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Based on my experience, here's the troubleshooting workflow I'd recommend for Cloud Sync issues: Phase 1: Initial Checks Check sync status in Azure Portal: Entra ID → Cloud sync → Configurations Check provisioning logs: Entra ID → Monitoring → Prov...

The Actual root cause: Installing AADCloudSyncTools & prerequisites After changing the UPNs and restarting services, I was still getting timeouts. In desperation, I turned to Microsoft's documentation and discovered the AADCloudSyncTools PowerShell m...

The Potential root cause: UPN Domain Mismatch After hours of troubleshooting, I discovered a possible root cause. My on-premises users had UPNs like: Testuser@main.KMTHomelab.com SamuelGreeb@main.KMTHomelab.com But in Azure, my only verified doma...

The Problem → *.msappproxy.net issue Even after getting users to sync, I noticed errors in the provisioning logs about connectivity to *.msappproxy.net endpoints. The agent was intermittently losing connection to Azure. The *.msappproxy.net issue is ...
