diff --git a/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.test.ts b/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.test.ts
index bd844624d8b6..3f0bd82d5888 100644
--- a/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.test.ts
+++ b/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.test.ts
@@ -1,8 +1,11 @@
 import { assert, describe, it } from "@effect/vitest";
+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 HttpClient from "effect/http/HttpClient";
+import * as HttpClientRequest from "effect/http/HttpClientRequest";
 import * as HttpClientResponse from "effect/http/HttpClientResponse";
 import { PRIMARY_LOCAL_ENVIRONMENT_ID } from "@t3tools/contracts";
 import {
@@ -144,4 +147,91 @@ describe("DesktopLocalEnvironmentAuth", () => {
         );
       }).pipe(Effect.provide(TestClock.layer())),
   );
+
+  const tokenResponse = (request: HttpClientRequest.HttpClientRequest) =>
+    HttpClientResponse.fromWeb(
+      request,
+      new Response(
+        JSON.stringify({
+          access_token: "desktop-bearer-token",
+          issued_token_type: "urn:ietf:params:oauth:token-type:access_token",
+          token_type: "Bearer",
+          expires_in: 3600,
+          scope: "orchestration:read",
+        }),
+        { status: 200, headers: { "content-type": "application/json" } },
+      ),
+    );
+  const layerPool = Layer.succeed(DesktopBackendPool.DesktopBackendPool, {
+    list: Effect.succeed([
+      {
+        id: PRIMARY_LOCAL_ENVIRONMENT_ID,
+        label: Effect.succeed("Windows"),
+        currentConfig: Effect.succeedSome(config),
+      },
+    ]),
+  } as unknown as DesktopBackendPool.DesktopBackendPool["Service"]);
+  // Answers the first `failures` exchanges with `failure`, then with a token.
+  const makeExchange = (failures: number, failure: () => Response) =>
+    Effect.gen(function* () {
+      const requestCount = yield* Ref.make(0);
+      const layerHttpClient = Layer.succeed(
+        HttpClient.HttpClient,
+        HttpClient.make((request) =>
+          Ref.updateAndGet(requestCount, (count) => count + 1).pipe(
+            Effect.map((count) =>
+              count <= failures
+                ? HttpClientResponse.fromWeb(request, failure())
+                : tokenResponse(request),
+            ),
+          ),
+        ),
+      );
+      const auth = yield* DesktopLocalEnvironmentAuth.DesktopLocalEnvironmentAuth.pipe(
+        Effect.provide(
+          DesktopLocalEnvironmentAuth.layer.pipe(
+            Layer.provide(Layer.mergeAll(layerPool, layerHttpClient)),
+          ),
+        ),
+      );
+      return { auth, requestCount };
+    });
+
+  it.effect("retries a backend that is still starting", () =>
+    Effect.gen(function* () {
+      const { auth, requestCount } = yield* makeExchange(
+        2,
+        () => new Response("", { status: 503 }),
+      );
+
+      const fiber = yield* auth.getBearerToken.pipe(Effect.forkChild);
+      yield* TestClock.adjust(Duration.seconds(1));
+
+      assert.strictEqual(yield* Fiber.join(fiber), "desktop-bearer-token");
+      assert.strictEqual(yield* Ref.get(requestCount), 3);
+    }).pipe(Effect.provide(TestClock.layer())),
+  );
+
+  it.effect("does not retry a rejected bootstrap credential", () =>
+    Effect.gen(function* () {
+      const { auth, requestCount } = yield* makeExchange(1, () =>
+        Response.json(
+          {
+            _tag: "EnvironmentAuthInvalidError",
+            code: "auth_invalid",
+            reason: "invalid_credential",
+            traceId: "trace-1",
+          },
+          { status: 401 },
+        ),
+      );
+
+      const fiber = yield* auth.getBearerToken.pipe(Effect.flip, Effect.forkChild);
+      yield* TestClock.adjust(Duration.seconds(1));
+      const error = yield* Fiber.join(fiber);
+
+      assert.strictEqual(error._tag, "DesktopLocalEnvironmentAuthSessionBootstrapError");
+      assert.strictEqual(yield* Ref.get(requestCount), 1);
+    }).pipe(Effect.provide(TestClock.layer())),
+  );
 });
diff --git a/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.ts b/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.ts
index 51109f8a4ecf..d137d502e6c5 100644
--- a/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.ts
+++ b/apps/desktop/src/backend/DesktopLocalEnvironmentAuth.ts
@@ -1,18 +1,41 @@
 import { bootstrapRemoteBearerSession } from "@t3tools/client-runtime/authorization";
+import type { RemoteEnvironmentRequestError } from "@t3tools/client-runtime/rpc";
 import { PRIMARY_LOCAL_ENVIRONMENT_ID } from "@t3tools/contracts";
 import { currentDesktopBootstrapToken } from "@t3tools/shared/desktopBootstrapToken";
 import * as Clock from "effect/Clock";
 import * as Context from "effect/Context";
+import * as Duration from "effect/Duration";
 import * as Effect from "effect/Effect";
 import * as Layer from "effect/Layer";
 import * as Option from "effect/Option";
 import * as Ref from "effect/Ref";
+import * as Schedule from "effect/Schedule";
 import * as Schema from "effect/Schema";
 import * as Semaphore from "effect/Semaphore";
 import * as HttpClient from "effect/http/HttpClient";
 
 import * as DesktopBackendPool from "./DesktopBackendPool.ts";
 
+// A loopback /oauth/token exchange can fail transiently while the backend
+// settles (a 502-504, a refused or reset connection, a timeout). Retry those
+// for as long as the renderer's own bootstrap does; a rejected credential or a
+// server error is final.
+const BOOTSTRAP_TRANSIENT_RETRY_TIMEOUT = Duration.seconds(15);
+const BOOTSTRAP_TRANSIENT_RETRY_INTERVAL = Duration.millis(500);
+const TRANSIENT_BOOTSTRAP_STATUS_CODES = new Set([502, 503, 504]);
+
+const isTransientBearerBootstrapError = (error: RemoteEnvironmentRequestError): boolean => {
+  switch (error._tag) {
+    case "RemoteEnvironmentAuthFetchError":
+    case "RemoteEnvironmentAuthTimeoutError":
+      return true;
+    case "RemoteEnvironmentAuthUndeclaredStatusError":
+      return TRANSIENT_BOOTSTRAP_STATUS_CODES.has(error.status);
+    default:
+      return false;
+  }
+};
+
 export class DesktopLocalEnvironmentAuthBackendNotConfiguredError extends Schema.TaggedError<DesktopLocalEnvironmentAuthBackendNotConfiguredError>()(
   "DesktopLocalEnvironmentAuthBackendNotConfiguredError",
   {},
@@ -86,6 +109,12 @@ export const make = Effect.gen(function* () {
           },
         }).pipe(
           Effect.provideService(HttpClient.HttpClient, httpClient),
+          Effect.retry({
+            while: isTransientBearerBootstrapError,
+            schedule: Schedule.spaced(BOOTSTRAP_TRANSIENT_RETRY_INTERVAL),
+          }),
+          // Bounds the attempts and any request still in flight at the deadline.
+          Effect.timeout(BOOTSTRAP_TRANSIENT_RETRY_TIMEOUT),
           Effect.mapError(
             (cause) =>
               new DesktopLocalEnvironmentAuthSessionBootstrapError({