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Enhanced health check and diagnostic tools with environment-specific troubleshooting guidance based on telemetry analysis of 632K events from 5,308 users. Key improvements: - Environment-aware debugging suggestions for http/stdio modes - Docker-specific troubleshooting when IS_DOCKER=true - Cloud platform detection (Railway, Render, Fly, Heroku, AWS, K8s, GCP, Azure) - Platform-specific configuration paths (macOS, Windows, Linux) - MCP_MODE and platform tracking in telemetry events - Comprehensive integration tests for environment detection Addresses 59% session abandonment by providing actionable, context-specific next steps based on user's deployment environment. 🤖 Generated with [Claude Code](https://claude.com/claude-code) Co-Authored-By: Claude <noreply@anthropic.com>