diff --git a/srv/app/api/endpoints/users.py b/srv/app/api/endpoints/users.py
index 5e8f347..098c560 100644
--- a/srv/app/api/endpoints/users.py
+++ b/srv/app/api/endpoints/users.py
@@ -1,9 +1,12 @@
 
+import os
+
 from fastapi import Depends, APIRouter, HTTPException, Depends, Request
 from sqlalchemy.orm import Session
 from app.db import models
 from app.core.security import get_current_user
 from app.api import schemas
+from app.core.config import config
 from sqlalchemy import or_, and_, exists
 from sqlalchemy.exc import IntegrityError
 from app.websocket import connection_manager
@@ -19,6 +22,28 @@ def get_db():
         db.close()
 
 
+def _delete_old_avatar_file(file_id: str, db: Session):
+    upload_path = os.path.join('uploads', f"{file_id}.enc")
+    if os.path.exists(upload_path):
+        try:
+            os.remove(upload_path)
+        except OSError:
+            pass
+
+    cloud_item = db.query(models.CloudMediaItem).filter(
+        models.CloudMediaItem.file_id == file_id,
+    ).all()
+    for item in cloud_item:
+        cloud_path = os.path.join(config.CLOUD_MEDIA_CACHE_FOLDER, item.local_filename)
+        if os.path.exists(cloud_path):
+            try:
+                os.remove(cloud_path)
+            except OSError:
+                pass
+        db.delete(item)
+    db.commit()
+
+
 usersRouter = APIRouter(
     prefix="/users",
     tags=[],
@@ -327,6 +352,10 @@ async def update_user_avatar(
     user_to_update = db.merge(current_user)
     avatar_file_id = data.get("avatar_file_id")
     if avatar_file_id:
+        old_avatar_file_id = user_to_update.avatar_file_id
+        if old_avatar_file_id and old_avatar_file_id != avatar_file_id:
+            _delete_old_avatar_file(old_avatar_file_id, db)
+
         user_to_update.avatar_file_id = avatar_file_id
         db.commit()
         print(