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Fix the driver behind crashes, sound loss and screen glitchesFind Drivers →Clear out junk files and repair common Windows errorsFree Scan →When an AI coding agent cannot connect behind a corporate network, first identify exactly which tool and environment made the request. Then test that product’s documented endpoint from the same machine or shell, check proxy compatibility, investigate TLS trust, and compare required hosts with firewall and proxy logs. Proxy settings are product-specific: a setting that works for an editor may not work for its AI extension or command-line agent.
Start by identifying what failed
Record the exact error and the context in which it occurred before changing settings. A DNS lookup failure, ETIMEDOUT, ECONNRESET, proxy-authentication error, and certificate-verification failure point to different parts of the connection path.
- Note the agent and version, operating system, shell, and whether it runs locally, over SSH, in WSL, in a container, or in an app-managed session.
- Identify the failed stage: sign-in, installation or update, model request, streaming response, or a single feature.
- Record whether the problem began after a VPN, proxy, certificate, or network-policy change.
This distinction matters because a CLI, editor extension, and managed desktop session may use different network paths and configuration scopes. Claude Code, for example, reads shell proxy variables when its process starts; app-managed Claude Desktop connections may require managed settings or ~/.claude/settings.json, rather than repository settings. See Claude Code network configuration.
Test connectivity from the agent’s environment
Run the test from the same machine and network context as the failing agent. A successful check from your browser or a different terminal does not prove that the agent can reach its service.
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GitHub Copilot
GitHub documents this verbose ping for Copilot:
curl --verbose -i -L https://copilot-proxy.githubusercontent.com/_ping
If you know the proxy address, test through it explicitly:
curl --verbose -x http://YOUR-PROXY-URL:PORT -i -L https://copilot-proxy.githubusercontent.com/_ping
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GitHub says a successful connection returns HTTP 200. For Copilot Chat, use https://api.githubcopilot.com/_ping instead. The verbose output can help IT identify whether the request failed at DNS, connection, proxy, or TLS negotiation. These endpoints are specific to Copilot; they do not establish reachability for another provider. See GitHub’s network troubleshooting guide.
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Claude Code and Cursor
For Claude Code, test the relevant host listed in its current network requirements, rather than substituting a Copilot endpoint. Cursor provides Network > Run Diagnostics in the application; run that check and use the connectivity tests in Cursor’s troubleshooting guide.
Check proxy settings and product compatibility
Do not assume that all AI tools inherit the same proxy configuration or support the same proxy types. Confirm the affected product’s documented behavior and restart it after changing settings that are read only at launch.
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Claude Code supports standard proxy environment variables, including HTTPS_PROXY and HTTP_PROXY; lowercase variants are also supported. It reads shell variables at startup, so launch a fresh process after changing them. The documentation describes NO_PROXY in comma- or space-separated formats and states that SOCKS proxies are not supported. In app-managed Claude Desktop sessions, proxy values may need to be configured in managed settings or ~/.claude/settings.json; repository settings do not control the app-managed provider connection. Configuration details are in Claude Code’s network configuration documentation.
GitHub Copilot
Check the proxy URL scheme and authentication method. GitHub says Copilot’s custom proxy implementation does not currently support proxy URLs beginning with https://. It supports basic authentication and Kerberos; Kerberos requires a valid ticket and the correct service principal name. General proxy support in an editor does not guarantee that Copilot’s own connection path supports the same arrangement. Refer to GitHub’s troubleshooting guidance.
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If Cursor’s diagnostics point to streaming or a corporate proxy, try its documented compatibility setting: open Cursor Settings > Network, set HTTP Compatibility Mode to HTTP/1.1, and restart Cursor. Cursor explains that it uses HTTP/2 for streaming responses and that some corporate proxies block HTTP/2. This is a product-specific workaround, not a general fix for every proxy. See Cursor’s troubleshooting guide.
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Interpret certificate errors as a trust issue
Messages mentioning a self-signed certificate, unknown issuer, or certificate verification failure often indicate that TLS inspection is replacing the server certificate with one signed by a corporate certificate authority. Verify the cause with your organization’s IT team; do not treat the error as proof that the vendor endpoint is unsafe or that verification should be disabled.
Use an approved certificate configuration
Claude Code documents OS certificate-store support, depending on runtime, and the NODE_EXTRA_CA_CERTS=/path/to/ca-cert.pem setting for an enterprise CA. GitHub advises confirming that the corporate certificate is installed and detected, or asking IT to configure a policy that permits the connection. GitHub warns that ignoring certificate errors can create security risks, so disabling verification is not a routine troubleshooting fix. See Anthropic’s network configuration and GitHub’s network troubleshooting guide.
Handle client certificates carefully
Claude Code also documents mTLS environment variables for organizations that require client certificates. Treat certificate and private-key files as credentials: use your organization’s approved storage, access, and rotation process, and do not paste private-key contents into logs or support tickets. Configuration guidance is available in Claude Code’s network documentation.
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Check allowlists and where the request originates
Ask IT to compare the affected product’s live host requirements with proxy and firewall logs. A product may use separate hosts for API requests, sign-in, plugin downloads, or other features. Claude Code publishes its requirements in its network configuration guide; Cursor publishes domain patterns and separate sign-in requirements in its troubleshooting guide. Do not copy another vendor’s allowlist: hosts differ by product and can change.
Cursor Remote SSH
Cursor’s documentation says AI requests in a Remote SSH session are made from the local machine; the remote host provides file access. Check local internet access first. If connectivity drops after a VPN disconnect, fully restart Cursor and check the system DNS configuration: scutil --dns on macOS or /etc/resolv.conf on Linux. If the local connection works but the remote session still fails, check SSH stability and remote CPU and memory use. Cursor suggests SSH keep-alive settings and restarting the app after reconnecting if stale processes remain. See Cursor’s troubleshooting guide.
Give IT evidence they can act on
Proxy authentication, TLS inspection, certificate deployment, and firewall allowlisting are often organization-controlled. When a local check cannot resolve the issue, send IT the exact failing endpoint, timestamp, agent and version, environment, error text, and verbose command output. Include the product’s diagnostic logs where appropriate.
For Claude Code, claude --debug starts a debug session; its documentation also describes checking the resulting log and /status for configuration state. Before sharing logs, remove proxy passwords, API keys, tokens, and private-key material. Use the vendor’s current diagnostic instructions: Claude Code network configuration, GitHub Copilot network troubleshooting, or Cursor troubleshooting.
Quick Recap
A quick way to choose the next step
| What you observe | Next check |
|---|---|
| DNS lookup failure | Check DNS and VPN state in the environment where the agent runs; for Cursor after a VPN disconnect, restart the app and inspect system DNS. |
| Timeout or connection reset | Run the product’s documented endpoint test from that environment and ask IT to inspect proxy or firewall logs for the endpoint and timestamp. |
| Proxy authentication failure | Confirm the product supports the organization’s authentication method and that required credentials or Kerberos tickets are available; involve IT if policy-controlled. |
| Certificate verification failure | Check for TLS inspection and whether the approved corporate CA is installed and recognized; do not disable verification as a workaround. |
| Only streaming fails in Cursor | Try HTTP Compatibility Mode set to HTTP/1.1 in Cursor Settings > Network, then restart. |
| One feature or sign-in fails while another works | Check that feature’s documented hosts and the request’s actual origin; different services may use different endpoints or paths. |
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