diff --git a/server/api/plextv.ts b/server/api/plextv.ts
index 1d474ac40..2fc4523a8 100644
--- a/server/api/plextv.ts
+++ b/server/api/plextv.ts
@@ -2,6 +2,7 @@ import type { PlexDevice } from '@server/interfaces/api/plexInterfaces';
 import cacheManager from '@server/lib/cache';
 import { getSettings } from '@server/lib/settings';
 import logger from '@server/logger';
+import { randomUUID } from 'node:crypto';
 import xml2js from 'xml2js';
 import ExternalAPI from './externalapi';
 
@@ -363,6 +364,24 @@ class PlexTvAPI extends ExternalAPI {
       };
     }
   }
+
+  public async pingToken() {
+    try {
+      const response = await this.axios.get('/api/v2/ping', {
+        headers: {
+          'X-Plex-Client-Identifier': randomUUID(),
+        },
+      });
+      if (!response?.data?.pong) {
+        throw new Error('No pong response');
+      }
+    } catch (e) {
+      logger.error('Failed to ping token', {
+        label: 'Plex Refresh Token',
+        errorMessage: e.message,
+      });
+    }
+  }
 }
 
 export default PlexTvAPI;
diff --git a/server/job/schedule.ts b/server/job/schedule.ts
index fea1f53d0..bc693dd9b 100644
--- a/server/job/schedule.ts
+++ b/server/job/schedule.ts
@@ -1,6 +1,7 @@
 import availabilitySync from '@server/lib/availabilitySync';
 import downloadTracker from '@server/lib/downloadtracker';
 import ImageProxy from '@server/lib/imageproxy';
+import refreshToken from '@server/lib/refreshToken';
 import { plexFullScanner, plexRecentScanner } from '@server/lib/scanners/plex';
 import { radarrScanner } from '@server/lib/scanners/radarr';
 import { sonarrScanner } from '@server/lib/scanners/sonarr';
@@ -168,5 +169,19 @@ export const startJobs = (): void => {
     }),
   });
 
+  scheduledJobs.push({
+    id: 'plex-refresh-token',
+    name: 'Plex Refresh Token',
+    type: 'process',
+    interval: 'fixed',
+    cronSchedule: jobs['plex-refresh-token'].schedule,
+    job: schedule.scheduleJob(jobs['plex-refresh-token'].schedule, () => {
+      logger.info('Starting scheduled job: Plex Refresh Token', {
+        label: 'Jobs',
+      });
+      refreshToken.run();
+    }),
+  });
+
   logger.info('Scheduled jobs loaded', { label: 'Jobs' });
 };
diff --git a/server/lib/refreshToken.ts b/server/lib/refreshToken.ts
new file mode 100644
index 000000000..ac7bd3463
--- /dev/null
+++ b/server/lib/refreshToken.ts
@@ -0,0 +1,37 @@
+import PlexTvAPI from '@server/api/plextv';
+import { getRepository } from '@server/datasource';
+import { User } from '@server/entity/User';
+import logger from '@server/logger';
+
+class RefreshToken {
+  public async run() {
+    const userRepository = getRepository(User);
+
+    const users = await userRepository
+      .createQueryBuilder('user')
+      .addSelect('user.plexToken')
+      .where("user.plexToken != ''")
+      .getMany();
+
+    for (const user of users) {
+      await this.refreshUserToken(user);
+    }
+  }
+
+  private async refreshUserToken(user: User) {
+    if (!user.plexToken) {
+      logger.warn('Skipping user refresh token for user without plex token', {
+        label: 'Plex Refresh Token',
+        user: user.displayName,
+      });
+      return;
+    }
+
+    const plexTvApi = new PlexTvAPI(user.plexToken);
+    plexTvApi.pingToken();
+  }
+}
+
+const refreshToken = new RefreshToken();
+
+export default refreshToken;
diff --git a/server/lib/settings.ts b/server/lib/settings.ts
index 6602f3104..63daf17f3 100644
--- a/server/lib/settings.ts
+++ b/server/lib/settings.ts
@@ -248,6 +248,7 @@ export type JobId =
   | 'plex-recently-added-scan'
   | 'plex-full-scan'
   | 'plex-watchlist-sync'
+  | 'plex-refresh-token'
   | 'radarr-scan'
   | 'sonarr-scan'
   | 'download-sync'
@@ -409,6 +410,9 @@ class Settings {
         'plex-watchlist-sync': {
           schedule: '0 */3 * * * *',
         },
+        'plex-refresh-token': {
+          schedule: '0 0 5 * * *',
+        },
         'radarr-scan': {
           schedule: '0 0 4 * * *',
         },
diff --git a/src/components/Settings/SettingsJobsCache/index.tsx b/src/components/Settings/SettingsJobsCache/index.tsx
index 72bed7c47..ca3edbd14 100644
--- a/src/components/Settings/SettingsJobsCache/index.tsx
+++ b/src/components/Settings/SettingsJobsCache/index.tsx
@@ -53,6 +53,7 @@ const messages: { [messageName: string]: MessageDescriptor } = defineMessages({
   'plex-recently-added-scan': 'Plex Recently Added Scan',
   'plex-full-scan': 'Plex Full Library Scan',
   'plex-watchlist-sync': 'Plex Watchlist Sync',
+  'plex-refresh-token': 'Plex Refresh Token',
   'availability-sync': 'Media Availability Sync',
   'radarr-scan': 'Radarr Scan',
   'sonarr-scan': 'Sonarr Scan',
diff --git a/src/i18n/locale/en.json b/src/i18n/locale/en.json
index 10165c9e1..60a2d46bc 100644
--- a/src/i18n/locale/en.json
+++ b/src/i18n/locale/en.json
@@ -768,6 +768,7 @@
   "components.Settings.SettingsJobsCache.nextexecution": "Next Execution",
   "components.Settings.SettingsJobsCache.plex-full-scan": "Plex Full Library Scan",
   "components.Settings.SettingsJobsCache.plex-recently-added-scan": "Plex Recently Added Scan",
+  "components.Settings.SettingsJobsCache.plex-refresh-token": "Plex Refresh Token",
   "components.Settings.SettingsJobsCache.plex-watchlist-sync": "Plex Watchlist Sync",
   "components.Settings.SettingsJobsCache.process": "Process",
   "components.Settings.SettingsJobsCache.radarr-scan": "Radarr Scan",