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name: ORCHESTRATION_DEBUGGING description: Troubleshoot agent & tool failures in scheduling orchestration. Use when MCP tools fail, agent communication breaks, constraint engines error, or database operations timeout. Provides systematic incident response and root cause analysis.

ORCHESTRATION_DEBUGGING

A comprehensive debugging skill for diagnosing and resolving failures in the AI-orchestrated scheduling system, including MCP tool integration, agent workflows, constraint engine, and database operations.

When This Skill Activates

• MCP Tool Failures: Timeout, connection errors, or incorrect responses
• Agent Communication Issues: Multi-agent workflows failing to coordinate
• Constraint Engine Errors: OR-Tools solver failures, constraint conflicts
• Database Operation Failures: Deadlocks, connection pool exhaustion, slow queries
• Schedule Generation Failures: Validation errors, compliance violations, infeasible schedules
• Background Task Issues: Celery worker crashes, task timeouts, queue backlogs
• API Integration Failures: Backend API errors, authentication issues, rate limiting

Overview

This skill provides structured workflows for:

1. Incident Review: Post-mortem analysis with root cause identification
2. Log Analysis: Systematic log parsing across services (backend, MCP, Celery, database)
3. Root Cause Analysis: 5-whys investigation methodology
4. Common Failure Patterns: Catalog of known issues with solutions
5. Debugging Checklist: Step-by-step troubleshooting for each component

Architecture Context

System Components

Claude Agent
    ↓ (MCP Protocol)
MCP Server (29+ tools)
    ↓ (HTTP API)
FastAPI Backend
    ↓ (SQLAlchemy)
PostgreSQL Database
    ↓ (Async Tasks)
Celery + Redis

Common Failure Points

Layer	Component	Failure Mode
Agent	Claude Code	Token limits, context overflow, skill conflicts
MCP	Tool invocation	Timeout, serialization errors, auth failures
API	FastAPI routes	Validation errors, database session issues
Service	Business logic	Constraint violations, ACGME compliance failures
Solver	OR-Tools engine	Infeasible constraints, timeout, memory exhaustion
Database	PostgreSQL	Deadlocks, connection pool exhaustion, slow queries
Tasks	Celery workers	Task timeout, serialization errors, queue backlog

Core Debugging Phases

Phase 1: DETECTION

Goal: Identify what failed and where

1. Check error visibility
   - User-facing error message
   - API response logs
   - Backend service logs
   - Database query logs
   - MCP server logs

2. Establish failure scope
   - Single request or systemic?
   - Reproducible or intermittent?
   - User-specific or system-wide?

Phase 2: DIAGNOSIS

Goal: Understand why it failed

1. Trace request path
   - Agent → MCP → API → Service → Database
   - Identify where the chain breaks

2. Collect evidence
   - Error stack traces
   - Recent code changes (git log)
   - Database state (queries, locks)
   - System resources (CPU, memory, connections)

Phase 3: RESOLUTION

Goal: Fix the issue

1. Implement fix
   - Code changes
   - Configuration updates
   - Database repairs

2. Verify fix
   - Reproduce original failure
   - Confirm fix resolves it
   - Check for regressions

Phase 4: PREVENTION

Goal: Prevent recurrence

1. Document incident
   - Root cause
   - Fix applied
   - Lessons learned

2. Implement safeguards
   - Add tests
   - Add monitoring
   - Update documentation

Workflow Files

Workflows/incident-review.md

Post-mortem template for systematic incident analysis:

• Timeline reconstruction
• Impact assessment
• Root cause identification (5-whys)
• Remediation actions
• Prevention measures

Use when: After resolving a major incident or when debugging a complex failure

Workflows/log-analysis.md

Log parsing and correlation across services:

• Log location discovery
• Error pattern extraction
• Cross-service correlation
• Timeline reconstruction
• Anomaly detection

Use when: Error is unclear or spans multiple services

Workflows/root-cause-analysis.md

5-whys investigation methodology:

• Problem statement definition
• Iterative questioning
• Evidence gathering
• Root cause identification

Use when: Surface-level fix is clear but underlying cause is not

Reference Files

Reference/common-failure-patterns.md

Catalog of known issues with symptoms and fixes:

• Database connection failures
• MCP tool timeouts
• Constraint engine errors
• Agent communication failures
• Each with: Symptoms → Diagnosis → Fix

Use when: Encountering a familiar-looking error

Reference/debugging-checklist.md

Step-by-step troubleshooting guide:

• Service health checks
• Log verification
• Database inspection
• MCP tool status
• Agent state verification

