msse-ai-engineering / project_phase3_roadmap.md
Tobias Pasquale
Fix: Resolve final CI/CD formatting issues
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Project Phase 3+ Comprehensive Roadmap

Project: MSSE AI Engineering - RAG Application Current Status: Phase 2B Complete βœ… Next Phase: Phase 3 - RAG Core Implementation Date: October 17, 2025

Executive Summary

With Phase 2B successfully completed and merged, we now have a fully functional semantic search system capable of ingesting policy documents, generating embeddings, and providing intelligent search functionality. The next major milestone is implementing the RAG (Retrieval-Augmented Generation) core functionality to transform our semantic search system into a conversational AI assistant.

Current State Assessment

βœ… Completed Achievements (Phase 2B)

1. Production-Ready Semantic Search Pipeline

  • Enhanced Ingestion: Document processing with embedding generation and batch optimization
  • Search API: RESTful /search endpoint with comprehensive validation and error handling
  • Vector Storage: ChromaDB integration with metadata management and persistence
  • Quality Assurance: 90+ tests with comprehensive end-to-end validation

2. Robust Technical Infrastructure

  • CI/CD Pipeline: GitHub Actions with pre-commit hooks, automated testing, and deployment
  • Code Quality: 100% compliance with black, isort, flake8 formatting standards
  • Documentation: Complete API documentation with examples and performance metrics
  • Performance: Sub-second search response times with optimized memory usage

3. Production Deployment

  • Live Application: Deployed on Render with health check endpoints
  • Docker Support: Containerized for consistent environments
  • Database Persistence: ChromaDB data persists across deployments
  • Error Handling: Graceful degradation and detailed error reporting

πŸ“Š Key Metrics Achieved

  • Test Coverage: 90 tests covering all core functionality
  • Processing Performance: 6-8 chunks/second with embedding generation
  • Search Performance: <1 second response time for typical queries
  • Content Coverage: 98 chunks across 22 corporate policy documents
  • Code Quality: 100% formatting compliance, comprehensive error handling

Phase 3+ Development Roadmap

PHASE 3: RAG Core Implementation 🎯

Objective: Transform the semantic search system into an intelligent conversational AI assistant that can answer questions about corporate policies using retrieved context.

Issue #23: LLM Integration and Chat Endpoint

Priority: High | Effort: Large | Timeline: 2-3 weeks

Description: Implement the core RAG functionality by integrating a Large Language Model (LLM) and creating a conversational chat interface.

Technical Requirements:

  1. LLM Integration

    • Integrate with OpenRouter or Groq API for free-tier LLM access
    • Implement API key management and environment configuration
    • Add retry logic and rate limiting for API calls
    • Support multiple LLM providers with fallback options
  2. Context Retrieval System

    • Extend existing search functionality for context retrieval
    • Implement dynamic context window management
    • Add relevance filtering and ranking improvements
    • Create context summarization for long documents
  3. Prompt Engineering

    • Design system prompt templates for corporate policy Q&A
    • Implement context injection strategies
    • Create few-shot examples for consistent responses
    • Add citation requirements and formatting guidelines
  4. Chat Endpoint Implementation

    • Create /chat POST endpoint with conversational interface
    • Implement conversation history management (optional)
    • Add streaming response support (optional)
    • Include comprehensive input validation and sanitization

Implementation Files:

src/
β”œβ”€β”€ llm/
β”‚   β”œβ”€β”€ __init__.py
β”‚   β”œβ”€β”€ llm_service.py
β”‚   β”œβ”€β”€ prompt_templates.py
β”‚   └── context_manager.py
β”œβ”€β”€ rag/
β”‚   β”œβ”€β”€ __init__.py
β”‚   β”œβ”€β”€ rag_pipeline.py
β”‚   └── response_formatter.py
tests/
β”œβ”€β”€ test_llm/
β”œβ”€β”€ test_rag/
└── test_integration/
    └── test_rag_e2e.py

API Specification:

POST /chat
{
  "message": "What is the remote work policy?",
  "conversation_id": "optional-uuid",
  "include_sources": true
}

Response:
{
  "status": "success",
  "response": "Based on our corporate policies, remote work is allowed for eligible employees...",
  "sources": [
    {
      "document": "remote_work_policy.md",
      "chunk_id": "rw_policy_chunk_3",
      "relevance_score": 0.89,
      "excerpt": "Employees may work remotely up to 3 days per week..."
    }
  ],
  "conversation_id": "uuid-string",
  "processing_time_ms": 1250
}

