diff --git a/src/shared/__tests__/api-errors.test.ts b/src/shared/__tests__/api-errors.test.ts
index 8de03727f..288c32c8d 100644
--- a/src/shared/__tests__/api-errors.test.ts
+++ b/src/shared/__tests__/api-errors.test.ts
@@ -1,6 +1,7 @@
 import { AxiosError, AxiosHeaders, type AxiosResponse } from 'axios';
 import axios from 'axios';
 import { analytics } from '@utils/analytics';
+import { detectRegion } from '@utils/urls';
 import {
   diagnoseApiError,
   fetchProjectData,
@@ -9,6 +10,11 @@ import {
 } from '../api';
 
 vi.mock('@utils/debug', () => ({ logToFile: vi.fn() }));
+// Dev builds pin localhost, which skips the us/eu probe.
+vi.mock(import('@shared/constants'), async (importOriginal) => ({
+  ...(await importOriginal()),
+  IS_DEV: false,
+}));
 vi.mock('@utils/analytics', () => ({
   analytics: { captureException: vi.fn() },
 }));
@@ -93,6 +99,16 @@ describe('retryTransient', () => {
 });
 
 describe('handleApiError', () => {
+  it('says the request timed out', () => {
+    const error = handleApiError(
+      networkError(AxiosError.ECONNABORTED),
+      'fetch project data',
+    );
+
+    expect(error.message).toContain('fetch project data (timed out)');
+    expect(error.networkCode).toBe('ECONNABORTED');
+  });
+
   it('names the host and code when no response came back', () => {
     const error = handleApiError(
       networkError('ECONNRESET'),
@@ -254,3 +270,17 @@ describe('fetchProjectData failure analytics', () => {
     );
   });
 });
+
+describe('detectRegion', () => {
+  afterEach(() => vi.restoreAllMocks());
+
+  it('names the network cause when no region answers', async () => {
+    vi.spyOn(axios, 'get').mockRejectedValue(
+      networkError('SELF_SIGNED_CERT_IN_CHAIN'),
+    );
+
+    await expect(detectRegion('token')).rejects.toThrow(
+      'intercepting HTTPS to us.posthog.com',
+    );
+  });
+});
diff --git a/src/shared/api.ts b/src/shared/api.ts
index ce9eb4e35..15515ef34 100644
--- a/src/shared/api.ts
+++ b/src/shared/api.ts
@@ -4,7 +4,7 @@ import { analytics } from '@utils/analytics';
 import { logToFile } from '@utils/debug';
 import { httpsProxyConfigured } from './http-proxy';
 import { checkCertificateChain, UNTRUSTED_CERT_CODES } from './tls-check';
-import { WIZARD_USER_AGENT } from './constants';
+import { LOGIN_REQUEST_TIMEOUT_MS, WIZARD_USER_AGENT } from './constants';
 import type { HostResolution } from './host-resolution';
 
 /**
@@ -167,6 +167,8 @@ export class ApiError extends Error {
     public readonly endpoint?: string,
     /** Set after a TLS check: whether the OS store would verify the host's chain. */
     public readonly systemStoreTrusts?: boolean,
+    /** Node's error code when no response came back, such as `ECONNRESET`. */
+    public readonly networkCode?: string,
   ) {
     super(message);
     this.name = 'ApiError';
@@ -219,14 +221,10 @@ function describeAxiosFailure(error: unknown): string {
 }
 
 /** Why a fetch failed, as exception properties a query can filter on. */
-function failureProperties(
-  error: unknown,
-  apiError: ApiError,
-): Record<string, unknown> {
+function failureProperties(apiError: ApiError): Record<string, unknown> {
   return {
     status_code: apiError.statusCode,
-    network_code:
-      axios.isAxiosError(error) && !error.response ? error.code : undefined,
+    network_code: apiError.networkCode,
     system_store_trusts: apiError.systemStoreTrusts,
   };
 }
@@ -242,6 +240,7 @@ export async function fetchUserData(
           Authorization: `Bearer ${accessToken}`,
           'User-Agent': WIZARD_USER_AGENT,
         },
+        timeout: LOGIN_REQUEST_TIMEOUT_MS,
       }),
     );
 
