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247247| A developer's requests fail with `Not signed in to the Cloud gateway — run /login.` | The machine's managed settings set `forceLoginMethod: "gateway"` or `forceLoginGatewayUrl`, and the session has no gateway sign-in. A leftover claude.ai login doesn't satisfy the requirement. | Have the developer run `/login` and complete the gateway sign-in. See also [Administrator policy requires a Cloud gateway sign-in](/docs/en/errors#administrator-policy-requires-a-cloud-gateway-sign-in). |
248248| Claude Desktop reports that its bootstrap configuration couldn't be fetched | `/user/bootstrap` returned 404: the policy matching the user doesn't carry a `desktop` key, or no policy matched. The gateway's audit log records each rejection as `desktop_bootstrap.denied` with the reason. | Add a `desktop` block to the policy that matches the user, or to the `match: {}` base layer; an empty `desktop: {}` suffices. See [Claude Desktop overlay](/docs/en/claude-apps-gateway-config#claude-desktop-overlay). |
249249| Startup shows `Gateway login is configured in managed settings, but this Claude Code build does not include Cloud gateway support.` | The installed Claude Code build predates gateway support | Have the developer update Claude Code to a release that includes Cloud gateway support |
250| Startup exits with `Administrator policy requires a Cloud gateway sign-in on this machine` | The developer's environment sets `ANTHROPIC_API_KEY` or `ANTHROPIC_AUTH_TOKEN`, their settings configure an [`apiKeyHelper`](/docs/en/settings-reference#apikeyhelper), or an API key from an earlier Claude Console login is still saved | Have the developer clear each that applies: unset the variable, remove the `apiKeyHelper` entry, or run `claude auth logout` to remove the saved key. Then have them start `claude` and sign in with `/login`. See also [Administrator policy requires a Cloud gateway sign-in](/docs/en/errors#administrator-policy-requires-a-cloud-gateway-sign-in). |
250251| Startup or `/login` reports `Claude Code may not be enabled for your organization` after a 403 on the managed settings load | The gateway, or something in front of it, answered the `/managed/settings` request with 403. The gateway's own settings route never answers 403. The status comes from the [`access_control`](/docs/en/claude-apps-gateway-config#http-tuning) IP checks or from a proxy or WAF in front of the gateway. The audit log records an IP-check denial as `access.denied` with the reason. The developer stays signed in. | Check the audit log for `access.denied` at the time of the failure and fix the `access_control` lists or the front end, then have the developer start `claude` again |
251252| CLI `/login`: `Gateway hosts must be on your organization's private network; <host> resolves to the public (or unrecognized) address <ip>` | The gateway hostname resolves to at least one public IP address. Claude Code checks each resolved address and requires every one to be private. A common cause is a dual-stack name where one family resolves to a public address, including AWS internal dual-stack load balancers, which return public-range AAAA addresses. | Have the gateway name resolve only to private addresses on developer machines. For a dual-stack name, drop the public-range record or serve a separate internal-only DNS name. See the [private-network prerequisite](/docs/en/claude-apps-gateway#prerequisites). If the address is public space your organization owns and uses internally, [declare that block](/docs/en/claude-apps-gateway#allow-a-gateway-on-public-address-space-you-own) instead. |
252253| CLI `/login`: `Gateway login would go through proxy <proxy>, which is not on a private network` | An `HTTPS_PROXY` or `HTTP_PROXY` applies to the gateway host and the proxy's hostname resolves to a public address. A proxy whose host resolves only to private addresses is allowed and doesn't trigger this error | Add the gateway host to `NO_PROXY` on the developer's machine so the connection is direct, or use a proxy whose hostname resolves to private addresses. The message names the exact `NO_PROXY` entry to add |