diff --git a/x-pack/plugins/security_solution/server/integration_tests/lib/helpers.ts b/x-pack/plugins/security_solution/server/integration_tests/lib/helpers.ts
index 4cf1b69e0873ae..ccc73435636e96 100644
--- a/x-pack/plugins/security_solution/server/integration_tests/lib/helpers.ts
+++ b/x-pack/plugins/security_solution/server/integration_tests/lib/helpers.ts
@@ -22,8 +22,8 @@ const asyncUnlink = Util.promisify(Fs.unlink);
  */
 export async function eventually<T>(
   cb: () => Promise<T>,
-  duration: number = 60000,
-  interval: number = 1000
+  duration: number = 120000,
+  interval: number = 3000
 ) {
   let elapsed = 0;
 
diff --git a/x-pack/plugins/security_solution/server/integration_tests/telemetry.test.ts b/x-pack/plugins/security_solution/server/integration_tests/telemetry.test.ts
index 36284722cbf592..50d2d5e5cd6499 100644
--- a/x-pack/plugins/security_solution/server/integration_tests/telemetry.test.ts
+++ b/x-pack/plugins/security_solution/server/integration_tests/telemetry.test.ts
@@ -148,8 +148,7 @@ describe('telemetry tasks', () => {
     });
   });
 
-  // FLAKY: https://github.com/elastic/kibana/issues/187719
-  describe.skip('detection-rules', () => {
+  describe('detection-rules', () => {
     it('should execute when scheduled', async () => {
       await mockAndScheduleDetectionRulesTask();
 
@@ -263,7 +262,7 @@ describe('telemetry tasks', () => {
       // wait until the events are sent to the telemetry server
       const body = await eventually(async () => {
         const found = mockedAxiosPost.mock.calls.find(([url]) => {
-          return url.startsWith(ENDPOINT_STAGING) && url.endsWith('alerts-endpoint');
+          return url.startsWith(ENDPOINT_STAGING) && url.endsWith(TelemetryChannel.ENDPOINT_ALERTS);
         });
 
         expect(found).not.toBeFalsy();
@@ -274,6 +273,25 @@ describe('telemetry tasks', () => {
       expect(body).not.toBeFalsy();
       expect(body.Endpoint).not.toBeFalsy();
     });
+
+    it('should execute get license info', async () => {
+      await mockAndScheduleEndpointDiagnosticsTask();
+
+      // wait until the events are sent to the telemetry server
+      const body = await eventually(async () => {
+        const found = mockedAxiosPost.mock.calls.find(([url]) => {
+          return url.startsWith(ENDPOINT_STAGING) && url.endsWith(TelemetryChannel.ENDPOINT_ALERTS);
+        });
+
+        expect(found).not.toBeFalsy();
+
+        return JSON.parse((found ? found[1] : '{}') as string);
+      });
+
+      expect(body).not.toBeFalsy();
+      expect(body.license).not.toBeFalsy();
+      expect(body.license.status).not.toBeFalsy();
+    });
   });
 
   describe('endpoint-meta-telemetry', () => {
@@ -680,8 +698,7 @@ describe('telemetry tasks', () => {
       expect(body.file).toStrictEqual(alertsDetectionsRequest.file);
     });
 
-    // Flaky: https://github.com/elastic/kibana/issues/188234
-    it.skip('should manage runtime errors searching endpoint metrics', async () => {
+    it('should manage runtime errors searching endpoint metrics', async () => {
       const errorMessage = 'Something went wront';
 
       async function* mockedGenerator(
diff --git a/x-pack/plugins/security_solution/server/lib/telemetry/async_sender.ts b/x-pack/plugins/security_solution/server/lib/telemetry/async_sender.ts
index 07e098b1cc979e..6c2def2abb61d9 100644
--- a/x-pack/plugins/security_solution/server/lib/telemetry/async_sender.ts
+++ b/x-pack/plugins/security_solution/server/lib/telemetry/async_sender.ts
@@ -21,7 +21,7 @@ import { TelemetryChannel, TelemetryCounter } from './types';
 import * as collections from './collections_helpers';
 import { CachedSubject, retryOnError$ } from './rxjs_helpers';
 import { SenderUtils } from './sender_helpers';
-import { newTelemetryLogger } from './helpers';
+import { copyLicenseFields, newTelemetryLogger } from './helpers';
 import { type TelemetryLogger } from './telemetry_logger';
 
 export const DEFAULT_QUEUE_CONFIG: QueueConfig = {
@@ -291,6 +291,14 @@ export class AsyncTelemetryEventsSender implements IAsyncTelemetryEventsSender {
         };
       }
 
