tunnel-doctor
Tunnel Doctor
Diagnose and fix conflicts when Tailscale coexists with proxy/VPN tools on macOS, with specific guidance for SSH access to WSL instances.
Five Conflict Layers
Proxy/VPN tools on macOS create conflicts at five independent layers. Layers 1-3 affect Tailscale connectivity; Layer 4 affects SSH git operations; Layer 5 affects VM/container runtimes:
| Layer | What breaks | What still works | Root cause |
|---|---|---|---|
| 1. Route table | Everything (SSH, curl, browser) | tailscale ping |
tun-excluded-routes adds en0 route overriding Tailscale utun |
| 2. HTTP env vars | curl, Python requests, Node.js fetch |
SSH, browser | http_proxy set without NO_PROXY for Tailscale |
| 3. System proxy (browser) | Browser only (HTTP 503) | SSH, curl (both with/without proxy) |
Browser uses VPN system proxy; DIRECT rule routes via Wi-Fi, not Tailscale utun |
| 4. SSH ProxyCommand double tunnel | git push/pull (intermittent) |
ssh -T (small data) |
connect -H creates HTTP CONNECT tunnel redundant with Shadowrocket TUN; landing proxy drops large/long-lived transfers |
| 5. VM/Container proxy propagation | docker pull, docker build |
Host curl, running containers |
VM runtime (OrbStack/Docker Desktop) auto-injects or caches proxy config; removing proxy makes it worse (VM traffic via TUN → TLS timeout) |
Diagnostic Workflow
Step 1: Identify the Symptom
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