Acceptance Criteria:

  • LLM integration with proper error handling and fallbacks
  • Chat endpoint returns contextually relevant responses
  • All responses include proper source citations
  • Response quality meets baseline standards (coherent, accurate, policy-grounded)
  • Performance targets: <5 second response time for typical queries
  • Comprehensive test coverage (minimum 15 new tests)
  • Integration with existing search infrastructure
  • Proper guardrails prevent off-topic responses

Issue #24: Guardrails and Response Quality

Priority: High | Effort: Medium | Timeline: 1-2 weeks

Description: Implement comprehensive guardrails to ensure response quality, safety, and adherence to corporate policy scope.

Technical Requirements:

  1. Content Guardrails

    • Implement topic relevance filtering
    • Add corporate policy scope validation
    • Create response length limits and formatting
    • Implement citation requirement enforcement
  2. Safety Guardrails

    • Add content moderation for inappropriate queries
    • Implement response toxicity detection
    • Create data privacy protection measures
    • Add rate limiting and abuse prevention
  3. Quality Assurance

    • Implement response coherence validation
    • Add factual accuracy checks against source material
    • Create confidence scoring for responses
    • Add fallback responses for edge cases

Implementation Details:

class ResponseGuardrails:
    def validate_query(self, query: str) -> ValidationResult
    def validate_response(self, response: str, sources: List) -> ValidationResult
    def apply_content_filters(self, content: str) -> str
    def check_citation_requirements(self, response: str) -> bool

Acceptance Criteria:

  • System refuses to answer non-policy-related questions
  • All responses include at least one source citation
  • Response length is within configured limits (default: 500 words)
  • Content moderation prevents inappropriate responses
  • Confidence scoring accurately reflects response quality
  • Comprehensive test coverage for edge cases and failure modes

PHASE 4: Web Application Enhancement 🌐

Issue #25: Chat Interface Implementation

Priority: Medium | Effort: Medium | Timeline: 1-2 weeks

Description: Create a user-friendly web interface for interacting with the RAG system.

Technical Requirements:

  • Modern chat UI with message history
  • Real-time response streaming (optional)
  • Source citation display with links to original documents
  • Mobile-responsive design
  • Error handling and loading states

Files to Create/Modify:

templates/
β”œβ”€β”€ chat.html (new)
β”œβ”€β”€ base.html (new)
static/
β”œβ”€β”€ css/
β”‚   └── chat.css (new)
β”œβ”€β”€ js/
β”‚   └── chat.js (new)

Issue #26: Document Management Interface

Priority: Low | Effort: Small | Timeline: 1 week

Description: Add administrative interface for document management and system monitoring.

Technical Requirements:

  • Document upload and processing interface
  • System health and performance dashboard
  • Search analytics and usage metrics
  • Database management tools

PHASE 5: Evaluation and Quality Assurance πŸ“Š

Issue #27: Evaluation Framework Implementation

Priority: High | Effort: Medium | Timeline: 1-2 weeks

Description: Implement comprehensive evaluation metrics for RAG response quality.

Technical Requirements:

  1. Evaluation Dataset

    • Create 25-30 test questions covering all policy domains
    • Develop "gold standard" answers for comparison
    • Include edge cases and boundary conditions
    • Add question difficulty levels and categories
  2. Automated Metrics

    • Groundedness: Verify responses are supported by retrieved context
    • Citation Accuracy: Ensure citations point to relevant source material
    • Relevance: Measure how well responses address the question
    • Completeness: Assess whether responses fully answer questions
    • Consistency: Verify similar questions get similar answers
  3. Performance Metrics

    • Latency Measurement: p50, p95, p99 response times
    • Throughput: Requests per second capacity
    • Resource Usage: Memory and CPU utilization
    • Error Rates: Track and categorize failure modes

Implementation Structure:

evaluation/
β”œβ”€β”€ __init__.py
β”œβ”€β”€ evaluation_dataset.json
β”œβ”€β”€ metrics/
β”‚   β”œβ”€β”€ groundedness.py
β”‚   β”œβ”€β”€ citation_accuracy.py
β”‚   β”œβ”€β”€ relevance.py
β”‚   └── performance.py
β”œβ”€β”€ evaluation_runner.py
└── report_generator.py

