Individual skill
windows-remote-desktop-connection-doctor
Diagnoses Windows App (Remote Desktop / AVD / W365 / direct PC) connection problems on macOS: transport selection (UDP Shortpath vs WebSocket), VPN/proxy interference, and stuck "Configuring remote PC..." dialogs. Use when a VDI connection is slow/stuck, transport shows WebSocket not UDP, or Windows App freezes at a progress dialog. Not for general network diagnosis (use debugging-network-issues or tunnel-doctor).
windows-remote-desktop-connection-doctor/SKILL.md
Source commit 7c4d326ddd94d504e00e241ba49498e95160afbe
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- Last checked
- Nov 4, 2026
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- Repository last updated
- Nov 7, 2026
- License
- MIT
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# 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...".