diff --git a/src/plugins/telemetry/server/plugin.ts b/src/plugins/telemetry/server/plugin.ts
index 6c8888feafc1f..bd7a2a8c1a8ca 100644
--- a/src/plugins/telemetry/server/plugin.ts
+++ b/src/plugins/telemetry/server/plugin.ts
@@ -89,6 +89,7 @@ export class TelemetryPlugin implements Plugin {
       config$,
       currentKibanaVersion,
       isDev,
+      logger: this.logger,
       router,
       telemetryCollectionManager,
     });
diff --git a/src/plugins/telemetry/server/routes/index.ts b/src/plugins/telemetry/server/routes/index.ts
index ad84cb9d2665d..f46c616a734e0 100644
--- a/src/plugins/telemetry/server/routes/index.ts
+++ b/src/plugins/telemetry/server/routes/index.ts
@@ -18,7 +18,7 @@
  */
 
 import { Observable } from 'rxjs';
-import { IRouter } from 'kibana/server';
+import { IRouter, Logger } from 'kibana/server';
 import { TelemetryCollectionManagerPluginSetup } from 'src/plugins/telemetry_collection_manager/server';
 import { registerTelemetryOptInRoutes } from './telemetry_opt_in';
 import { registerTelemetryUsageStatsRoutes } from './telemetry_usage_stats';
@@ -28,6 +28,7 @@ import { TelemetryConfigType } from '../config';
 
 interface RegisterRoutesParams {
   isDev: boolean;
+  logger: Logger;
   config$: Observable<TelemetryConfigType>;
   currentKibanaVersion: string;
   router: IRouter;
diff --git a/src/plugins/telemetry/server/routes/telemetry_opt_in.ts b/src/plugins/telemetry/server/routes/telemetry_opt_in.ts
index 7dd15f73029e7..aa1de4b2443a4 100644
--- a/src/plugins/telemetry/server/routes/telemetry_opt_in.ts
+++ b/src/plugins/telemetry/server/routes/telemetry_opt_in.ts
@@ -21,7 +21,7 @@ import moment from 'moment';
 import { Observable } from 'rxjs';
 import { take } from 'rxjs/operators';
 import { schema } from '@kbn/config-schema';
-import { IRouter } from 'kibana/server';
+import { IRouter, Logger } from 'kibana/server';
 import {
   StatsGetterConfig,
   TelemetryCollectionManagerPluginSetup,
@@ -39,12 +39,14 @@ import { TelemetryConfigType } from '../config';
 interface RegisterOptInRoutesParams {
   currentKibanaVersion: string;
   router: IRouter;
+  logger: Logger;
   config$: Observable<TelemetryConfigType>;
   telemetryCollectionManager: TelemetryCollectionManagerPluginSetup;
 }
 
 export function registerTelemetryOptInRoutes({
   config$,
+  logger,
   router,
   currentKibanaVersion,
   telemetryCollectionManager,
@@ -95,11 +97,16 @@ export function registerTelemetryOptInRoutes({
 
       if (config.sendUsageFrom === 'server') {
         const optInStatusUrl = config.optInStatusUrl;
-        await sendTelemetryOptInStatus(
+        sendTelemetryOptInStatus(
           telemetryCollectionManager,
           { optInStatusUrl, newOptInStatus },
           statsGetterConfig
-        );
+        ).catch((err) => {
+          // The server is likely behind a firewall and can't reach the remote service
+          logger.warn(
+            `Failed to notify "${optInStatusUrl}" from the server about the opt-in selection. Possibly blocked by a firewall? - Error: ${err.message}`
+          );
+        });
       }
 
       await updateTelemetrySavedObject(context.core.savedObjects.client, attributes);