@@ -251,7 +250,7 @@ export async function fetchUserData(
     analytics.captureException(apiError, {
       endpoint: '/api/users/@me/',
       baseUrl,
-      ...failureProperties(error, apiError),
+      ...failureProperties(apiError),
     });
     throw apiError;
   }
@@ -312,6 +311,7 @@ export async function fetchProjectData(
           Authorization: `Bearer ${accessToken}`,
           'User-Agent': WIZARD_USER_AGENT,
         },
+        timeout: LOGIN_REQUEST_TIMEOUT_MS,
       }),
     );
 
@@ -322,7 +322,7 @@ export async function fetchProjectData(
       endpoint: `/api/projects/${projectId}/`,
       baseUrl,
       projectId,
-      ...failureProperties(error, apiError),
+      ...failureProperties(apiError),
     });
     throw apiError;
   }
@@ -572,12 +572,17 @@ export async function diagnoseApiError(
     undefined,
     error.config?.url,
     result?.systemStoreTrusts,
+    error.code,
   );
 }
 
 function unreachableMessage(error: AxiosError, operation: string): string {
   const host = hostOf(error) ?? 'PostHog';
-  const code = error.code ?? 'no response';
+  // Axios reports its own timeout as ECONNABORTED, which reads as a reset.
+  const code =
+    error.code === AxiosError.ECONNABORTED
+      ? 'timed out'
+      : error.code ?? 'no response';
   if (isLocalHost(error)) {
     return `Couldn't reach ${host} to ${operation} (${code}). Check that your local server is running.`;
   }
@@ -599,6 +604,8 @@ export function handleApiError(error: unknown, operation: string): ApiError {
         unreachableMessage(axiosError, operation),
         undefined,
         endpoint,
+        undefined,
+        axiosError.code,
       );
     }
 
diff --git a/src/shared/constants.ts b/src/shared/constants.ts
index 9975c0daf..9f6b324f9 100644
--- a/src/shared/constants.ts
+++ b/src/shared/constants.ts
@@ -381,3 +381,6 @@ export const AGENTIC_DETECTION_RETRY_TIMEOUT_MS = 90_000;
  * from approval to submit the code — not how long this window may stay open.
  */
 export const OAUTH_TIMEOUT_MS = 1_800_000;
+
+/** Per request on the login path, so a dropped connection fails rather than hangs. */
+export const LOGIN_REQUEST_TIMEOUT_MS = 30_000;
diff --git a/src/shared/utils/urls.ts b/src/shared/utils/urls.ts
index bb10a19af..8be236c27 100644
--- a/src/shared/utils/urls.ts
+++ b/src/shared/utils/urls.ts
@@ -1,5 +1,10 @@
 import axios from 'axios';
-import { IS_DEV, WIZARD_USER_AGENT } from '@shared/constants';
+import { handleApiError } from '@shared/api';
+import {
+  IS_DEV,
+  LOGIN_REQUEST_TIMEOUT_MS,
+  WIZARD_USER_AGENT,
+} from '@shared/constants';
 import type { CloudRegion } from './types';
 
 /**
@@ -77,13 +82,25 @@ export async function detectRegion(
   };
 
   const [usResult, euResult] = await Promise.allSettled([
-    axios.get('https://us.posthog.com/api/users/@me/', { headers }),
-    axios.get('https://eu.posthog.com/api/users/@me/', { headers }),
+    axios.get('https://us.posthog.com/api/users/@me/', {
+      headers,
+      timeout: LOGIN_REQUEST_TIMEOUT_MS,
+    }),
+    axios.get('https://eu.posthog.com/api/users/@me/', {
+      headers,
+      timeout: LOGIN_REQUEST_TIMEOUT_MS,
+    }),
   ]);
 
   if (usResult.status === 'fulfilled') return 'us';
   if (euResult.status === 'fulfilled') return 'eu';
 
