diff --git a/src/filemanager.html b/src/filemanager.html
index 5c049ebc4..e8618117c 100644
--- a/src/filemanager.html
+++ b/src/filemanager.html
@@ -211,7 +211,8 @@
         </div>
         <div class="modal-body">
           <div ng-show="uploadStatus.error">
-            <p class="text-danger">{{ uploadStatus.error }}</p>
+            <p class="text-danger" ng-show="uploadStatus.error === 'exists'">One or more files already exist.</p>
+            <p class="text-danger" ng-show="uploadStatus.error === 'generic'">Failed to upload one or more files. Please try again.</p>
           </div>
           <div class="progress progress-striped active" ng-hide="uploadStatus.error">
             <div class="progress-bar progress-bar-success" role="progressbar" style="width: {{ uploadStatus.percentDone || 0 }}%"></div>
@@ -220,7 +221,9 @@
         </div>
         <div class="modal-footer" style="text-align: left;">
           <small ng-hide="uploadStatus.error">Do not refresh the page until upload has finished.</small>
-          <button class="btn btn-primary pull-right" ng-show="uploadStatus.error" data-dismiss="modal">Close</button>
+          <button class="btn btn-default pull-right" ng-show="uploadStatus.error" data-dismiss="modal">Close</button>
+          <button class="btn btn-primary pull-right" ng-show="uploadStatus.error === 'generic'" ng-click="retryUpload(false)">Retry</button>
+          <button class="btn btn-danger pull-right" ng-show="uploadStatus.error === 'exists'" ng-click="retryUpload(true)">Overwrite</button>
         </div>
       </div>
     </div>
diff --git a/src/js/client.js b/src/js/client.js
index e5a18d88f..9cee23a57 100644
--- a/src/js/client.js
+++ b/src/js/client.js
@@ -2630,10 +2630,12 @@ angular.module('Application').service('Client', ['$http', '$interval', '$timeout
         });
     };
 
-    Client.prototype.filesUpload = function (appId, path, file, progressHandler, callback) {
+    Client.prototype.filesUpload = function (appId, path, file, overwrite, progressHandler, callback) {
         var fd = new FormData();
         fd.append('file', file);
 
+        if (overwrite) fd.append('overwrite', 'true');
+
         function done(error, data, status) {
             if (error) return callback(error);
             if (status !== 200) return callback(new ClientError(status, data));
diff --git a/src/js/filemanager.js b/src/js/filemanager.js
index 26415f7c9..ae30723ee 100644
--- a/src/js/filemanager.js
+++ b/src/js/filemanager.js
@@ -216,9 +216,9 @@ app.controller('FileManagerController', ['$scope', '$timeout', 'Client', functio
         var folderItem;
         try {
             folderItem = event.originalEvent.dataTransfer.items[0].webkitGetAsEntry();
-            if (folderItem.isFile) return uploadFiles(event.originalEvent.dataTransfer.files, targetFolder);
+            if (folderItem.isFile) return uploadFiles(event.originalEvent.dataTransfer.files, targetFolder, false);
         } catch (e) {
-            return uploadFiles(event.originalEvent.dataTransfer.files, targetFolder);
+            return uploadFiles(event.originalEvent.dataTransfer.files, targetFolder, false);
         }
 
         // if we got here we have a folder drop and a modern browser
@@ -252,7 +252,7 @@ app.controller('FileManagerController', ['$scope', '$timeout', 'Client', functio
 
             if (error) return console.error(error);
 
-            uploadFiles(fileList, targetFolder);
+            uploadFiles(fileList, targetFolder, false);
         });
     };
 
@@ -332,13 +332,16 @@ app.controller('FileManagerController', ['$scope', '$timeout', 'Client', functio
         countDone: 0,
         size: 0,
         done: 0,
-        percentDone: 0
+        percentDone: 0,
+        files: [],
+        targetFolder: ''
     };
 
-    function uploadFiles(files, targetFolder) {
+    function uploadFiles(files, targetFolder, overwrite) {
         if (!files || !files.length) return;
 
         targetFolder = targetFolder || '';
+        overwrite = !!overwrite;
 
