Windows Remote Desktop Connection Doctor

Diagnoses and fixes slow or stuck Windows App (Remote Desktop / AVD / W365 / direct PC) connections on macOS using network evidence and client log forensics.

UtilitiesIntermediate★ 1,323⑂ 212AI score 8/10Last updated: Aug 8, 2026

What it does

Explains and fixes why a session fell back from UDP Shortpath to WebSocket/TCP (a big latency penalty).
Collects evidence in parallel with ifconfig, netstat -rn, lsof, scutil --proxy, and tailscale netcheck to spot VPN/proxy interference (e.g. source IP 198.18.0.x).
Parses macOS Windows App logs for decisive signatures: FetchClientOptions exception, certificate validation failures, OneAuthError_InteractionRequired, UserCancelled(8), CMSTATE_DROPPED.
Buckets root causes into six categories (VPN/proxy, ISP UDP restriction, client health-check failure, Shortpath disabled server-side, stale Microsoft account poisoning auth, server reboot from Windows Update) with fixes and verification steps.
Ships a standalone scripts/probe_rdp_server.py RDP+TLS probe that proves server health without credentials.

Who it's for

macOS users on Azure Virtual Desktop, Windows 365, or a corporate VDI.
Anyone RDP-ing directly into a home workstation that hangs at "Configuring remote PC...".
Proxy/VPN users (Clash, ShadowRocket, Tailscale) seeing laggy remote sessions.

Example uses

"RTT is 165ms and transport shows WebSocket" → traffic traced to a proxy TUN, add DIRECT rules for wvd.microsoft.com, reconnect and confirm UDP with 40–60ms RTT.
"Direct PC stuck at Configuring remote PC" → probe proves the server is healthy, log shows the OneAuth cancel chain, remove the expired work account in Windows App → Settings → Accounts and retry.
"A working session dropped and won't reconnect" → correlate UTC log CMSTATE_DROPPED with LastBootUpTime and Event ID 1074 to confirm a Windows Update restart, then set active hours.

· · · Install guide · · ·

Try it now, no install

Paste this into Claude to use the skill without installing anything.

Read the instructions in this file and follow them to help me:
https://raw.githubusercontent.com/daymade/claude-code-skills/HEAD/windows-remote-desktop-connection-doctor/SKILL.md

What I want: (describe your task here)

If Claude can't open the link, open it yourself and paste the contents instead.

↓ If it works for you, download the ZIP below and install it. Then it runs on its own — no pasting each time.

Install in the Claude app (no terminal)

Download the ZIP with the button below.
In Claude, open Settings → Capabilities and turn on 'Code execution and file creation'. (one time)
Go to Customize → Skills → + → 'Upload a skill' and upload the ZIP.

↓ Download ZIP

Install in Claude Code

Let Claude do it — paste this into Claude Code

Install the skill I found on Claude Skill Mart.
Copy the windows-remote-desktop-connection-doctor folder from the GitHub repo daymade/claude-code-skills into my ~/.claude/skills/windows-remote-desktop-connection-doctor/.
When it's done, tell me in one line what this skill can do.

Install with a command instead

git clone https://github.com/daymade/claude-code-skills.git && cp -r claude-code-skills/windows-remote-desktop-connection-doctor ~/.claude/skills/

⚠ This is a third-party skill. Check the source repository before installing.

Open Terminal on your Mac.
Clone the repository: git clone https://github.com/daymade/claude-code-skills.git
Install the skill: mkdir -p ~/.claude/skills && cp -r claude-code-skills/windows-remote-desktop-connection-doctor ~/.claude/skills/
Verify that the references/ folder and scripts/probe_rdp_server.py came along — the workflow depends on them.
Confirm Python 3 is available with python3 --version (preinstalled on macOS) for the RDP probe.
Restart Claude Code and ask something like "My Remote Desktop connection is using WebSocket instead of UDP — diagnose it."

View source on GitHub ↗License: MIT