+      if (event.channel === TelemetryChannel.ENDPOINT_ALERTS) {
+        const licenseInfo = this.telemetryReceiver?.getLicenseInfo();
+        additional = {
+          ...additional,
+          ...(licenseInfo ? { license: copyLicenseFields(licenseInfo) } : {}),
+        };
+      }
+
       event.payload = {
         ...event.payload,
         ...additional,
diff --git a/x-pack/plugins/security_solution/server/lib/telemetry/receiver.ts b/x-pack/plugins/security_solution/server/lib/telemetry/receiver.ts
index ebff5655d99e03..22f85d19c83d86 100644
--- a/x-pack/plugins/security_solution/server/lib/telemetry/receiver.ts
+++ b/x-pack/plugins/security_solution/server/lib/telemetry/receiver.ts
@@ -102,6 +102,8 @@ export interface ITelemetryReceiver {
 
   fetchClusterInfo(): Promise<ESClusterInfo>;
 
+  getLicenseInfo(): Nullable<ESLicense>;
+
   fetchLicenseInfo(): Promise<Nullable<ESLicense>>;
 
   closePointInTime(pitId: string): Promise<void>;
@@ -248,6 +250,7 @@ export class TelemetryReceiver implements ITelemetryReceiver {
   private getIndexForType?: (type: string) => string;
   private alertsIndex?: string;
   private clusterInfo?: ESClusterInfo;
+  private licenseInfo?: Nullable<ESLicense>;
   private processTreeFetcher?: Fetcher;
   private packageService?: PackageService;
   private experimentalFeatures: ExperimentalFeatures | undefined;
@@ -280,6 +283,7 @@ export class TelemetryReceiver implements ITelemetryReceiver {
     this.soClient =
       core?.savedObjects.createInternalRepository() as unknown as SavedObjectsClientContract;
     this.clusterInfo = await this.fetchClusterInfo();
+    this.licenseInfo = await this.fetchLicenseInfo();
     this.experimentalFeatures = endpointContextService?.experimentalFeatures;
     const elasticsearch = core?.elasticsearch.client as unknown as IScopedClusterClient;
     this.processTreeFetcher = new Fetcher(elasticsearch);
@@ -291,6 +295,10 @@ export class TelemetryReceiver implements ITelemetryReceiver {
     return this.clusterInfo;
   }
 
+  public getLicenseInfo(): Nullable<ESLicense> {
+    return this.licenseInfo;
+  }
+
   public getAlertsIndex(): string | undefined {
     return this.alertsIndex;
   }
diff --git a/x-pack/plugins/security_solution/server/lib/telemetry/tasks/diagnostic.ts b/x-pack/plugins/security_solution/server/lib/telemetry/tasks/diagnostic.ts
index 8148a81e8f915f..a6825a7517b4f4 100644
--- a/x-pack/plugins/security_solution/server/lib/telemetry/tasks/diagnostic.ts
+++ b/x-pack/plugins/security_solution/server/lib/telemetry/tasks/diagnostic.ts
@@ -8,11 +8,10 @@
 import type { Logger } from '@kbn/core/server';
 import { newTelemetryLogger, getPreviousDiagTaskTimestamp } from '../helpers';
 import type { ITelemetryEventsSender } from '../sender';
-import type { TelemetryEvent } from '../types';
+import { TelemetryChannel, type TelemetryEvent } from '../types';
 import type { ITelemetryReceiver } from '../receiver';
 import type { TaskExecutionPeriod } from '../task';
 import type { ITaskMetricsService } from '../task_metrics.types';
-import { TELEMETRY_CHANNEL_ENDPOINT_ALERTS } from '../constants';
 import { copyAllowlistedFields, filterList } from '../filterlists';
 
 export function createTelemetryDiagnosticsTaskConfig() {
@@ -65,7 +64,7 @@ export function createTelemetryDiagnosticsTaskConfig() {
           log.l('Sending diagnostic alerts', {
             alerts_count: alerts.length,
           });
-          await sender.sendOnDemand(TELEMETRY_CHANNEL_ENDPOINT_ALERTS, processedAlerts);
+          sender.sendAsync(TelemetryChannel.ENDPOINT_ALERTS, processedAlerts);
         }
 
         await taskMetricsService.end(trace);