diff --git a/apps/desktop/src/App.vue b/apps/desktop/src/App.vue
index 99a7e980b5..a4b58c11cc 100644
--- a/apps/desktop/src/App.vue
+++ b/apps/desktop/src/App.vue
@@ -39,7 +39,7 @@ import { useExternalSqlFileChanges } from "@/composables/useExternalSqlFileChang
 import { useWebDavAutoUpload } from "@/composables/useWebDavAutoUpload";
 import { useScheduledDatabaseBackups } from "@/composables/useScheduledDatabaseBackups";
 import { shouldDrawDesktopWindowFrame } from "@/composables/useWindowControls";
-import { createOpenTabsRestorationBarrier, initializeDesktopOpenTabs, type OpenTabsRestorationBarrier } from "@/lib/app/openTabsStartup";
+import { createOpenTabsRestorationBarrier, initializeDesktopOpenTabs, initializeOpenTabs, type OpenTabsRestorationBarrier } from "@/lib/app/openTabsStartup";
 import { useSaveSqlFolderSelection } from "@/composables/useSaveSqlFolderSelection";
 import "@/i18n";
 import { translateBackendError } from "@/i18n/backend-errors";
@@ -2376,7 +2376,6 @@ async function initApp() {
     console.log(`[STARTUP]   queryStore.initOpenTabs: ${(performance.now() - t0).toFixed(0)}ms`);
   };
 
-  if (!desktopOpenTabsRestorationBarrier) await settingsStore.initAiConfigs();
   try {
     if (desktopOpenTabsRestorationBarrier) {
       await initializeDesktopOpenTabs({
@@ -2386,7 +2385,11 @@ async function initApp() {
         onOptionalStateError: (error) => console.error("[STARTUP] settingsStore.initAiConfigs failed", error),
       });
     } else {
-      await restoreOpenTabs();
+      await initializeOpenTabs({
+        initializeOptionalState: () => settingsStore.initAiConfigs(),
+        restoreOpenTabs,
+        onOptionalStateError: (error) => console.error("[STARTUP] settingsStore.initAiConfigs failed", error),
+      });
     }
     await settingsStore.initDesktopSettings().catch(() => {});
 
diff --git a/apps/desktop/src/lib/app/openTabsStartup.ts b/apps/desktop/src/lib/app/openTabsStartup.ts
index 4ecd524a42..e41b28b0ed 100644
--- a/apps/desktop/src/lib/app/openTabsStartup.ts
+++ b/apps/desktop/src/lib/app/openTabsStartup.ts
@@ -20,21 +20,28 @@ export function createOpenTabsRestorationBarrier(): OpenTabsRestorationBarrier {
   };
 }
 
-interface InitializeDesktopOpenTabsOptions {
-  barrier: OpenTabsRestorationBarrier;
+interface InitializeOpenTabsOptions {
   initializeOptionalState: () => Promise<void>;
   restoreOpenTabs: () => Promise<void>;
   onOptionalStateError: (error: unknown) => void;
 }
 
-export async function initializeDesktopOpenTabs({ barrier, initializeOptionalState, restoreOpenTabs, onOptionalStateError }: InitializeDesktopOpenTabsOptions): Promise<void> {
+export async function initializeOpenTabs({ initializeOptionalState, restoreOpenTabs, onOptionalStateError }: InitializeOpenTabsOptions): Promise<void> {
   try {
-    try {
-      await initializeOptionalState();
-    } catch (error) {
-      onOptionalStateError(error);
-    }
-    await restoreOpenTabs();
+    await initializeOptionalState();
+  } catch (error) {
+    onOptionalStateError(error);
+  }
+  await restoreOpenTabs();
+}
+
+interface InitializeDesktopOpenTabsOptions extends InitializeOpenTabsOptions {
+  barrier: OpenTabsRestorationBarrier;
+}
+
+export async function initializeDesktopOpenTabs({ barrier, ...options }: InitializeDesktopOpenTabsOptions): Promise<void> {
+  try {
+    await initializeOpenTabs(options);
   } finally {
     barrier.settle();
   }
diff --git a/packages/app-tests/externalSqlFileStartup.test.ts b/packages/app-tests/externalSqlFileStartup.test.ts
index 61777cd6db..7d28460fe0 100644
--- a/packages/app-tests/externalSqlFileStartup.test.ts
+++ b/packages/app-tests/externalSqlFileStartup.test.ts
@@ -1,10 +1,77 @@
 import assert from "node:assert/strict";
 import { readFileSync } from "node:fs";
 import { test } from "vitest";
-import { createOpenTabsRestorationBarrier, initializeDesktopOpenTabs } from "../../apps/desktop/src/lib/app/openTabsStartup.ts";
+import { createOpenTabsRestorationBarrier, initializeDesktopOpenTabs, initializeOpenTabs } from "../../apps/desktop/src/lib/app/openTabsStartup.ts";
 