         // prevent it from getting closed
         $('#uploadModal').modal({
@@ -346,6 +349,8 @@ app.controller('FileManagerController', ['$scope', '$timeout', 'Client', functio
             keyboard: false
         });
 
+        $scope.uploadStatus.files = files;
+        $scope.uploadStatus.targetFolder = targetFolder;
         $scope.uploadStatus.error = null;
         $scope.uploadStatus.busy = true;
         $scope.uploadStatus.count = files.length;
@@ -363,7 +368,7 @@ app.controller('FileManagerController', ['$scope', '$timeout', 'Client', functio
 
             $scope.uploadStatus.fileName = file.name;
 
-            Client.filesUpload($scope.appId, filePath, file, function (loaded) {
+            Client.filesUpload($scope.appId, filePath, file, overwrite, function (loaded) {
                 $scope.uploadStatus.percentDone = ($scope.uploadStatus.done+loaded) * 100 / $scope.uploadStatus.size;
             }, function (error) {
                 if (error) return callback(error);
@@ -377,9 +382,12 @@ app.controller('FileManagerController', ['$scope', '$timeout', 'Client', functio
         }, function (error) {
             $scope.uploadStatus.busy = false;
 
-            if (error) {
+            if (error && error.statusCode === 409) {
+                $scope.uploadStatus.error = 'exists';
+                return;
+            } else if (error) {
                 console.error(error);
-                $scope.uploadStatus.error = 'Failed to upload one or more files. Please try again.';
+                $scope.uploadStatus.error = 'generic';
                 return;
             }
 
@@ -390,17 +398,23 @@ app.controller('FileManagerController', ['$scope', '$timeout', 'Client', functio
             $scope.uploadStatus.size = 0;
             $scope.uploadStatus.done = 0;
             $scope.uploadStatus.percentDone = 100;
+            $scope.uploadStatus.files = [];
+            $scope.uploadStatus.targetFolder = '';
 
             $scope.refresh();
         });
     }
 
+    $scope.retryUpload = function (overwrite) {
+        uploadFiles($scope.uploadStatus.files, $scope.uploadStatus.targetFolder, !!overwrite);
+    };
+
     // file upload
-    $('#uploadFileInput').on('change', function (e) { uploadFiles(e.target.files || []); });
+    $('#uploadFileInput').on('change', function (e) { uploadFiles(e.target.files || [], '', false); });
     $scope.onUploadFile = function () { $('#uploadFileInput').click(); };
 
     // folder upload
-    $('#uploadFolderInput').on('change', function (e ) { uploadFiles(e.target.files || []); });
+    $('#uploadFolderInput').on('change', function (e ) { uploadFiles(e.target.files || [], '', false); });
     $scope.onUploadFolder = function () { $('#uploadFolderInput').click(); };
 
     $scope.newDirectory = {
@@ -459,7 +473,7 @@ app.controller('FileManagerController', ['$scope', '$timeout', 'Client', functio
 
             var filePath = sanitize($scope.cwd + '/' + $scope.newFile.name);
 
-            Client.filesUpload($scope.appId, filePath, new File([], $scope.newFile.name), function () {}, function (error) {
+            Client.filesUpload($scope.appId, filePath, new File([], $scope.newFile.name), false, function () {}, function (error) {
                 $scope.newFile.busy = false;
                 if (error && error.statusCode === 409) return $scope.newFile.error = 'Already exists';
                 if (error) return Client.error(error);
@@ -569,7 +583,7 @@ app.controller('FileManagerController', ['$scope', '$timeout', 'Client', functio
             var filePath = sanitize($scope.cwd + '/' + $scope.textEditor.entry.fileName);
             var file = new File([newContent], 'file');
 
-            Client.filesUpload($scope.appId, filePath, file, function () {}, function (error) {
+            Client.filesUpload($scope.appId, filePath, file, true, function () {}, function (error) {
                 if (error) return Client.error(error);
 
                 $timeout(function () {