RDP on an Entra-Joined Machine: The Two Problems Nobody Warns You About

I have been remoting into Windows machines for over a decade. Domain-joined, workgroup, across VPNs, across the internet. RDP is one of those things that just works once you flip the toggle and open port 3389. Until it does not. This week I spent hours chasing an RDP failure on an Entra-joined machine. The machine was on the same subnet, on the same switch, plugged into the same network as the…