diff --git a/apps/web/src/authBootstrap.test.ts b/apps/web/src/authBootstrap.test.ts
index 65c6f8edd3424..f444c64cb16ad 100644
--- a/apps/web/src/authBootstrap.test.ts
+++ b/apps/web/src/authBootstrap.test.ts
@@ -8,6 +8,7 @@ import {
 import { createBrowserHistory } from "@tanstack/react-router";
 import * as DateTime from "effect/DateTime";
 import * as Effect from "effect/Effect";
+import { HttpClientError, HttpClientRequest } from "effect/http";
 import { afterEach, beforeEach, describe, expect, it, vi } from "vite-plus/test";
 
 import { installEnvironmentHttpTest } from "../test/environmentHttpTest";
@@ -165,6 +166,54 @@ describe("resolveInitialServerAuthGateState", () => {
     expect(testApi.calls.browserSession).toEqual([{ credential: "desktop-bootstrap-token" }]);
   });
 
+  it("retries the desktop bootstrap while the backend is still unreachable", async () => {
+    const nextSession = sequence(
+      unauthenticatedSession(DESKTOP_AUTH),
+      authenticatedSession(DESKTOP_AUTH),
+    );
+    const testApi = await installAuthApi({
+      session: nextSession,
+      browserSession: () => Effect.succeed(browserSession(["orchestration:read", "access:write"])),
+    });
+    // What FetchHttpClient yields when nothing listens on the backend port.
+    const connectionRefused = new HttpClientError.HttpClientError({
+      reason: new HttpClientError.TransportError({
+        request: HttpClientRequest.get("http://localhost:3773/api/auth/session"),
+        cause: new TypeError("Failed to fetch"),
+      }),
+    });
+    let unreachableAttempts = 1;
+    __setPrimaryHttpRunnerForTests((effect) => {
+      if (unreachableAttempts > 0) {
+        unreachableAttempts -= 1;
+        return Promise.reject(connectionRefused);
+      }
+      return testApi.run(effect);
+    });
+
+    const testWindow = installTestBrowser("http://localhost/");
+    testWindow.desktopBridge = {
+      getLocalEnvironmentBootstraps: () => [
+        {
+          id: "primary",
+          label: "Local",
+          httpBaseUrl: "http://localhost:3773",
+          wsBaseUrl: "ws://localhost:3773",
+          bootstrapToken: "desktop-bootstrap-token",
+        },
+      ],
+    } as unknown as DesktopBridge;
+
+    const { resolveInitialServerAuthGateState } = await import("./environments/primary");
+
+    vi.useFakeTimers({ toFake: ["setTimeout", "Date"] });
+    await Promise.all([
+      expect(resolveInitialServerAuthGateState()).resolves.toEqual({ status: "authenticated" }),
+      vi.advanceTimersByTimeAsync(1_000),
+    ]);
+    expect(testApi.calls.browserSession).toEqual([{ credential: "desktop-bootstrap-token" }]);
+  });
+
   it("takes a pairing token from the location hash and strips it immediately", async () => {
     const testWindow = installTestBrowser("http://localhost/#token=pairing-token");
     const { takePairingTokenFromUrl } = await import("./environments/primary");
diff --git a/apps/web/src/environments/primary/auth.ts b/apps/web/src/environments/primary/auth.ts
index e9affcfbdd727..988cd3b04a873 100644
--- a/apps/web/src/environments/primary/auth.ts
+++ b/apps/web/src/environments/primary/auth.ts
@@ -291,7 +291,7 @@ function waitForBootstrapRetry(delayMs: number): Promise<void> {
 
 function isTransientBootstrapError(error: unknown): boolean {
   if (isPrimaryEnvironmentRequestError(error)) {
-    return TRANSIENT_BOOTSTRAP_STATUS_CODES.has(error.status);
+    return TRANSIENT_BOOTSTRAP_STATUS_CODES.has(error.status) || isTransportError(error.cause);
   }
 
   if (error instanceof TypeError) {
@@ -301,6 +301,10 @@ function isTransientBootstrapError(error: unknown): boolean {
   return error instanceof DOMException && error.name === "AbortError";
 }
 
+function isTransportError(error: unknown): boolean {
+  return HttpClientError.isHttpClientError(error) && error.reason._tag === "TransportError";
+}
+
 async function bootstrapServerAuth(urlCredential: string | null): Promise<ServerAuthGateState> {
   const currentSession = await fetchSessionState();
   if (currentSession.authenticated && !urlCredential) {
diff --git a/apps/web/test/environmentHttpTest.ts b/apps/web/test/environmentHttpTest.ts
index 93843cff65c9d..50e6cc36fe95a 100644
--- a/apps/web/test/environmentHttpTest.ts
+++ b/apps/web/test/environmentHttpTest.ts
@@ -23,7 +23,7 @@ import { HttpApiTest } from "effect/http-api";
 import * as HttpApiBuilder from "effect/http-api/HttpApiBuilder";
 
 import { PrimaryEnvironmentHttpClient } from "../src/environments/primary/httpClient";
-import { __setPrimaryHttpRunnerForTests } from "../src/lib/runtime";
+import { __setPrimaryHttpRunnerForTests, type PrimaryHttpEffectRunner } from "../src/lib/runtime";
 
 type BrowserSessionHandler = (
   payload: AuthBrowserSessionRequest,
@@ -125,10 +125,12 @@ export async function installEnvironmentHttpTest(scenario: EnvironmentHttpTestSc
   );
 
   const runtime = ManagedRuntime.make(Layer.succeed(PrimaryEnvironmentHttpClient, client));
-  __setPrimaryHttpRunnerForTests((effect) => runtime.runPromise(effect));
+  const run: PrimaryHttpEffectRunner = (effect) => runtime.runPromise(effect);
+  __setPrimaryHttpRunnerForTests(run);
 
   return {
     calls,
+    run,
     async dispose() {
       __setPrimaryHttpRunnerForTests();
       await runtime.dispose();