diff --git a/code/lib/core-server/src/build-dev.ts b/code/lib/core-server/src/build-dev.ts
index 7db1da14ca1..b7a808babc1 100644
--- a/code/lib/core-server/src/build-dev.ts
+++ b/code/lib/core-server/src/build-dev.ts
@@ -36,7 +36,7 @@ export async function buildDevStandalone(options: CLIOptions & LoadOptions & Bui
     getServerPort(options.port),
     versionUpdates
       ? updateCheck(version)
-      : Promise.resolve({ success: false, data: {}, time: Date.now() }),
+      : Promise.resolve({ success: false, cached: false, data: {}, time: Date.now() }),
     releaseNotes
       ? getReleaseNotesData(version, cache)
       : Promise.resolve(getReleaseNotesFailedState(version)),
diff --git a/code/lib/core-server/src/dev-server.ts b/code/lib/core-server/src/dev-server.ts
index b3023f4d422..f25c87e46d2 100644
--- a/code/lib/core-server/src/dev-server.ts
+++ b/code/lib/core-server/src/dev-server.ts
@@ -1,7 +1,13 @@
 import express, { Router } from 'express';
 import compression from 'compression';
 
-import type { CoreConfig, DocsOptions, Options, StorybookConfig } from '@storybook/types';
+import type {
+  CoreConfig,
+  DocsOptions,
+  Options,
+  StorybookConfig,
+  VersionCheck,
+} from '@storybook/types';
 
 import { normalizeStories, logConfig } from '@storybook/core-common';
 
@@ -24,6 +30,12 @@ export const router: Router = new Router();
 
 export const DEBOUNCE = 100;
 
+const versionStatus = (versionCheck: VersionCheck) => {
+  if (versionCheck.error) return 'error';
+  if (versionCheck.cached) return 'cached';
+  return 'success';
+};
+
 export async function storybookDevServer(options: Options) {
   const startTime = process.hrtime();
   const app = express();
@@ -67,8 +79,10 @@ export async function storybookDevServer(options: Options) {
   if (!core?.disableTelemetry) {
     initializedStoryIndexGenerator.then(async (generator) => {
       const storyIndex = await generator?.getIndex();
+      const { versionCheck, versionUpdates } = options;
       const payload = storyIndex
         ? {
+            versionStatus: versionUpdates ? versionStatus(versionCheck) : 'disabled',
             storyIndex: summarizeIndex(storyIndex),
           }
         : undefined;
diff --git a/code/lib/core-server/src/utils/update-check.ts b/code/lib/core-server/src/utils/update-check.ts
index b20881d1235..f4c463d2e34 100644
--- a/code/lib/core-server/src/utils/update-check.ts
+++ b/code/lib/core-server/src/utils/update-check.ts
@@ -22,13 +22,13 @@ export const updateCheck = async (version: string): Promise<VersionCheck> => {
         new Promise((res, rej) => global.setTimeout(rej, 1500)),
       ]);
       const data = await fromFetch.json();
-      result = { success: true, data, time };
+      result = { success: true, cached: false, data, time };
       await cache.set('lastUpdateCheck', result);
     } else {
-      result = fromCache;
+      result = { ...fromCache, cached: true };
     }
   } catch (error) {
-    result = { success: false, error, time };
+    result = { success: false, cached: false, error, time };
   }
   return result;
 };
diff --git a/code/lib/types/src/modules/core-common.ts b/code/lib/types/src/modules/core-common.ts
index d306fa13cb2..1732dcc749d 100644
--- a/code/lib/types/src/modules/core-common.ts
+++ b/code/lib/types/src/modules/core-common.ts
@@ -94,6 +94,7 @@ export interface Ref {
 
 export interface VersionCheck {
   success: boolean;
+  cached: boolean;
   data?: any;
   error?: any;
   time: number;