diff --git a/config.sample.js b/config.sample.js
index c5a9d15..44d888c 100644
--- a/config.sample.js
+++ b/config.sample.js
@@ -61,6 +61,13 @@ module.exports = {
 		// The length of the random generated name for the uploaded files
 		fileLength: 32,
 
+		/*
+			This option will limit how many times it will try to generate random names
+			for uploaded files. If this value is higher than 1, it will help in cases
+			where files with the same name already exists (higher chance with shorter file name length).
+		*/
+		maxTries: 1,
+
 		/*
 			NOTE: Thumbnails are only for the admin panel and they require you
 			to install a separate binary called graphicsmagick (http://www.graphicsmagick.org)
diff --git a/controllers/uploadController.js b/controllers/uploadController.js
index 4e4b2e0..51c0cf4 100644
--- a/controllers/uploadController.js
+++ b/controllers/uploadController.js
@@ -9,12 +9,25 @@ const utils = require('./utilsController.js');
 
 const uploadsController = {};
 
+// Let's default it to only 1 try
+const maxTries = config.uploads.maxTries || 1;
+const uploadDir = path.join(__dirname, '..', config.uploads.folder);
+
 const storage = multer.diskStorage({
 	destination: function(req, file, cb) {
-		cb(null, path.join(__dirname, '..', config.uploads.folder));
+		cb(null, uploadDir);
 	},
-	filename: function(req, file, cb) {
-		cb(null, randomstring.generate(config.uploads.fileLength) + path.extname(file.originalname));
+  	filename: function(req, file, cb) {
+		const access = i => {
+			const name = randomstring.generate(config.uploads.fileLength) + path.extname(file.originalname);
+			fs.access(path.join(uploadDir, name), err => {
+				if (err) return cb(null, name);
+				console.log(`A file named "${name}" already exists (${++i}/${maxTries}).`);
+				if (i < maxTries) return access(i);
+				return cb('Could not allocate a unique file name. Try again?');
+			});
+		};
+		access(0);
 	}
 });