diff --git a/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.test.ts b/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.test.ts
index e82e3afea7303..c15ce3932bb80 100644
--- a/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.test.ts
+++ b/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.test.ts
@@ -1,11 +1,13 @@
 import * as NodeCrypto from "@effect/platform-node/NodeCrypto";
 import { assert, describe, it } from "@effect/vitest";
+import * as Clock from "effect/Clock";
 import * as Deferred from "effect/Deferred";
 import * as Duration from "effect/Duration";
 import * as Effect from "effect/Effect";
 import * as Fiber from "effect/Fiber";
 import * as Layer from "effect/Layer";
 import * as Ref from "effect/Ref";
+import * as Result from "effect/Result";
 import * as HttpClient from "effect/http/HttpClient";
 import * as HttpClientRequest from "effect/http/HttpClientRequest";
 import * as HttpClientResponse from "effect/http/HttpClientResponse";
@@ -238,4 +240,34 @@ describe("DesktopLocalEnvironmentAuth", () => {
       assert.strictEqual(yield* Ref.get(requestCount), 1);
     }).pipe(Effect.provide(TestClock.layer())),
   );
+
+  it.effect("waits through a backend that stalls for 30 seconds after it is ready", () =>
+    Effect.gen(function* () {
+      const requestCount = yield* Ref.make(0);
+      const layerHttpClient = Layer.succeed(
+        HttpClient.HttpClient,
+        HttpClient.make((request) =>
+          Effect.gen(function* () {
+            yield* Ref.update(requestCount, (count) => count + 1);
+            const now = yield* Clock.currentTimeMillis;
+            return now < 30_000 ? yield* Effect.never : tokenResponse(request);
+          }),
+        ),
+      );
+      const auth = yield* DesktopLocalEnvironmentAuth.DesktopLocalEnvironmentAuth.pipe(
+        Effect.provide(
+          DesktopLocalEnvironmentAuth.layer.pipe(
+            Layer.provide(Layer.mergeAll(layerPool, layerHttpClient, NodeCrypto.layerMac)),
+          ),
+        ),
+      );
+
+      const fiber = yield* auth.getBearerToken.pipe(Effect.result, Effect.forkChild);
+      yield* TestClock.adjust(Duration.seconds(45));
+      const result = yield* Fiber.join(fiber);
+
+      assert.isTrue(Result.isSuccess(result));
+      assert.strictEqual(yield* Ref.get(requestCount), 4);
+    }).pipe(Effect.provide(TestClock.layer())),
+  );
 });
diff --git a/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.ts b/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.ts
index 6c7d24623d40f..89aa3cd2a678c 100644
--- a/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.ts
+++ b/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.ts
@@ -17,7 +17,8 @@ import * as HttpClient from "effect/http/HttpClient";
 
 import * as DesktopBackendPool from "./DesktopBackendPool.ts";
 
-const BOOTSTRAP_TRANSIENT_RETRY_TIMEOUT = Duration.seconds(15);
+// Each /oauth/token attempt may take 10 s, so a backend busy after ready needs several attempts.
+const BOOTSTRAP_TRANSIENT_RETRY_TIMEOUT = Duration.seconds(60);
 const BOOTSTRAP_TRANSIENT_RETRY_INTERVAL = Duration.millis(500);
 const TRANSIENT_BOOTSTRAP_STATUS_CODES = new Set([502, 503, 504]);