The Tool Desk
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What a proxy preflight does—and does not—prove
Proxy connectivity and coding-agent sign-in are separate authentication layers. Proxy credentials let a client use the proxy; they do not provide a GitHub, Anthropic, OpenAI, or other provider account credential. Likewise, a successful proxy test does not prove that the agent can sign in or reach every service it uses.
Use a health or ping endpoint documented for the specific agent, if one is available. For GitHub Copilot, GitHub documents https://copilot-proxy.githubusercontent.com/_ping; Copilot Chat can use https://api.githubcopilot.com/_ping. GitHub says a reachable ping should return HTTP 200. These are Copilot-specific endpoints, not generic tests for other coding agents. See GitHub’s Copilot network troubleshooting guide.
Run a preflight from the agent’s actual environment
1. Identify the client and execution context
Record the agent and version, how it is launched (CLI, editor, desktop app, hosted runner, or sandbox), operating system, and the shell or process that starts it. A proxy variable in an interactive terminal may not reach a desktop application, service, container, or remote runner. Hosted agents and sandboxes can also have independent network controls and allowlists.
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2. Check the effective proxy settings safely
Check the settings the agent process actually receives, including proxy variables, client-specific configuration, and any NO_PROXY exclusions. Confirm that the proxy URL scheme and type are supported by that client and mode. Do not paste a proxy URL containing a username or password into logs, tickets, or chat.
There is no universal precedence rule for proxy settings: GitHub Copilot and Claude Code document different behavior. Consult the current product guidance for the exact client and session type: GitHub Copilot network settings and Claude Code enterprise network configuration.
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3. Test the intended route to a documented endpoint
For Copilot, GitHub’s documented verbose test through an HTTP proxy is:
curl --verbose -x http://YOUR-PROXY-URL:PORT -i -L https://copilot-proxy.githubusercontent.com/_pingReplace YOUR-PROXY-URL:PORT with the organization’s proxy address. For a direct comparison, GitHub’s example is:
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curl --verbose https://copilot-proxy.githubusercontent.com/_pingOnly try direct egress if organizational policy permits it. A response from the Copilot ping demonstrates that this request reached that endpoint at that time; it does not confirm access to other provider hosts, optional features, or the agent’s own sign-in service. Use the provider’s documented endpoint for other agents rather than reusing the Copilot URL.
4. Test proxy authentication using a supported method
Authentication methods differ by product. GitHub Copilot documents basic authentication and Kerberos; Kerberos may require a valid service ticket and the correct service principal name (SPN). Claude Code documents basic credentials in a proxy URL and recommends a compatible gateway when advanced methods such as NTLM or Kerberos are required. Check the current documentation for your exact client and version, and use your organization’s approved secret-handling process rather than hardcoding passwords in scripts.
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5. Check TLS trust without disabling verification
If the proxy inspects TLS, the client may need the organization-approved certificate authority (CA) configured or installed. GitHub documents OS trust and NODE_EXTRA_CA_CERTS; Claude Code documents bundled or system trust stores and NODE_EXTRA_CA_CERTS. If certificate validation fails, ask IT to confirm the intended interception and certificate chain. Do not routinely bypass certificate verification: GitHub warns that ignoring certificate errors can create security risks. The applicable guidance is in the Copilot network settings and Claude Code proxy documentation.
6. Verify provider access and agent sign-in separately
Compare the provider’s current endpoint or allowlist requirements with the organization’s firewall and proxy policy, including optional services needed by the intended workflow. Then use the agent’s own documented login or credential check. For example, GitHub documents Copilot CLI authentication and credential lookup separately; its CLI does not support a classic personal access token. See Authenticating GitHub Copilot CLI.
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For hosted or sandboxed use, check the network configuration for that environment, not only the local machine. GitHub’s documentation covers the Copilot allowlist and cloud-agent development environment. Those requirements can depend on the agent, runner, and enabled features.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.How to interpret common results
| Observation | What it may indicate | Next check |
|---|---|---|
| DNS failure or connection refused | Name resolution, routing, a blocked listener, firewall policy, or an incorrect proxy address. | Confirm the proxy host and port, DNS resolution, network route, and whether the proxy listener is reachable from this execution context. |
| Proxy authentication challenge or denial | Missing or rejected credentials, or an authentication method the client does not support. | Confirm the required method and credentials with the proxy administrator; check product support for that method. |
| Timeout or connection reset | Several possible network conditions, including routing, filtering, proxy behavior, or a remote service issue. | Use verbose output and ask IT to correlate the time, destination, and proxy logs rather than assuming a single cause. |
| Certificate-chain or signature error | The client may not trust the CA used for TLS inspection, or the presented chain may not match the expected configuration. | Verify the approved CA setup and certificate chain with IT; do not disable TLS verification as a routine workaround. |
| Successful HTTP response from the endpoint | The request reached that destination successfully, but other hosts, agent features, or provider sign-in may still fail. | Check the endpoint list for the intended workflow and perform the agent’s own documented sign-in check. |
These results are diagnostic clues, not definitive proof of a root cause. GitHub’s troubleshooting guide recommends verbose curl output and editor diagnostics when investigating Copilot network errors.
Why proxy behavior varies by coding agent
Do not assume that one client’s proxy configuration applies to another. Check the current official documentation for the exact product, version, mode, and execution environment.
| Client or environment | Documented details relevant to a preflight | Scope to keep in mind |
|---|---|---|
| GitHub Copilot | Documents basic HTTP proxy setups, basic authentication and Kerberos, custom certificates, and environment-variable precedence. It says an https:// proxy URL is unsupported for Copilot. |
Kerberos can require a valid ticket and correct SPN. Consult GitHub’s network settings for current details. |
| Claude Code | Documents proxy environment variables, NO_PROXY, basic credentials, custom CA settings, and client certificates for mutual TLS (mTLS). |
SOCKS proxies are unsupported. Configuration behavior can differ for some Claude Desktop-managed sessions; see the enterprise network documentation. |
| OpenAI CLI | The CLI reference says HTTP and SOCKS proxies are supported, but HTTPS proxies are rejected in the documented mTLS mode. | This statement is scoped to that CLI and mode; it does not establish behavior for every OpenAI product or authentication setup. See the OpenAI CLI reference. |
| Hosted agents and sandboxes | May have separate proxy variables, certificate settings, network rules, or endpoint allowlists. | Requirements depend on the agent, runner, and enabled features. Consult the relevant Copilot allowlist and cloud-agent environment guidance when applicable. |
What to send IT or support
Share enough sanitized detail to distinguish a route, authentication, TLS, allowlist, or agent-login problem:
Quick Recap
- Agent, client, and version; operating system; and whether the failure occurs in a terminal, editor, desktop app, container, hosted runner, or sandbox.
- Proxy scheme and host, with usernames, passwords, and other credentials removed.
- Exact destination host and path, test time, command shape, HTTP status or error class, and whether TLS verification succeeded.
- Relevant verbose output or editor diagnostics after removing tokens, passwords, authorization headers, private-key contents, and sensitive internal hostnames.
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