Windows Remote Desktop Connection Doctor

Diagnose and fix Windows App (Microsoft Remote Desktop / AVD / WVD / W365 / direct PC) connection issues on macOS, with focus on transport protocol optimization and root-cause falsification.

Methodology base: the general evidence-driven diagnosis discipline lives in the debugging-network-issues skill. This skill is the Windows-App / AVD transport domain layer — it leans toward connection-quality optimization more than root-cause falsification, so the methodology overlap is lighter.

Background

Azure Virtual Desktop transport priority: UDP Shortpath > TCP > WebSocket. UDP Shortpath provides the best experience (lowest latency, supports UDP Multicast). When it fails, the client falls back to WebSocket over TCP 443 through the gateway, adding significant latency overhead.

Direct PC connections use plain RDP over TCP 3389 (usually TLS-wrapped). They have no Connection Info panel, no gateway reachability tests, and no transport optimization step. For direct PC, the dominant failure modes are:

1. The remote PC is off or unreachable (network/firewall).
2. The Windows App client has a stale or expired Microsoft work/school account that poisons the auth orchestration, leaving the connection stuck at "Configuring remote PC...".
3. The remote PC rebooted (often Windows Update), and the client cannot recover cleanly.

This skill handles both scenarios.

Diagnostic Workflow