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A request through the tunnel can fail at one of three layers; diagnose them in order: the outbound connection to the tunnel edge, the inner TLS from Anthropic to your proxy, then routing and IP validation toward the upstream MCP server.
| Symptom | Cause | Fix |
|---|---|---|
| Tunnel doesn't appear in the agent + MCP Server picker | The picker only lists tunnels in the session's workspace that have at least one active certificate. | Register a CA certificate, or open the session in the workspace the tunnel was created in. |
Caller sees HTTP 500; cloudflared logs No ingress rules were defined | cloudflared has no local target. | Add --url http://localhost:8080 and network_mode: "service:mcp-proxy" to the cloudflared service. |
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Proxy logs no route for host |
tunnel_domain doesn't match the assigned domain, or config.yaml was edited without restarting. |
Set tunnel_domain to the exact domain shown on the tunnel detail page, then restart the proxy (docker compose restart mcp-proxy). |
Proxy logs IP validation failed: <ip> is not a private address | Upstream MCP server resolves outside RFC1918. | See Upstream IP validation. |
Proxy exits with cannot unmarshal !!seq into map[string]string | routes is a YAML list. | Use routes: { name: http://host:port }. |
Proxy exits with open /data/tls.key: permission denied | The key is 0600; the proxy container runs non-root. | chmod 644 data/tls.key. |
curl https://<proxy>:8080 fails with wrong version number | Expected; the listener is plaintext WebSocket. TLS happens inside the WS stream. | Verify through a Managed Agent or the Messages API instead. |
The following sections cover failures that need more than a one-line fix.
OAuth flows fail when your authorization server's source-IP allowlist blocks Anthropic's backend from reaching /token, /register, and the discovery endpoints. If you'd rather not allowlist Anthropic's egress ranges, you can route the backend-to-backend OAuth calls through the tunnel while keeping the browser-facing /authorize endpoint on your existing public hostname.
Add a proxy route for the authorization server
routes:
mcp: http://your-mcp-server:8080
auth: http://your-auth-server:8080Restart the proxy after editing routes (docker compose restart mcp-proxy, or helm upgrade).
Serve split-endpoint discovery metadata
Your authorization server's /.well-known/oauth-authorization-server response should point authorization_endpoint at your existing allowlisted hostname and everything else at the tunnel:
{
"issuer": "https://auth.<tunnel-domain>",
"authorization_endpoint": "https://<your-allowlisted-host>/authorize",
"token_endpoint": "https://auth.<tunnel-domain>/token",
"registration_endpoint": "https://auth.<tunnel-domain>/register",
"code_challenge_methods_supported": ["S256"]
}Point the MCP server at the tunnel issuer
Your MCP server's /.well-known/oauth-protected-resource response should reference the tunnel hostname as its authorization server:
{
"resource": "https://mcp.<tunnel-domain>",
"authorization_servers": ["https://auth.<tunnel-domain>"]
}With this configuration, the user's browser hits /authorize on your existing hostname (which your allowlist already permits), while Anthropic's backend reaches /token, /register, and the discovery documents through the tunnel.
The setup component (Helm Job or Compose setup service) authenticates to the Tunnels API by exchanging an OIDC JWT through your federation rule. When the exchange fails, see Troubleshoot a failed exchange in the Workload Identity Federation reference; the failure modes (subject, audience, issuer, JWKS, lifetime) are the same.
Tunnels-specific causes:
api.anthropic.com (no scheme). If your rule's audience is https://api.anthropic.com, set api.wif.audience to match.403 from the Tunnels API after a successful exchange means the rule's scope doesn't include org:manage_tunnels, or the rule's service account isn't a member of the tunnel's workspace. Set the scope and add the service account to the workspace.On Helm, the setup component runs as a pre-install hook Job. On failure, the Job is left behind for inspection (kubectl logs job/mcp-tunnel-setup -n mcp-tunnel). Helm doesn't manage hook resources, so delete it before retrying:
helm uninstall mcp-tunnel -n mcp-tunnel
kubectl -n mcp-tunnel delete job mcp-tunnel-setupCheck the cloudflared logs first. Common causes:
TUNNEL_TOKEN is missing, expired, or copied incorrectly.cloudflared may also log warnings about UDP receive buffer sizes; this is a QUIC tuning hint, not an error.
When Anthropic rejects the proxy's certificate during inner TLS, the proxy logs tls handshake failed. Verify that:
*.<tunnel-domain>.See the certificate requirements for the full validation rules.
For SSRF protection, the proxy only dials addresses in the RFC1918 private ranges (10.0.0.0/8, 172.16.0.0/12, 192.168.0.0/16) by default. Only IPv4 is supported for the proxy-to-upstream connection. (The cloudflared-to-edge egress range in Network requirements is a different hop.)
If the proxy logs IP validation failed: <ip> is not a private address, the upstream hostname resolved outside that set. On Kubernetes, some managed distributions allocate the Service CIDR outside RFC1918; if kubectl get svc kubernetes -n default -o jsonpath='{.spec.clusterIP}' returns an address outside the private ranges, look up your cluster's Service CIDR and add it.
If the address is legitimate, add the narrowest covering CIDR to upstream.allowed_ips. Setting allowed_ips replaces the RFC1918 default rather than extending it, so include the private ranges your other upstream MCP servers use:
upstream:
allowed_ips:
- 10.0.0.0/8
- 172.16.0.0/12
- 192.168.0.0/16
- 127.0.0.0/8 # loopback, for local testing onlyAvoid 0.0.0.0/0 outside of local testing; it disables SSRF protection entirely.