 const appSource = readFileSync("apps/desktop/src/App.vue", "utf8");
 
+test("web startup reports optional initialization failure and continues restoring persisted state", async () => {
+  const events: string[] = [];
+
+  await initializeOpenTabs({
+    initializeOptionalState: async () => {
+      events.push("initialize-ai-configs");
+      throw new Error("AI config storage unavailable");
+    },
+    restoreOpenTabs: async () => {
+      events.push("initialize-editor-settings");
+      events.push("initialize-connections");
+      events.push("restore-tabs");
+    },
+    onOptionalStateError: () => events.push("report-ai-config-error"),
+  });
+
+  assert.deepEqual(events, ["initialize-ai-configs", "report-ai-config-error", "initialize-editor-settings", "initialize-connections", "restore-tabs"]);
+});
+
+test("shared startup initializes optional state once and propagates required restoration failure", async () => {
+  let optionalInitializationCount = 0;
+
+  await assert.rejects(
+    initializeOpenTabs({
+      initializeOptionalState: async () => {
+        optionalInitializationCount += 1;
+      },
+      restoreOpenTabs: async () => {
+        throw new Error("persisted connections unavailable");
+      },
+      onOptionalStateError: () => assert.fail("successful optional initialization must not be reported"),
+    }),
+    /persisted connections unavailable/,
+  );
+
+  assert.equal(optionalInitializationCount, 1);
+});
+
+test("web startup uses the guarded initializer behind the existing authentication gate", () => {
+  const initAppStart = appSource.indexOf("async function initApp()");
+  const initAppEnd = appSource.indexOf("function restoreActiveConnectionContext", initAppStart);
+  assert.ok(initAppStart >= 0 && initAppEnd > initAppStart);
+
+  const initAppSource = appSource.slice(initAppStart, initAppEnd);
+  const webInitialization = initAppSource.indexOf("await initializeOpenTabs({");
+  const optionalInitialization = initAppSource.indexOf("initializeOptionalState: () => settingsStore.initAiConfigs()", webInitialization);
+  const requiredRestoration = initAppSource.indexOf("restoreOpenTabs,", optionalInitialization);
+  const savedSqlInitialization = initAppSource.indexOf("savedSqlStore.initFromStorage()", requiredRestoration);
+  assert.ok(webInitialization >= 0);
+  assert.ok(optionalInitialization > webInitialization);
+  assert.ok(requiredRestoration > optionalInitialization);
+  assert.ok(savedSqlInitialization > requiredRestoration);
+  assert.equal(initAppSource.includes("if (!desktopOpenTabsRestorationBarrier) await settingsStore.initAiConfigs()"), false);
+
+  const mountedStart = appSource.indexOf("onMounted(async () =>");
+  const mountedEnd = appSource.indexOf("onUnmounted(", mountedStart);
+  assert.ok(mountedStart >= 0 && mountedEnd > mountedStart);
+
+  const mountedSource = appSource.slice(mountedStart, mountedEnd);
+  const authCheck = mountedSource.indexOf('fetch(apiUrl("/api/auth/check"))');
+  const loginRedirect = mountedSource.indexOf('history.replaceState(null, "", webPath("/login"))', authCheck);
+  const authenticatedInitialization = mountedSource.indexOf("if (!setupRequired.value && (!needsAuth.value || authenticated.value)) void initApp()", loginRedirect);
+  assert.ok(authCheck >= 0);
+  assert.ok(loginRedirect > authCheck);
+  assert.ok(authenticatedInitialization > loginRedirect);
+});
+
 test("desktop SQL file opening survives unrelated initialization failure and follows restored tabs", async () => {
   const events: string[] = [];
   const barrier = createOpenTabsRestorationBarrier();