diff --git a/webroot/rsrc/js/core/DragAndDropFileUpload.js b/webroot/rsrc/js/core/DragAndDropFileUpload.js
--- a/webroot/rsrc/js/core/DragAndDropFileUpload.js
+++ b/webroot/rsrc/js/core/DragAndDropFileUpload.js
@@ -168,6 +168,34 @@
             }
           }));
       }
+
+      var inputField, wipeInputField, handleFileSelect;
+
+      handleFileSelect = JX.bind(this, function (evt) {
+        var files = evt.target.files;
+        for (var i = 0; i < files.length; i++) {
+          this._sendRequest(files[i]);
+        }
+
+        wipeInputField();
+      });
+
+      wipeInputField = JX.bind(this, function () {
+        if(inputField) {
+          inputField.parentNode.removeChild(inputField);
+        }
+
+        inputField = document.createElement('input');
+        inputField.setAttribute('type', 'file');
+        inputField.setAttribute('multiple', 'multiple');
+        inputField.setAttribute('id', 'file-upload-input');
+
+        this._node.parentNode.appendChild(inputField);
+        inputField.addEventListener('change', handleFileSelect, false);
+      });
+
+      wipeInputField();
+      JX.DOM.hide(inputField);
     },
     _sendRequest : function(spec) {
       var file = new JX.PhabricatorFileUpload()
diff --git a/webroot/rsrc/js/core/behavior-phabricator-remarkup-assist.js b/webroot/rsrc/js/core/behavior-phabricator-remarkup-assist.js
--- a/webroot/rsrc/js/core/behavior-phabricator-remarkup-assist.js
+++ b/webroot/rsrc/js/core/behavior-phabricator-remarkup-assist.js
@@ -150,7 +150,7 @@
           .start();
         break;
       case 'fa-cloud-upload':
-        new JX.Workflow('/file/uploaddialog/').start();
+        JX.DOM.show(JX.$('file-upload-input'));
         break;
       case 'fa-arrows-alt':
         if (edit_mode == 'fa-arrows-alt') {