tunnel-doctor

Name: tunnel-doctor
Availability: InStock
Author: huubar

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

Ready to run

npx skills add https://github.com/HuuBar/skill-routing-experiment --skill tunnel-doctor

💬 Prompt for ChatGPT / Claude Chat▼

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.