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Windows Remote Desktop Connection Doctor

Diagnoses slow, stuck, or failing Windows App (Remote Desktop / AVD / W365 / direct PC) connections on macOS using transport-protocol and log evidence.

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

What it does

Walks through an evidence-driven diagnosis of Windows App (formerly Microsoft Remote Desktop) connection problems on macOS — for Azure Virtual Desktop, Windows 365, and direct PC-by-hostname sessions.

  • Identifies the active transport: UDP Shortpath vs. WebSocket/TCP fallback through the gateway
  • Collects network evidence with ifconfig, netstat -rn, scutil --proxy, and lsof to spot VPN/proxy TUN interference (utun devices, 198.18.0.x source IPs)
  • Parses Windows App logs under ~/Library/Containers/com.microsoft.rdc.macos/..., aggregating events by session GUID and matching signatures like FetchClientOptions exception: Request timed out, certificate validation failures, and OneAuthError_InteractionRequired
  • Sorts findings into six root-cause categories: proxy/VPN interference, ISP UDP restriction, client health-check failure, Shortpath disabled server-side, stale Microsoft work/school account poisoning auth, and Windows Update reboots
  • Ships scripts/probe_rdp_server.py for a credential-free RDP + TLS reachability probe

Who it's for

  • Mac users on corporate VDI (AVD/W365) suffering high latency or freezes
  • Remote workers whose direct-PC session hangs on "Configuring remote PC..."
  • Anyone running Clash, ShadowRocket, or Tailscale alongside RDP
  • IT helpdesk and infra engineers who need log-based proof instead of guesswork

Examples

  1. "Connection Info shows WebSocket with 165 ms RTT" — the skill checks utun routing and STUN/TURN log lines, recommends DOMAIN-SUFFIX,wvd.microsoft.com,DIRECT proxy rules, then verifies UDP sockets with lsof -i UDP.
  2. "My home PC session is stuck at Configuring remote PC" — the probe script proves port 3389 and TLS are healthy, then UserCancelled(8) plus "no valid refresh tokens" in the log points to removing an expired Microsoft account and relaunching the app.
  3. "A working session dropped and won't reconnect" — correlates CMSTATE_DROPPED with the PC's LastBootUpTime and Event ID 1074 to blame a Windows Update restart, and suggests configuring active hours.

· · · Install guide · · ·

Install in the Claude app (no terminal)
  1. Download the ZIP with the button below.
  2. In Claude, open Settings → Capabilities and turn on 'Code execution and file creation'. (one time)
  3. 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 && mkdir -p ~/.claude/skills && cp -r claude-code-skills/windows-remote-desktop-connection-doctor ~/.claude/skills/

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

  1. Open Terminal on your Mac.
  2. Clone the repository: git clone https://github.com/daymade/claude-code-skills.git
  3. Create the skills directory if needed: mkdir -p ~/.claude/skills
  4. Copy just this skill: cp -r claude-code-skills/windows-remote-desktop-connection-doctor ~/.claude/skills/
  5. Verify with ls ~/.claude/skills/windows-remote-desktop-connection-doctor — you should see SKILL.md, scripts, and references.
  6. Restart Claude Code, then ask something like "My Windows App RDP session is slow — diagnose it" to trigger the skill.
  7. Make sure python3 is available (built into macOS or via Xcode Command Line Tools) so the agent can run python3 scripts/probe_rdp_server.py <host> 3389.
View source on GitHub ↗License: MIT