Outlook Calendar Two-Way Sync
Legacy Windows-based sync service with 8% error rate processing 500K+ events annually for high-volume users, causing significant client complaints
Led complete modernization effort migrating from .NET Framework 4 to .NET 8 and Windows App Service to Linux containers
- Designed distributed rate-limiting system using semaphores and mutex locks to manage Microsoft Graph API throttling across 2 instances with 4 Hangfire servers
- Implemented event-driven architecture for real-time bidirectional synchronization
- Built attachment syncing functionality from scratch
- Rewrote ~50% of codebase, retiring legacy code while maintaining zero-downtime deployments
- Established monitoring infrastructure using Datadog for error tracking and Uptime for availability metrics