Use when: Starting investigation with no clear direction

Key Files to Inspect

Backend Logs

# Application logs
docker-compose logs backend --tail=200 --follow

# Uvicorn access logs
docker-compose logs backend | grep "POST\|GET\|PUT\|DELETE"

# Error-specific logs
docker-compose logs backend 2>&1 | grep -i "error\|exception\|failed"

MCP Server Logs

# MCP server output
docker-compose logs mcp-server --tail=100 --follow

# Tool invocation logs
docker-compose logs mcp-server | grep "tool_call\|error"

# API connectivity
docker-compose exec mcp-server curl -s http://backend:8000/health

Database Logs

# Connect to database
docker-compose exec db psql -U scheduler -d residency_scheduler

# Check active queries
SELECT pid, now() - query_start as duration, query
FROM pg_stat_activity
WHERE state != 'idle'
ORDER BY duration DESC;

# Check locks
SELECT * FROM pg_locks WHERE NOT granted;

Celery Logs

# Worker logs
docker-compose logs celery-worker --tail=100 --follow

# Beat scheduler logs
docker-compose logs celery-beat --tail=50 --follow

# Check queue status
docker-compose exec redis redis-cli LLEN celery

Output Format

Quick Status Check

SYSTEM HEALTH: [GREEN|YELLOW|ORANGE|RED]

Backend API: ✓ Responding (200ms avg)
MCP Server: ✓ Connected (29 tools available)
Database: ✓ 8/20 connections used
Celery: ✗ 3 failed tasks in queue
Redis: ✓ Connected

ISSUES DETECTED:
1. Celery worker timeout on schedule generation task
2. 2 database deadlocks in last hour

RECOMMENDED ACTION: Review celery worker logs and database lock contention

Full Incident Report

## INCIDENT REPORT: [Title]

**Date**: 2025-12-26 14:32 UTC
**Severity**: [LOW|MEDIUM|HIGH|CRITICAL]
**Status**: [INVESTIGATING|RESOLVED|MONITORING]
**Reporter**: [Agent/User/Automated]

### Summary
One-sentence description of what failed

### Timeline
- 14:30 - First error detected
- 14:31 - Service degraded
- 14:35 - Fix implemented
- 14:40 - Service restored

### Impact
- Users affected: [number or "all"]
- Data integrity: [preserved/compromised]
- ACGME compliance: [maintained/violated]
- Downtime: [duration]

### Root Cause
Detailed explanation using 5-whys methodology

### Resolution
What was done to fix the issue

### Prevention
How to prevent this in the future

### Action Items
- [ ] Add monitoring for [metric]
- [ ] Create test case for [scenario]
- [ ] Update documentation for [component]

Error Handling Best Practices

1. Preserve Context

# Bad - loses context
try:
    result = await some_operation()
except Exception:
    raise HTTPException(status_code=500, detail="Operation failed")

# Good - preserves stack trace
try:
    result = await some_operation()
except Exception as e:
    logger.error(f"Operation failed: {e}", exc_info=True)
    raise HTTPException(
        status_code=500,
        detail="Operation failed - check logs for details"
    )

2. Log Diagnostic Information

logger.info(f"Starting operation with params: {params}")
logger.debug(f"Intermediate state: {state}")
logger.error(f"Operation failed at step {step}", exc_info=True)

3. Add Request IDs

# For tracing requests across services
request_id = str(uuid.uuid4())
logger.info(f"[{request_id}] Processing schedule generation")

Integration with Other Skills

With systematic-debugger

For code-level debugging:

1. ORCHESTRATION_DEBUGGING identifies which component failed
2. systematic-debugger investigates the code

With production-incident-responder

For production emergencies:

1. production-incident-responder handles immediate crisis
2. ORCHESTRATION_DEBUGGING performs post-mortem

With automated-code-fixer

For automated fixes:

1. ORCHESTRATION_DEBUGGING identifies root cause
2. automated-code-fixer applies tested solution

Escalation Criteria

ALWAYS escalate to human when:

1. Data corruption detected
2. Security vulnerability discovered
3. ACGME compliance violated
4. Multi-hour outage
5. Root cause unclear after investigation
6. Fix requires database migration or schema change

Can handle automatically:

1. Configuration issues
2. Known failure patterns with documented fixes
3. Resource exhaustion (restart services)
4. Transient network errors
5. Log analysis and report generation

Monitoring Recommendations

After resolving incidents, add monitoring for:

• Error rate by endpoint
• Request latency (p50, p95, p99)
• Database connection pool usage
• Celery queue depth
• MCP tool success rate
• Schedule generation success rate

References

• /docs/development/DEBUGGING_WORKFLOW.md - Overall debugging methodology
• /docs/development/CI_CD_TROUBLESHOOTING.md - CI/CD specific patterns
• /mcp-server/RESILIENCE_MCP_INTEGRATION.md - MCP tool documentation
• /backend/app/core/logging.py - Logging configuration
• Workflows/ - Detailed workflow templates
• Reference/ - Common patterns and checklists