diff --git a/packages/media-manager/index.ts b/packages/media-manager/index.ts
index 9303980d..c32551a3 100644
--- a/packages/media-manager/index.ts
+++ b/packages/media-manager/index.ts
@@ -10,7 +10,7 @@ export enum MediaBackendType {
 
 interface UploadedFileMetadata {
     uploadedFile: File;
-    path?: string;
+    path: string;
     hash: string;
 }
 
@@ -115,7 +115,7 @@ export class LocalMediaBackend extends MediaBackend {
         const hash = await new MediaHasher().getMediaHash(convertedFile);
 
         const newFile = Bun.file(
-            `${this.config.media.local_uploads_folder}/${hash}`,
+            `${this.config.media.local_uploads_folder}/${hash}/${convertedFile.name}`,
         );
 
         if (await newFile.exists()) {
@@ -126,7 +126,7 @@ export class LocalMediaBackend extends MediaBackend {
 
         return {
             uploadedFile: convertedFile,
-            path: `./uploads/${convertedFile.name}`,
+            path: `${hash}/${convertedFile.name}`,
             hash: hash,
         };
     }
@@ -186,7 +186,7 @@ export class S3MediaBackend extends MediaBackend {
         const hash = await new MediaHasher().getMediaHash(convertedFile);
 
         await this.s3Client.putObject(
-            convertedFile.name,
+            `${hash}/${convertedFile.name}`,
             convertedFile.stream(),
             {
                 size: convertedFile.size,
@@ -195,6 +195,7 @@ export class S3MediaBackend extends MediaBackend {
 
         return {
             uploadedFile: convertedFile,
+            path: `${hash}/${convertedFile.name}`,
             hash: hash,
         };
     }
diff --git a/packages/media-manager/tests/media-backends.test.ts b/packages/media-manager/tests/media-backends.test.ts
index 8b5bfc8c..8f8a758e 100644
--- a/packages/media-manager/tests/media-backends.test.ts
+++ b/packages/media-manager/tests/media-backends.test.ts
@@ -148,7 +148,7 @@ describe("S3MediaBackend", () => {
         expect(result.uploadedFile).toEqual(mockFile);
         expect(result.hash).toHaveLength(64);
         expect(mockS3Client.putObject).toHaveBeenCalledWith(
-            mockFile.name,
+            expect.stringContaining(mockFile.name),
             expect.any(ReadableStream),
             { size: mockFile.size },
         );
@@ -236,7 +236,7 @@ describe("LocalMediaBackend", () => {
         const result = await localMediaBackend.addFile(mockFile);
 
         expect(result.uploadedFile).toEqual(mockFile);
-        expect(result.path).toEqual("./uploads/megamind.png");
+        expect(result.path).toEqual(expect.stringContaining("megamind.png"));
         expect(result.hash).toHaveLength(64);
     });
 
diff --git a/server/api/api/v1/media/index.ts b/server/api/api/v1/media/index.ts
index 8188e5b5..92723578 100644
--- a/server/api/api/v1/media/index.ts
+++ b/server/api/api/v1/media/index.ts
@@ -88,15 +88,19 @@ export default apiRoute<{
                         return;
                     }
 
-                    resolve(
-                        encode(
-                            new Uint8ClampedArray(buffer),
-                            metadata?.width ?? 0,
-                            metadata?.height ?? 0,
-                            4,
-                            4,
-                        ) as string,
-                    );
+                    try {
+                        resolve(
+                            encode(
+                                new Uint8ClampedArray(buffer),
+                                metadata?.width ?? 0,
+                                metadata?.height ?? 0,
+                                4,
+                                4,
+                            ) as string,
+                        );
+                    } catch {
+                        resolve(null);
+                    }
                 }))();
     });
 
@@ -116,16 +120,16 @@ export default apiRoute<{
             throw new Error("Invalid media backend");
     }
 
-    const { uploadedFile } = await mediaManager.addFile(file);
+    const { path } = await mediaManager.addFile(file);
 
-    url = getUrl(uploadedFile.name, config);
+    url = getUrl(path, config);
 
     let thumbnailUrl = "";
 
     if (thumbnail) {
-        const { uploadedFile } = await mediaManager.addFile(thumbnail);
+        const { path } = await mediaManager.addFile(thumbnail);
 
-        thumbnailUrl = getUrl(uploadedFile.name, config);
+        thumbnailUrl = getUrl(path, config);
     }
 
     const newAttachment = await client.attachment.create({
diff --git a/server/api/api/v2/media/index.ts b/server/api/api/v2/media/index.ts
index 6dc3d6ae..dc062d30 100644
--- a/server/api/api/v2/media/index.ts
+++ b/server/api/api/v2/media/index.ts
@@ -88,15 +88,19 @@ export default apiRoute<{
                         return;
                     }
 
-                    resolve(
-                        encode(
-                            new Uint8ClampedArray(buffer),
-                            metadata?.width ?? 0,
-                            metadata?.height ?? 0,
-                            4,
-                            4,
-                        ) as string,
-                    );
+                    try {
+                        resolve(
+                            encode(
+                                new Uint8ClampedArray(buffer),
+                                metadata?.width ?? 0,
+                                metadata?.height ?? 0,
+                                4,
+                                4,
+                            ) as string,
+                        );
+                    } catch {
+                        resolve(null);
+                    }
                 }))();
     });