Tunnel Doctor

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

Diagnostic Workflow

Step 1: Identify the Symptom

Determine which scenario applies:

• Tailscale ping works, SSH works, but curl/HTTP times out → HTTP proxy env var conflict (Step 2A)
• Tailscale ping works, SSH/TCP times out → Route conflict (Step 2B)
• SSH connects but operation not permitted → Tailscale SSH config issue (Step 4)
• SSH connects but be-child ssh exits code 1 → WSL snap sandbox issue (Step 5)

Key distinction: SSH does NOT use http_proxy/NO_PROXY env vars, but curl/wget/Python requests/Node.js fetch do. If SSH works but HTTP doesn’t, it’s almost always a proxy env var issue, not a route issue.

Step 2A: Fix HTTP Proxy Environment Variables

Check if proxy env vars are intercepting Tailscale HTTP traffic:

env | grep -i proxy

Broken output — proxy is set but NO_PROXY doesn’t exclude Tailscale:

http_proxy=http://127.0.0.1:1082
https_proxy=http://127.0.0.1:1082
NO_PROXY=localhost,127.0.0.1          ← Missing Tailscale!

Fix — add Tailscale MagicDNS domain + CIDR to NO_PROXY:

export NO_PROXY=localhost,127.0.0.1,.ts.net,100.64.0.0/10,192.168.*,10.*,172.16.*

Two layers complement each other: .ts.net handles domain-based access, 100.64.0.0/10 handles direct IP access.

NO_PROXY syntax pitfalls — see references/proxy_fixes.md for the compatibility matrix.

Verify the fix:

# Both must return HTTP 200:
NO_PROXY="...(new value)..." curl -s --connect-timeout 5 http://<host>.ts.net:<port>/health -w "HTTP %{http_code}\n"
NO_PROXY="...(new value)..." curl -s --connect-timeout 5 http://<tailscale-ip>:<port>/health -w "HTTP %{http_code}\n"

Then persist in shell config (~/.zshrc or ~/.bashrc).

Step 2B: Detect Route Conflicts

Check if a proxy tool hijacked the Tailscale CGNAT range:

route -n get <tailscale-ip>

Healthy output — traffic goes through Tailscale interface:

destination: 100.64.0.0
interface: utun7    # Tailscale interface (utunN varies)

Broken output — proxy hijacked the route:

destination: 100.64.0.0
gateway: 192.168.x.1    # Default gateway
interface: en0           # Physical interface, NOT Tailscale

Confirm with full route table:

netstat -rn | grep 100.64

Two competing routes indicate a conflict:

100.64/10  192.168.x.1   UGSc  en0       ← Proxy added this (wins)
100.64/10  link#N        UCSI  utun7     ← Tailscale route (loses)

Root cause: On macOS, UGSc (Static Gateway) takes priority over UCSI (Cloned Static Interface) for the same prefix length.

Step 3: Fix Proxy Tool Configuration

Identify the proxy tool and apply the appropriate fix. See references/proxy_fixes.md for detailed instructions per tool.

Key principle: Do NOT use tun-excluded-routes to exclude 100.64.0.0/10. This causes the proxy to add a → en0 route that overrides Tailscale. Instead, let the traffic enter the proxy TUN and use a DIRECT rule to pass it through.

Universal fix — add this rule to any proxy tool:

IP-CIDR,100.64.0.0/10,DIRECT
IP-CIDR,fd7a:115c:a1e0::/48,DIRECT

After applying fixes, verify:

route -n get <tailscale-ip>
# Should show Tailscale utun interface, NOT en0

Step 4: Configure Tailscale SSH ACL

If SSH connects but returns operation not permitted, the Tailscale ACL may require browser authentication for each connection.

At Tailscale ACL admin, ensure the SSH section uses "action": "accept":

"ssh": [
    {
        "action": "accept",
        "src": ["autogroup:member"],
        "dst": ["autogroup:self"],
        "users": ["autogroup:nonroot", "root"]
    }
]

Note: "action": "check" requires browser authentication each time. Change to "accept" for non-interactive SSH access.

Step 5: Fix WSL Tailscale Installation

If SSH connects and ACL passes but fails with be-child ssh exit code 1 in tailscaled logs, the snap-installed Tailscale has sandbox restrictions preventing SSH shell execution.

Diagnosis — check WSL tailscaled logs:

# For snap installs:
sudo journalctl -u snap.tailscale.tailscaled -n 30 --no-pager

# For apt installs:
sudo journalctl -u tailscaled -n 30 --no-pager

Look for:

access granted to user@example.com as ssh-user "username"
starting non-pty command: [/snap/tailscale/.../tailscaled be-child ssh ...]
Wait: code=1

Fix — replace snap with apt installation:

# Remove snap version
sudo snap remove tailscale

# Install apt version
curl -fsSL https://tailscale.com/install.sh | sh

# Start with SSH enabled
sudo tailscale up --ssh

Important: The new installation may assign a different Tailscale IP. Check with tailscale status --self.

Step 6: Verify End-to-End

Run a complete connectivity test:

# 1. Check route is correct
route -n get <tailscale-ip>

# 2. Test TCP connectivity
nc -z -w 5 <tailscale-ip> 22

# 3. Test SSH
ssh -o ConnectTimeout=10 -o StrictHostKeyChecking=no <user>@<tailscale-ip> 'echo SSH_OK && hostname && whoami'

All three must pass. If step 1 fails, revisit Step 3. If step 2 fails, check WSL sshd or firewall. If step 3 fails, revisit Steps 4-5.

References

• references/proxy_fixes.md — Detailed fix instructions for Shadowrocket, Clash, and Surge