When an AI coding agent cannot connect on a corporate network, first test the affected product’s documented endpoint from the same machine and execution environment where the agent runs. Then check proxy compatibility, certificate trust, and firewall access—in that order. A setting that works for an editor may not apply to its AI extension or CLI, and the right fix depends on which stage of the connection is failing.
Identify what failed and where the agent runs
Before changing settings, record the exact error and the conditions that produced it. A timeout, connection reset, DNS lookup failure, proxy authentication error, and certificate verification failure point to different parts of the network path.
- Record: the agent and version, operating system, shell, exact error text, and time of failure.
- Locate the session: note whether it runs locally, over SSH, in WSL, in a container, or in an app-managed session.
- Pin down the affected action: distinguish sign-in, installation or update, model requests, streaming responses, and a single feature.
These details matter because an editor, its AI extension, and a command-line agent may use different proxy settings or network paths. For example, Claude Code documents settings scope and startup behavior that varies by session type: Claude Code corporate proxy configuration.
Test connectivity from the agent’s environment
Run the test in the same shell, machine, or app environment as the failing agent. A check from your browser or a different computer does not establish that the agent can reach its own service. Use the endpoint documented for the product you are troubleshooting; success against one vendor’s endpoint says nothing about another vendor’s service.
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GitHub Copilot
GitHub documents a verbose connectivity test for Copilot at https://copilot-proxy.githubusercontent.com/_ping:
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
A successful connection returns HTTP 200, according to GitHub. For Copilot Chat specifically, use https://api.githubcopilot.com/_ping instead. Keep the verbose output if the request fails; it can help IT identify whether the failure is at DNS resolution, connection, proxy negotiation, or the endpoint. See GitHub’s Copilot network troubleshooting steps.
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Claude Code and Cursor
For Claude Code, test the relevant host in its current network requirements; different features may need different hosts. For Cursor, start with Cursor Settings > Network > Run Diagnostics and its documented connectivity tests: Cursor network troubleshooting.
Check proxy settings and product compatibility
If direct access fails but a proxy is required, or the agent reports a proxy error, verify that the specific AI tool supports the proxy type and settings in use. Do not assume that an editor’s general proxy configuration governs its AI connection.
Claude Code
Claude Code supports the standard HTTPS_PROXY and HTTP_PROXY environment variables, as well as lowercase variants, and supports NO_PROXY in space- or comma-separated formats. Its documentation describes the order in which proxy variables are checked. It does not support SOCKS proxies. Set variables before launching Claude Code; it reads shell variables at process startup, so restart the process after changing them.
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export HTTPS_PROXY=http://proxy.example.com:8080
export HTTP_PROXY=http://proxy.example.com:8080
claude
For an app-managed Claude Desktop session, proxy values may need to be configured in managed settings or ~/.claude/settings.json. Repository settings do not control the app-managed provider connection. Check the session-specific instructions in Anthropic’s proxy guidance.
GitHub Copilot
GitHub says Copilot’s custom proxy implementation does not currently support proxy URLs beginning with https://. Its documentation lists basic authentication and Kerberos support; Kerberos requires a valid ticket and correctly configured service principal name. Verify the URL scheme and authentication method against GitHub’s supported proxy details.
Cursor streaming
A connection may reach Cursor but fail when streaming responses. Cursor’s documentation states: “Cursor uses HTTP/2 for streaming responses. Some corporate proxies (like Zscaler) block HTTP/2.” For this documented compatibility issue, open Cursor Settings > Network, set HTTP Compatibility Mode to HTTP/1.1, and restart Cursor. This workaround addresses the described Cursor streaming case; it is not a universal fix for other agents or proxy failures.
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Diagnose certificate verification errors safely
Errors mentioning a self-signed certificate, an unknown issuer, or certificate verification failure indicate a trust problem, which can occur when a corporate proxy inspects TLS and replaces the upstream certificate. Ask whether TLS inspection is active and whether the organization’s approved certificate is installed and trusted by the runtime the agent uses.
Claude Code documents operating-system certificate-store support depending on runtime and an enterprise CA option using NODE_EXTRA_CA_CERTS:
export NODE_EXTRA_CA_CERTS=/path/to/ca-cert.pem
GitHub’s guidance is to ensure the corporate certificate is installed and detected, or to ask IT to configure a policy that permits the connection. GitHub warns that disabling certificate verification can create security issues; do not use it as a routine workaround. See Claude Code certificate configuration and GitHub’s certificate guidance.
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Some organizations also require client certificates for mutual TLS (mTLS). Claude Code documents environment-variable configuration for this. Treat certificate and private-key files as sensitive credentials and follow your organization’s storage and rotation rules.
Check allowlists, DNS, and the request’s location
Proxy and firewall requirements are product-specific and can change. Ask IT to compare the affected product’s current host requirements with proxy and firewall logs. Claude Code lists hosts for API requests, sign-in, plugin downloads, and other features; Cursor documents domain patterns and separate sign-in requirements. Use the live vendor pages for the product and feature in question rather than copying another tool’s allowlist: Claude Code network requirements and Cursor network troubleshooting.
Cursor Remote SSH and VPN-related failures
For Cursor Remote SSH, AI requests are sent from the local machine to Cursor’s servers; the remote host provides file access. Check local internet access first, then investigate SSH stability and remote CPU or memory exhaustion. Cursor suggests SSH keep-alive settings and restarting Cursor after reconnecting if a dropped session left stale processes.
If DNS errors begin after a VPN disconnect, fully restart Cursor and inspect system DNS configuration: run scutil --dns on macOS or check /etc/resolv.conf on Linux. These checks help distinguish a stale or incorrect DNS state from a proxy or certificate problem.
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Escalate organization-controlled settings with useful evidence
Proxy authentication, TLS inspection, certificate deployment, and firewall allowlists are often controlled by IT. Send the administrator the exact endpoint, failure timestamp, agent and version, execution environment, full error text, and verbose connectivity-test output. Include relevant vendor diagnostic logs when available.
Claude Code can be launched with claude --debug; its documentation also describes checking the resulting log and /status for configuration state. Before sharing logs or command output, remove proxy passwords, API keys, private keys, and other secrets. Share only what your organization’s support process permits. See Claude Code proxy troubleshooting and GitHub Copilot network troubleshooting.
Quick Recap
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