+  // Neither region answered: a network cause, not the token.
+  const reason: unknown = usResult.reason;
+  if (axios.isAxiosError(reason) && !reason.response) {
+    throw handleApiError(reason, 'find your PostHog region');
+  }
+
   throw new Error(
     'Could not determine cloud region from access token. Please check your PostHog account.',
   );
diff --git a/src/tui/auth/__tests__/oauth.test.ts b/src/tui/auth/__tests__/oauth.test.ts
index 03678a133..94690c01c 100644
--- a/src/tui/auth/__tests__/oauth.test.ts
+++ b/src/tui/auth/__tests__/oauth.test.ts
@@ -1,5 +1,7 @@
+import axios, { AxiosError, AxiosHeaders } from 'axios';
 import {
   assertWizardCompletionScope,
+  exchangeCodeForToken,
   extractOAuthCode,
   isAuthorizationTimeout,
 } from '../oauth';
@@ -126,3 +128,24 @@ describe('wizard OAuth scopes', () => {
     ]);
   });
 });
+
+describe('exchangeCodeForToken', () => {
+  afterEach(() => vi.restoreAllMocks());
+
+  it('names the cause when the token endpoint gives no response', async () => {
+    const config = {
+      url: 'https://oauth.posthog.com/oauth/token',
+      headers: new AxiosHeaders(),
+    };
+    vi.spyOn(axios, 'post').mockRejectedValue(
+      new AxiosError('failed', 'SELF_SIGNED_CERT_IN_CHAIN', config, {}),
+    );
+
+    await expect(
+      exchangeCodeForToken('code', 'verifier', 'http://localhost:8239'),
+    ).rejects.toMatchObject({
+      networkCode: 'SELF_SIGNED_CERT_IN_CHAIN',
+      message: expect.stringContaining('intercepting HTTPS') as string,
+    });
+  });
+});
diff --git a/src/tui/auth/oauth.ts b/src/tui/auth/oauth.ts
index 40c91d295..dd53dcdc9 100644
--- a/src/tui/auth/oauth.ts
+++ b/src/tui/auth/oauth.ts
@@ -2,6 +2,7 @@ import * as crypto from 'node:crypto';
 import * as http from 'node:http';
 import { execSync } from 'node:child_process';
 import axios from 'axios';
+import { ApiError, handleApiError } from '@shared/api';
 import {
   getOAuthClientId,
   missingOAuthScopes,
@@ -10,6 +11,7 @@ import {
 } from '@programs';
 import type { OAuthTokenResponse } from '@programs/types';
 import {
+  LOGIN_REQUEST_TIMEOUT_MS,
   OAUTH_PORTS,
   OAUTH_TIMEOUT_MS,
   WIZARD_USER_AGENT,
@@ -348,7 +350,8 @@ function isPortInUseError(error: unknown): boolean {
   );
 }
 
-async function exchangeCodeForToken(
+/** Exported for tests. */
+export async function exchangeCodeForToken(
   code: string,
   codeVerifier: string,
   callbackUrl: string,
@@ -374,6 +377,7 @@ async function exchangeCodeForToken(
           'Content-Type': 'application/json',
           'User-Agent': WIZARD_USER_AGENT,
         },
+        timeout: LOGIN_REQUEST_TIMEOUT_MS,
       },
     );
   } catch (e) {
@@ -395,6 +399,10 @@ async function exchangeCodeForToken(
       );
       throw exchangeError;
     }
+    // No response: name the cause rather than axios's bare message.
+    if (axios.isAxiosError(e) && !e.response) {
+      throw handleApiError(e, 'finish logging in');
+    }
     throw e;
   }
 
@@ -629,6 +637,8 @@ export async function performOAuthFlow(
           step: 'oauth_flow',
           oauth_error_code: oauthErrorCode,
           oauth_error_description: flowError?.description,
+          network_code:
+            error instanceof ApiError ? error.networkCode : undefined,
           client_id: clientId,
           requested_scopes: config.scopes.join(' '),
           // Collapse OAuth callback failures of the same kind into one issue