This is the skill you reach for when Tailscale ping works but SSH or HTTP mysteriously times out on macOS, or when your browser returns 503 but curl succeeds. It methodically walks through six conflict layers between Tailscale and proxy tools like Shadowrocket, Clash, or Surge: route hijacking, HTTP proxy environment variables, system proxy bypass, SSH ProxyCommand double tunneling, VM runtime proxy propagation in Docker and OrbStack, and stalled DNS resolvers that cause 60 second hangs. The diagnostic tables are excellent at distinguishing symptoms that look similar but have different root causes. It also covers SSH access to WSL instances over Tailscale, which has its own trap involving snap sandbox restrictions.

skills.sh installs
713
GitHub stars
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last updated
Aug 21, 2026

Install

$ npx -y skills add daymade/claude-code-skills --skill tunnel-doctor --agent claude-code

Installs into .claude/skills of the current project.

Files

Tunnel Doctor

Diagnose and fix conflicts when Tailscale coexists with proxy/VPN tools on macOS, with specific guidance for SSH access to WSL instances.

Methodology base: the general diagnostic discipline this skill builds on — evidence over assumption, falsification over confirmation, layered isolation, counter-review — lives in the debugging-network-issues skill. This skill is the macOS Tailscale⨯proxy domain layer on top of it; reach for the base skill when the symptom is not a known Tailscale/proxy conflict.

Ownership boundary: this skill owns concrete local network-path operations: Tailscale, route/DNS/proxy interception, VM/WSL propagation, TUN forwarding planes, and proxy node/exit/chain capacity. Use debugging-network-issues as the general method when the boundary is still unknown or the symptom belongs to SSE/CDN/application protocol behavior. This keeps one concrete operator instead of forcing the user to choose between two overlapping proxy doctors.

Target and task scope

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Details

Repository
github.com/daymade/claude-code-skills
Categories
Backend & APIs, DevOps & CI/CD, Git & Pull Requests, Debugging, Automation & Workflows, Python
First seen
Jun 3, 2026

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