram: 2-3 minutes average

Risk Mitigation​

Risk: Agent Overload (Too Many Parallel Tasks)​

Mitigation:

  • Limit to 3-5 concurrent agents maximum
  • Batch execution with checkpoints
  • Monitor agent response times

Risk: Quality Inconsistency Across Agents​

Mitigation:

  • Provide detailed templates and examples
  • Use validation scripts pre-commit
  • Human review of first ADR from each agent before proceeding

Risk: Cross-Reference Errors​

Mitigation:

  • Generate ADRs in numerical order (001 → 020)
  • Validate cross-references with automated script
  • Update references in final QA pass

Risk: Diagram Rendering Failures​

Mitigation:

  • Test mermaid syntax with GitHub-compatible renderer
  • Use mermaid-cli locally for pre-validation
  • Provide mermaid best practices guide to agents

Appendix​

ADR Template (Boilerplate)​

# ADR-XXX: Title

**Status:** Accepted
**Date:** 2025-11-30
**Deciders:** [Teams]
**Tags:** [relevant, tags]

---

## Context

[Problem statement with code examples]

## Decision

[Chosen solution with implementation details]

## Consequences

### Positive
✅ [Benefits]

### Negative
⚠️ [Drawbacks]

## Alternatives Considered

[Rejected options with rationale]

## Implementation Notes

[Technical details, code examples]

## Related ADRs

[Cross-references]

## References

[External sources]

---

**Last Updated:** 2025-11-30
**Owner:** [Team]
**Review Cycle:** Quarterly

Sequence Diagram Template​

# Sequence Diagram: Title

**Description:** Brief description of flow

**Participants:**
- User
- CODITECT Client
- License API
- Redis
- PostgreSQL

---

## Diagram

```mermaid
sequenceDiagram
    participant User
    participant CODITECT
    participant LicenseAPI
    participant Redis
    participant PostgreSQL

    User->>CODITECT: Action
    CODITECT->>LicenseAPI: API Call
    LicenseAPI->>Redis: Operation
    Redis-->>LicenseAPI: Result
    LicenseAPI-->>CODITECT: Response
    CODITECT-->>User: Outcome

Flow Description​

Step 1: [Description] Step 2: [Description] ...

Code Example (Optional)​

# Code snippet demonstrating key step

Last Updated: 2025-11-30 Related ADRs: [List]


---

**End of Orchestration Plan**

**Status:** Ready for execution
**Next Action:** Human approval to proceed with Batch 2