diff --git a/src/http/bootstrap.ts b/src/http/bootstrap.ts
index 814c445..d7ad7fc 100644
--- a/src/http/bootstrap.ts
+++ b/src/http/bootstrap.ts
@@ -9,22 +9,20 @@ import { MaintenanceService } from '../services/maintenance';
 export async function startServices(_db: Database): Promise<void> {
   // Exponer la DB globalmente vía locator para servicios que lo usen.
   try { setDb(_db); } catch {}
-  await WebhookManager.registerWebhook();
-  // Add small delay to allow webhook to propagate
-  await new Promise(resolve => setTimeout(resolve, 1000));
-  const isActive = await WebhookManager.verifyWebhook();
-  if (!isActive) {
-    console.error('❌ Webhook verification failed - retrying in 2 seconds...');
-    await new Promise(resolve => setTimeout(resolve, 2000));
-    const isActiveRetry = await WebhookManager.verifyWebhook();
-    if (!isActiveRetry) {
-      console.error('❌ Webhook verification failed after retry');
-      process.exit(1);
-    }
+
+  // Iniciar aseguramiento automático del webhook en background (reintentos con backoff)
+  try {
+    WebhookManager.startAutoEnsure();
+  } catch (e) {
+    console.error('⚠️ Failed to start webhook auto-ensure loop:', e);
   }
 
-  // Initialize groups - critical for operation
-  await GroupSyncService.checkInitialGroups();
+  // Initialize groups - critical for operation (no abortar si falla)
+  try {
+    await GroupSyncService.checkInitialGroups();
+  } catch (e) {
+    console.error('⚠️ Initial groups check failed (will rely on schedulers to recover):', e);
+  }
 
   // Start groups scheduler (periodic sync of groups)
   try {
@@ -73,6 +71,9 @@ export async function startServices(_db: Database): Promise<void> {
 }
 
 export function stopServices(): void {
+  try {
+    WebhookManager.stopAutoEnsure();
+  } catch {}
   try {
     ResponseQueue.stopCleanupScheduler();
   } catch {}
diff --git a/tests/unit/services/webhook-manager.test.ts b/tests/unit/services/webhook-manager.test.ts
index ae23d2d..e88351f 100644
--- a/tests/unit/services/webhook-manager.test.ts
+++ b/tests/unit/services/webhook-manager.test.ts
@@ -80,4 +80,74 @@ describe('WebhookManager', () => {
       }
     }).toThrow();
   });
+
+  test('should retry registration in background until success', async () => {
+    // Acelerar reintentos
+    process.env.WEBHOOK_RETRY_INITIAL_DELAY_MS = '10';
+    process.env.WEBHOOK_RETRY_MAX_DELAY_MS = '20';
+    process.env.WEBHOOK_RETRY_DEGRADED_INTERVAL_MS = '50';
+
+    const originalFetch: any = globalThis.fetch;
+    let setCalls = 0;
+
+    const fetchSpy = mock(async (input: any, init?: any) => {
+      const url = typeof input === 'string' ? input : input.url;
+
+      // Self-test of our own webhook endpoint
+      if (url === process.env.WEBHOOK_URL) {
+        return new Response('ok', { status: 200, headers: { 'Content-Type': 'application/json' } });
+      }
+
+      // Register webhook endpoint (first fails, then succeeds)
+      if (typeof url === 'string' && url.includes('/webhook/set/')) {
+        setCalls++;
+        if (setCalls < 2) {
+          return new Response('unavailable', { status: 503, statusText: 'Service Unavailable' });
+        }
+        const body = JSON.stringify({
+          id: 'test-id',
+          url: process.env.WEBHOOK_URL,
+          enabled: true,
+          events: ['APPLICATION_STARTUP']
+        });
+        return new Response(body, { status: 200, headers: { 'Content-Type': 'application/json' } });
+      }
+
+      // Verify webhook endpoint (returns enabled)
+      if (typeof url === 'string' && url.includes('/webhook/find/')) {
+        const body = JSON.stringify({
+          enabled: true,
+          url: process.env.WEBHOOK_URL,
+          events: ['APPLICATION_STARTUP']
+        });
+        return new Response(body, { status: 200, headers: { 'Content-Type': 'application/json' } });
+      }
+
+      return new Response('not found', { status: 404 });
+    });
+
+    // @ts-ignore
+    globalThis.fetch = fetchSpy;
+
+    try {
+      // Asegurar que no haya un lazo previo corriendo
+      try { (WebhookManager as any).stopAutoEnsure(); } catch {}
+
+      WebhookManager['startAutoEnsure']();
+
+      // Esperar a que el lazo logre activar el webhook (o agote timeout)
+      const deadline = Date.now() + 2000;
+      while (WebhookManager['autoEnsureActive'] && Date.now() < deadline) {
+        await new Promise(res => setTimeout(res, 20));
+      }
+
+      expect(WebhookManager['autoEnsureActive']).toBe(false);
+      expect(fetchSpy).toHaveBeenCalled();
+      expect(setCalls).toBeGreaterThan(1);
+    } finally {
+      try { WebhookManager['stopAutoEnsure'](); } catch {}
+      // @ts-ignore
+      globalThis.fetch = originalFetch;
+    }
+  });
 });