diff --git a/server/lib/imageproxy.ts b/server/lib/imageproxy.ts
index 4ea69fcc..3a3098f8 100644
--- a/server/lib/imageproxy.ts
+++ b/server/lib/imageproxy.ts
@@ -171,6 +171,21 @@ class ImageProxy {
     return imageResponse;
   }
 
+  public async clearCachedImage(path: string) {
+    // find cacheKey
+    const cacheKey = this.getCacheKey(path);
+
+    try {
+      const directory = join(this.getCacheDirectory(), cacheKey);
+      await promises.rm(directory, { recursive: true });
+      logger.info(`Cleared ${path} image from cache 'avatar'`, {
+        label: 'Image Cache',
+      });
+    } catch (e) {
+      logger.error(e.message, { label: 'Image Cache' });
+    }
+  }
+
   private async get(cacheKey: string): Promise<ImageResponse | null> {
     try {
       const directory = join(this.getCacheDirectory(), cacheKey);
diff --git a/server/routes/auth.ts b/server/routes/auth.ts
index 6f01135d..a8e239de 100644
--- a/server/routes/auth.ts
+++ b/server/routes/auth.ts
@@ -6,6 +6,7 @@ import { UserType } from '@server/constants/user';
 import { getRepository } from '@server/datasource';
 import { User } from '@server/entity/User';
 import { startJobs } from '@server/job/schedule';
+import ImageProxy from '@server/lib/imageproxy';
 import { Permission } from '@server/lib/permissions';
 import { getSettings } from '@server/lib/settings';
 import logger from '@server/logger';
@@ -376,12 +377,23 @@ authRoutes.post('/jellyfin', async (req, res, next) => {
       );
       // Update the users avatar with their jellyfin profile pic (incase it changed)
       if (account.User.PrimaryImageTag) {
-        user.avatar = `${jellyfinHost}/Users/${account.User.Id}/Images/Primary/?tag=${account.User.PrimaryImageTag}&quality=90`;
+        const avatar = `${jellyfinHost}/Users/${account.User.Id}/Images/Primary/?tag=${account.User.PrimaryImageTag}&quality=90`;
+        if (avatar !== user.avatar) {
+          const avatarProxy = new ImageProxy('avatar', '');
+          avatarProxy.clearCachedImage(user.avatar);
+        }
+        user.avatar = avatar;
       } else {
-        user.avatar = gravatarUrl(user.email || account.User.Name, {
+        const avatar = gravatarUrl(user.email || account.User.Name, {
           default: 'mm',
           size: 200,
         });
+
+        if (avatar !== user.avatar) {
+          const avatarProxy = new ImageProxy('avatar', '');
+          avatarProxy.clearCachedImage(user.avatar);
+        }
+        user.avatar = avatar;
       }
       user.jellyfinUsername = account.User.Name;