diff --git a/src/routes/upload.ts b/src/routes/upload.ts
index e4a34c3..ed957f7 100644
--- a/src/routes/upload.ts
+++ b/src/routes/upload.ts
@@ -49,6 +49,12 @@ export class UploadRoute extends Route {
                             .toFile(filePath);
                         fileName = `/${dataDirName}/${fileBasename}`;
                         const user = await User.findByPk(req.session.userId);
+                        const oldProfilePicture = path.join(this.dataDir, path.basename(user.profilePicture));
+                        if (await fsx.pathExists(oldProfilePicture)) {
+                            await fsx.unlink(oldProfilePicture);
+                        } else {
+                            globals.logger.warn(`Could not delete ${oldProfilePicture}: Not found!`);
+                        }
                         user.profilePicture = fileName;
                         await user.save();
                         success = true;