diff --git a/src/lib/server/s3.ts b/src/lib/server/s3.ts
index b9ca7b3..5f50a7c 100644
--- a/src/lib/server/s3.ts
+++ b/src/lib/server/s3.ts
@@ -1,5 +1,6 @@
 import {
   CreateBucketCommand,
+  DeleteObjectCommand,
   HeadBucketCommand,
   PutBucketPolicyCommand,
   PutObjectCommand,
@@ -119,3 +120,20 @@ export const uploadObject = async (
     throw error;
   }
 };
+
+export const deleteObject = async (bucketName: string, fileName: string) => {
+  const deleteObjectCommand = new DeleteObjectCommand({
+    Bucket: bucketName,
+    Key: fileName,
+  });
+
+  try {
+    await s3Client.send(deleteObjectCommand);
+  } catch (error) {
+    console.error(
+      `Error uploading file ${fileName} to bucket ${bucketName}:`,
+      error
+    );
+    throw error;
+  }
+};
diff --git a/src/routes/api/upload/+server.ts b/src/routes/api/upload/+server.ts
index 09d40ca..4b685a0 100644
--- a/src/routes/api/upload/+server.ts
+++ b/src/routes/api/upload/+server.ts
@@ -1,6 +1,6 @@
 // src/routes/api/upload.js
 
-import { ensureBucketExists, uploadObject } from "$lib/server/s3";
+import { deleteObject, ensureBucketExists, uploadObject } from "$lib/server/s3";
 import type { RequestEvent } from "@sveltejs/kit";
 import { generateId } from "lucia";
 
@@ -8,7 +8,7 @@ export async function POST(event: RequestEvent): Promise<Response> {
   try {
     const contentType = event.request.headers.get("content-type") ?? "";
     const fileExtension = contentType.split("/").pop();
-    const fileName = `${generateId(25)}.${fileExtension}`;
+    const fileName = `${generateId(50)}.${fileExtension}`;
     const bucket = event.request.headers.get("bucket") as string;
 
     if (!fileExtension || !fileName) {
@@ -49,6 +49,11 @@ export async function POST(event: RequestEvent): Promise<Response> {
 
     await ensureBucketExists(bucket);
 
+    if (event.locals.user?.icon) {
+      const key: string = event.locals.user.icon.split("/").pop() as string;
+      await deleteObject(bucket, key);
+    }
+
     const objectUrl = await uploadObject(
       bucket,
       fileName,