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Tunnel Doctor

Category: Engineering  ·  Sub-category: devops  ·  Last updated:
tool:dockertype:debug
Diagnoses and fixes conflicts between Tailscale and proxy/VPN tools (Shadowrocket, Clash, Surge) on macOS. Covers five conflict layers - (1) route hijacking, (2) HTTP proxy env var interception, (3) system proxy bypass, (4) SSH ProxyCommand double tunneling, and (5) VM/container runtime proxy propagation (OrbStack/Docker). Includes SOP for remote development via SSH tunnels with proxy-safe Makefile patterns. Use when Tailscale ping works but SSH/HTTP times out, when browser returns 503 but curl works, when git push fails with "failed to begin relaying via HTTP", when Docker pull times out behind TUN/VPN, when setting up Tailscale SSH to WSL instances, or when bootstrapping remote dev environments over Tailscale.

About this skill (catalog notes)

Tunnel Doctor includes a dedicated installation section; 57 code blocks for direct copy-paste. At roughly 5,404 words the SKILL.md is on the longer end of the catalog distribution.

Original author
ndesv21
Indexed lastmod
Catalog position
Engineering · devops
Indexed related skills
10

How Tunnel Doctor fits the catalog

Tunnel Doctor sits in the Engineering category under the devops sub-topic in the ClaudSkills catalog. There are 10 related skills indexed alongside it; comparing a few before installing usually reveals which fits your workflow best.

These notes are auto-generated from features detected in the SKILL.md file and from this catalog's structure — they aren't part of the source repository.

From the source SKILL.md

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

What this skill does

Tunnel Doctor is a community-contributed Claude Code skill in the devops sub-category. It ships as a SKILL.md file that Claude Code auto-discovers under ~/.claude/skills/tunnel-doctor/ and loads when your prompt matches the skill's trigger.

When to invoke it: Use when Tailscale ping works but SSH/HTTP times out, when browser returns 503 but curl works, when git push fails with "failed to begin relaying via HTTP", when Docker pull times out behind TUN/VPN, when setting up Tailscale SSH to WSL instances, or when bootstrapping remote dev environments over Tailscale.

Who uses this skill

The Tunnel Doctor Claude Code skill is built for software engineers, backend developers, full-stack teams, and technical leads building and maintaining production systems. It's part of ClaudSkills (also referred to as Claude Skills or Claude Code Skills) — the open community-curated registry of 117,000+ SKILL.md files for Anthropic's Claude Code agent and the wider Claude ecosystem (Claude API, Claude Agent SDK).

How to install

Free

Manual install (2 steps)

mkdir -p ~/.claude/skills/tunnel-doctor
curl -L https://claudskills.com/skills/tunnel-doctor/SKILL.md \
  -o ~/.claude/skills/tunnel-doctor/SKILL.md

Or just download SKILL.md directly and drop it into ~/.claude/skills/tunnel-doctor/. Claude Code auto-discovers it on next session.

Skills live at ~/.claude/skills/tunnel-doctor/SKILL.md on macOS/Linux, or %USERPROFILE%\.claude\skills\tunnel-doctor\SKILL.md on Windows. See the full install guide for step-by-step instructions.

Telegram

📱 Install from your phone or desktop Telegram

Open @claudskills_bot on Telegram, tap Open Desktop App, and the desktop app installs this skill for you. Or share the bot link with a colleague — they get the same one-tap install. Learn more →

Pro

One-click install via the desktop app

The ClaudSkills desktop app installs any skill directly into ~/.claude/skills/ with one click — no terminal required. Pro starts at $9/mo or $149 lifetime.

Pro

For the full experience including quality scoring and one-click install features for each skill — upgrade to Pro.

Frequently asked questions

How do I install the Tunnel Doctor Claude Code skill?
Install via the ClaudSkills desktop app (one click) or copy SKILL.md from the source repository to ~/.claude/skills/tunnel-doctor/SKILL.md and restart Claude Code. Both flows are detailed at claudskills.com/install/.
What does the Tunnel Doctor skill do?
Diagnoses and fixes conflicts between Tailscale and proxy/VPN tools (Shadowrocket, Clash, Surge) on macOS. Covers five conflict layers - (1) route hijacking, (2) HTTP proxy env var interception, (3) system proxy bypass, (4) SSH ProxyCommand double tunneling, and (5) VM/container runtime proxy propagation (OrbStack/Docker). Includes SOP for remote development via SSH tunnels with proxy-safe Makefile patterns. Use when Tailscale ping works but SSH/HTTP times out, when browser returns 503 but curl works, when git push fails with "failed to begin relaying via HTTP", when Docker pull times out behind TUN/VPN, when setting up Tailscale SSH to WSL instances, or when bootstrapping remote dev environments over Tailscale.
Is this skill free to install?
Yes. ClaudSkills is an open registry — every skill keeps its source repository's license, and manual install via copy is free. ClaudSkills Pro ($9/mo, $79/yr, or $149 one-time) adds one-click install via the desktop app and a multi-signal Quality Score.
When should I use the Tunnel Doctor skill?
Use Tunnel Doctor when your Claude Code task falls under the Engineering category — specifically in the devops area. Claude Code auto-discovers installed skills and invokes the right one based on the task description, so you can also ask Claude directly (e.g. "use Tunnel Doctor" or describe the task and let Claude pick). Browse related skills at /category/engineering/.
What is a Claude Code skill and how does the Tunnel Doctor skill fit in?
A Claude Code skill is a SKILL.md file that lives under ~/.claude/skills/<name>/ and tells the Claude Code CLI agent how to perform a specific task (instructions, prompts, allowed tools). Skills are auto-discovered at session start. Tunnel Doctor is one of 67,000+ skills indexed in the open ClaudSkills catalog, classified under the Engineering category. Learn more at /learn/what-is-a-claude-skill/.

Attribution & license

Cite this skill

If you reference this skill in a blog post, paper, or documentation, you can cite it as:

APA
ndesv21. (2026). Tunnel Doctor [Claude Code skill]. ClaudSkills. https://claudskills.com/skills/tunnel-doctor/
BibTeX
@misc{tunnel-doctor-2026,
  author    = {ndesv21},
  title     = {Tunnel Doctor [Claude Code skill]},
  year      = {2026},
  publisher = {ClaudSkills},
  url       = {https://claudskills.com/skills/tunnel-doctor/}
}

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