skills.rest
HuuBar
HuuBarCOMMUNITY
Explore all skills by this author →
GitHub

tunnel-doctor

Diagnoses macOS networking conflicts between Tailscale and proxy/VPN tools.

Updated Apr 21, 2026
Search Tags:#git#vpn#macos#ssh#tailscale#network-diagnostics#proxy-conflicts
One-click install
npx skills add https://github.com/HuuBar/skill-routing-experiment --skill tunnel-doctor
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: tunnel-doctor
Source: https://github.com/HuuBar/skill-routing-experiment/tree/main/unified_skills/daymade/tunnel-doctor
Command: npx skills add https://github.com/HuuBar/skill-routing-experiment --skill tunnel-doctor

SYSTEM DOCUMENTATION & REQUIREMENTS

💡 This Skill includes scripts (resource) and references (resource) components.

What problem does it solve?

Diagnoses and fixes conflicts that prevent Tailscale from coexisting with proxy/VPN tools on macOS, covering five conflict layers including route hijacking, HTTP proxy environment variables, system proxy bypass, SSH ProxyCommand double tunneling, and VM/container proxy propagation.

Core Features & Use Cases

  • Diagnostic workflow for common conflict scenarios across macOS when Tailscale traffic is misrouted.
  • Prescribed fixes for route hijack, proxy envs, system proxy bypass, and SSH/git proxy pitfalls to restore reliable connectivity.
  • Real-world use cases include SSH access to remote Macs, Git operations through proxies, and Docker/VM networking with Shadowrocket/Clash/Surge active.
  • Example: diagnose why browser shows 503 while curl succeeds and apply a DIRECT rule + NO_PROXY tweaks.

Quick Start

Run the Tunnel Doctor quick diagnose to identify the active proxy conflict layer and apply the recommended fixes.

Frequently Asked Questions about tunnel-doctor

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
Why does Tailscale ping work but SSH times out on macOS?▼

Tailscale ping succeeding while SSH times out indicates a macOS proxy conflict or SSH ProxyCommand double tunneling. Traffic is misrouted by active VPN tools, requiring route checks and proxy config validation to restore connectivity.

How do I fix Git operations failing through an SSH proxy with Tailscale active?▼

To fix Git operations failing through an SSH proxy with Tailscale active, diagnose the SSH config for double tunneling and adjust NO_PROXY environment variables. This resolves HTTP tunnel issues and restores reliable Git connectivity.

Why does my browser return a 503 error while curl succeeds when using Tailscale?▼

A browser returning 503 while curl succeeds happens when system proxy bypass rules misroute Tailscale traffic. Applying a DIRECT proxy rule alongside NO_PROXY environment tweaks ensures the browser routes traffic correctly.

Does Tunnel Doctor diagnose macOS networking conflicts with Shadowrocket and Clash?▼

Tunnel Doctor diagnoses macOS networking conflicts between Tailscale and proxy tools like Shadowrocket, Clash, and Surge. It validates VM and container proxy propagation to ensure reliable end-to-end connectivity across active VPN environments.

What is the best way to manage NO_PROXY environment variables for Tailscale on macOS?▼

The best way to manage NO_PROXY variables for Tailscale is running a prescribed diagnostic workflow to identify active proxy conflict layers. This applies targeted fixes to route hijacking and system proxy bypass configurations.

Related Skills

Explore More Software Engineering Skills→
plurigridplurigrid
60

network

Coordinates ssh, curl, nmap and Tailscale for remote Linux administration and diagnostics.

Official
Advanced
dmzoneilldmzoneill
2

network-connectivity-check

Diagnoses network connectivity issues via ping, port, and protocol checks.

Community
Intermediate
ManuelKugelmannManuelKugelmann
3

claude-get-session-info

Export CLAUDE_PID and SESSION_ID variables by sourcing a shell script.

Community
Basic
magnus919magnus919
40

headscale-derp

Deploy and manage DERP relay servers for Tailscale and Headscale networks.

Community
Advanced