diff --git a/src/betterAuth.ts b/src/betterAuth.ts
index 5012c542ac..5326c8bc71 100644
--- a/src/betterAuth.ts
+++ b/src/betterAuth.ts
@@ -298,6 +298,9 @@ export const getBetterAuthOptions = (pool: Pool): BetterAuthOptions => {
     basePath: '/auth',
     secret: process.env.BETTER_AUTH_SECRET ?? '',
     trustedOrigins,
+    onAPIError: {
+      errorURL: `${process.env.COMMENTS_PREFIX}/callback`,
+    },
     secondaryStorage: {
       get: (key) => singleRedisClient.get(`ba:${key}`),
       set: (key, value, ttl) =>
diff --git a/src/routes/betterAuth.ts b/src/routes/betterAuth.ts
index a838204b1c..d0ac98b407 100644
--- a/src/routes/betterAuth.ts
+++ b/src/routes/betterAuth.ts
@@ -119,6 +119,57 @@ export const logoutBetterAuth = async (
   }
 };
 
+const isOAuthCallbackPath = (url: string): boolean =>
+  /\/auth\/callback\//.test(url);
+
+const rewriteOAuthErrorRedirect = (
+  request: FastifyRequest,
+  response: Response,
+): string | undefined => {
+  if (!isOAuthCallbackPath(request.url)) {
+    return undefined;
+  }
+
+  if (response.status < 300 || response.status >= 400) {
+    return undefined;
+  }
+
+  const location = response.headers.get('location');
+  if (!location) {
+    return undefined;
+  }
+
+  const webappCallback = `${process.env.COMMENTS_PREFIX}/callback`;
+  if (!webappCallback) {
+    return undefined;
+  }
+
+  if (location.startsWith(webappCallback)) {
+    return undefined;
+  }
+
+  let redirectUrl: URL;
+  try {
+    redirectUrl = new URL(location, `${request.protocol}://${request.host}`);
+  } catch {
+    return undefined;
+  }
+
+  const hasError =
+    redirectUrl.searchParams.has('error') ||
+    redirectUrl.searchParams.get('state') === 'state_not_found';
+  if (!hasError) {
+    return undefined;
+  }
+
+  const callbackUrl = new URL(webappCallback);
+  redirectUrl.searchParams.forEach((value, key) => {
+    callbackUrl.searchParams.set(key, value);
+  });
+
+  return callbackUrl.toString();
+};
+
 const betterAuthRoute = async (fastify: FastifyInstance): Promise<void> => {
   // Apple sends OAuth callbacks as application/x-www-form-urlencoded POSTs.
   // Fastify does not parse this content type by default, so collect the raw
@@ -142,6 +193,18 @@ const betterAuthRoute = async (fastify: FastifyInstance): Promise<void> => {
           reply,
           body,
         });
+
+        const rewrittenUrl = rewriteOAuthErrorRedirect(request, response);
+        if (rewrittenUrl) {
+          request.log.warn(
+            { originalLocation: response.headers.get('location') },
+            'OAuth callback error redirect rewritten to webapp',
+          );
+          reply.header('location', rewrittenUrl);
+          reply.status(302);
+          return reply.send();
+        }
+
         return sendBetterAuthResponse(reply, response);
       } catch (error) {
         return sendBetterAuthError(
diff --git a/src/routes/redirects.ts b/src/routes/redirects.ts
index 7687dcfb30..528891ee59 100644
--- a/src/routes/redirects.ts
+++ b/src/routes/redirects.ts
@@ -171,9 +171,29 @@ const redirectToProfileImage = async (
 export default async function (fastify: FastifyInstance): Promise<void> {
   const con = await createOrGetConnection();
 
-  fastify.get('/', (req, res) =>
-    res.redirect('https://r.daily.dev/api-redirect'),
-  );
+  fastify.get('/', (req, res) => {
+    // Some OAuth providers (e.g. GitHub) redirect cancellations to the
+    // API root instead of the BetterAuth callback URL. Forward the error
+    // params to the webapp callback so the popup can close cleanly.
+    const { error, state } = req.query as Record<string, string>;
+    if (error && state) {
+      const webappOrigin = process.env.COMMENTS_PREFIX;
+      if (webappOrigin) {
+        req.log.warn(
+          { error, state },
+          'OAuth error redirected to API root, forwarding to webapp callback',
+        );
+        const callbackUrl = new URL(`${webappOrigin}/callback`);
+        const params = new URLSearchParams(req.url.split('?')[1] ?? '');
+        params.forEach((value, key) => {
+          callbackUrl.searchParams.set(key, value);
+        });
+        return res.redirect(callbackUrl.toString());
+      }
+    }
+
+    return res.redirect('https://r.daily.dev/api-redirect');
+  });
   fastify.get('/landing', (req, res) => res.redirect('https://daily.dev'));
   fastify.get('/tos', (req, res) => res.redirect('https://daily.dev/tos'));
   fastify.get('/privacy', (req, res) =>