Evaluation Questions Example:

{
  "questions": [
    {
      "id": "q001",
      "category": "remote_work",
      "difficulty": "basic",
      "question": "How many days per week can employees work remotely?",
      "expected_answer": "Employees may work remotely up to 3 days per week with manager approval.",
      "expected_sources": ["remote_work_policy.md"],
      "evaluation_criteria": ["factual_accuracy", "citation_required"]
    }
  ]
}

Acceptance Criteria:

  • Evaluation dataset covers all major policy areas
  • Automated metrics provide reliable quality scores
  • Performance benchmarks establish baseline expectations
  • Evaluation reports generate actionable insights
  • Results demonstrate system meets quality requirements
  • Continuous evaluation integration for ongoing monitoring

PHASE 6: Final Documentation and Deployment πŸ“

Issue #28: Production Deployment and Documentation

Priority: Medium | Effort: Medium | Timeline: 1 week

Description: Prepare the application for production deployment with comprehensive documentation.

Technical Requirements:

  1. Production Configuration

    • Environment variable management for LLM API keys
    • Database backup and recovery procedures
    • Monitoring and alerting setup
    • Security hardening and access controls
  2. Comprehensive Documentation

    • Complete design-and-evaluation.md with architecture decisions
    • Update deployed.md with live application URLs and features
    • Finalize README.md with setup and usage instructions
    • Create API documentation with OpenAPI/Swagger specs
  3. Demonstration Materials

    • Record 5-10 minute demonstration video
    • Create slide deck explaining architecture and evaluation results
    • Prepare code walkthrough materials
    • Document key design decisions and trade-offs

Documentation Structure:

docs/
β”œβ”€β”€ architecture/
β”‚   β”œβ”€β”€ system_overview.md
β”‚   β”œβ”€β”€ api_reference.md
β”‚   └── deployment_guide.md
β”œβ”€β”€ evaluation/
β”‚   β”œβ”€β”€ evaluation_results.md
β”‚   └── performance_benchmarks.md
└── demonstration/
    β”œβ”€β”€ demo_script.md
    └── video_outline.md

Implementation Strategy

Development Approach

  1. Test-Driven Development: Write tests before implementation for all new features
  2. Incremental Integration: Build and test each component individually before integration
  3. Continuous Deployment: Maintain working deployments throughout development
  4. Performance Monitoring: Establish metrics and monitoring from the beginning

Risk Management

  1. LLM API Dependencies: Implement multiple providers with graceful fallbacks
  2. Response Quality: Establish quality gates and comprehensive evaluation
  3. Performance Scaling: Design with scalability in mind from the start
  4. Data Privacy: Ensure no sensitive data is transmitted to external APIs

Timeline Summary

  • Phase 3: 3-4 weeks (LLM integration + guardrails)
  • Phase 4: 2-3 weeks (UI enhancement + management interface)
  • Phase 5: 1-2 weeks (evaluation framework)
  • Phase 6: 1 week (documentation + deployment)

Total Estimated Timeline: 7-10 weeks for complete implementation

Success Metrics

  • Functionality: All core RAG features working as specified
  • Quality: Evaluation metrics demonstrate high response quality
  • Performance: System meets latency and throughput requirements
  • Reliability: Comprehensive error handling and graceful degradation
  • Usability: Intuitive interface with clear user feedback
  • Maintainability: Well-documented, tested, and modular codebase

Getting Started with Phase 3

Immediate Next Steps

  1. Environment Setup: Configure LLM API keys (OpenRouter/Groq)
  2. Create Issue #23: Set up detailed GitHub issue for LLM integration
  3. Design Review: Finalize prompt templates and context strategies
  4. Test Planning: Design comprehensive test cases for RAG functionality
  5. Branch Strategy: Create feat/rag-core-implementation development branch

Key Design Decisions to Make

  1. LLM Provider Selection: OpenRouter vs Groq vs others
  2. Context Window Strategy: How much context to provide to LLM
  3. Response Format: Structured vs natural language responses
  4. Conversation Management: Stateless vs conversation history
  5. Deployment Strategy: Single service vs microservices

This roadmap provides a clear path from our current semantic search system to a full-featured RAG application ready for production deployment and evaluation.