# Implementation Plan
- [x] 1. Enhance core logger with safe JSON serialization and fallback mechanisms
- Add safe JSON serialization with circular reference detection
- Implement fallback to console logging when structured logging fails
- Add enhanced error handling for logging operations
- Update logger configuration to support new options
- _Requirements: 4.1, 4.2, 4.3_
- [x] 2. Create ServerLogger wrapper for server-specific logging
- Create ServerLogger class that wraps ConfigurableLogger
- Add methods for server lifecycle events (startup, shutdown, tool registration)
- Add proper error context preservation for server errors
- Include server metadata in log entries
- _Requirements: 1.1, 1.2, 1.3, 2.3_
- [ ] 3. Create CLIOutputManager for separating CLI output from logs
- Create CLIOutputManager class for handling CLI-specific output
- Implement methods for help, version, and documentation output to stdout
- Implement CLI error output that goes to stderr but isn't structured
- Ensure CLI output doesn't interfere with structured logging
- _Requirements: 3.1, 3.2, 3.3, 3.4_
- [ ] 4. Replace direct console calls in server.ts with structured logging
- Replace all console.error calls in server startup with ServerLogger
- Replace all console.error calls in server shutdown with ServerLogger
- Replace tool registration console output with structured logging
- Update error handling to use structured logging instead of console.error
- _Requirements: 1.1, 1.2, 1.3, 2.1_
- [ ] 5. Update CLI module to use CLIOutputManager and separate output streams
- Update help output to use CLIOutputManager and stdout
- Update version output to use CLIOutputManager and stdout
- Update documentation generation to use CLIOutputManager and stdout
- Update CLI error handling to use appropriate output streams
- _Requirements: 3.1, 3.2, 3.3, 3.5_
- [ ] 6. Update error handling in utils/errors.ts to use consistent logging
- Replace direct console.error calls with structured logger
- Ensure error logging uses safe JSON serialization
- Add proper error context and metadata to structured logs
- Maintain fallback behavior for critical logging failures
- _Requirements: 2.1, 2.3, 4.1, 4.4_
- [ ] 7. Add comprehensive unit tests for enhanced logging functionality
- Test safe JSON serialization with circular references
- Test fallback behavior when structured logging fails
- Test ServerLogger methods and server event logging
- Test CLIOutputManager output stream separation
- _Requirements: 4.1, 4.2, 4.3, 4.4_
- [ ] 8. Add integration tests for complete logging workflow
- Test server startup/shutdown logging cycle
- Test mixed CLI and server operations with proper output separation
- Test log parsing with external JSON parsers
- Test error scenarios and fallback mechanisms
- _Requirements: 2.1, 2.2, 3.4, 3.5_
- [ ] 9. Update logger configuration and documentation
- Update default logger configuration for production structured logging
- Add configuration examples for different deployment scenarios
- Update README with logging configuration guidance
- Add migration guide for existing deployments
- _Requirements: 3.5, 4.2_
