diff --git a/src/__phutil_library_map__.php b/src/__phutil_library_map__.php
--- a/src/__phutil_library_map__.php
+++ b/src/__phutil_library_map__.php
@@ -1594,6 +1594,7 @@
     'PHUIFeedStoryExample' => 'applications/uiexample/examples/PHUIFeedStoryExample.php',
     'PHUIFeedStoryView' => 'view/phui/PHUIFeedStoryView.php',
     'PHUIFormDividerControl' => 'view/form/control/PHUIFormDividerControl.php',
+    'PHUIFormFileControl' => 'view/form/control/PHUIFormFileControl.php',
     'PHUIFormFreeformDateControl' => 'view/form/control/PHUIFormFreeformDateControl.php',
     'PHUIFormIconSetControl' => 'view/form/control/PHUIFormIconSetControl.php',
     'PHUIFormInsetView' => 'view/form/PHUIFormInsetView.php',
@@ -5996,6 +5997,7 @@
     'PHUIFeedStoryExample' => 'PhabricatorUIExample',
     'PHUIFeedStoryView' => 'AphrontView',
     'PHUIFormDividerControl' => 'AphrontFormControl',
+    'PHUIFormFileControl' => 'AphrontFormControl',
     'PHUIFormFreeformDateControl' => 'AphrontFormControl',
     'PHUIFormIconSetControl' => 'AphrontFormControl',
     'PHUIFormInsetView' => 'AphrontView',
diff --git a/src/applications/files/controller/PhabricatorFileDropUploadController.php b/src/applications/files/controller/PhabricatorFileDropUploadController.php
--- a/src/applications/files/controller/PhabricatorFileDropUploadController.php
+++ b/src/applications/files/controller/PhabricatorFileDropUploadController.php
@@ -56,7 +56,7 @@
       $file_phid = $result['filePHID'];
       if ($file_phid) {
         $file = $this->loadFile($file_phid);
-        $result += $this->getFileDictionary($file);
+        $result += $file->getDragAndDropDictionary();
       }
 
       return id(new AphrontAjaxResponse())->setContent($result);
@@ -84,7 +84,7 @@
       } else {
         $result = array(
           'complete' => true,
-        ) + $this->getFileDictionary($file);
+        ) + $file->getDragAndDropDictionary();
       }
 
       return id(new AphrontAjaxResponse())->setContent($result);
@@ -99,18 +99,10 @@
         'isExplicitUpload' => true,
       ));
 
-    $result = $this->getFileDictionary($file);
+    $result = $file->getDragAndDropDictionary();
     return id(new AphrontAjaxResponse())->setContent($result);
   }
 
-  private function getFileDictionary(PhabricatorFile $file) {
-    return array(
-      'id'   => $file->getID(),
-      'phid' => $file->getPHID(),
-      'uri'  => $file->getBestURI(),
-    );
-  }
-
   private function loadFile($file_phid) {
     $viewer = $this->getViewer();
 
diff --git a/src/applications/files/controller/PhabricatorFileUploadDialogController.php b/src/applications/files/controller/PhabricatorFileUploadDialogController.php
--- a/src/applications/files/controller/PhabricatorFileUploadDialogController.php
+++ b/src/applications/files/controller/PhabricatorFileUploadDialogController.php
@@ -6,12 +6,51 @@
   public function handleRequest(AphrontRequest $request) {
     $viewer = $request->getViewer();
 
-    return $this->newDialog()
-      ->setTitle(pht('Upload File'))
-      ->appendChild(pht(
-        'To add files, drag and drop them into the comment text area.'))
-      ->addCancelButton('/', pht('Close'));
+    $e_file = true;
+    $errors = array();
+    if ($request->isDialogFormPost()) {
+      $file_phids = $request->getStrList('filePHIDs');
+      if ($file_phids) {
+        $files = id(new PhabricatorFileQuery())
+          ->setViewer($viewer)
+          ->withPHIDs($file_phids)
+          ->setRaisePolicyExceptions(true)
+          ->execute();
+      } else {
+        $files = array();
+      }
+
+      if ($files) {
+        $results = array();
+        foreach ($files as $file) {
+          $results[] = $file->getDragAndDropDictionary();
+        }
+
+        $content = array(
+          'files' => $results,
+        );
 
+        return id(new AphrontAjaxResponse())->setContent($content);
+      } else {
+        $e_file = pht('Required');
+        $errors[] = pht('You must choose a file to upload.');
+      }
+    }
+
+    $form = id(new AphrontFormView())
+      ->appendChild(
+        id(new PHUIFormFileControl())
+          ->setName('filePHIDs')
+          ->setLabel(pht('Upload File'))
+          ->setAllowMultiple(true)
+          ->setError($e_file));
+
+    return $this->newDialog()
+      ->setTitle(pht('File'))
+      ->setErrors($errors)
+      ->appendForm($form)
+      ->addSubmitButton(pht('Upload'))
+      ->addCancelButton('/');
   }
 
 }
diff --git a/src/applications/files/storage/PhabricatorFile.php b/src/applications/files/storage/PhabricatorFile.php
--- a/src/applications/files/storage/PhabricatorFile.php
+++ b/src/applications/files/storage/PhabricatorFile.php
@@ -851,6 +851,14 @@
     return $supported;
   }
 
+  public function getDragAndDropDictionary() {
+    return array(
+      'id'   => $this->getID(),
+      'phid' => $this->getPHID(),
+      'uri'  => $this->getBestURI(),
+    );
+  }
+
   public function instantiateStorageEngine() {
     return self::buildEngine($this->getStorageEngine());
   }
diff --git a/src/view/form/control/PHUIFormFileControl.php b/src/view/form/control/PHUIFormFileControl.php
new file mode 100644
--- /dev/null
+++ b/src/view/form/control/PHUIFormFileControl.php
@@ -0,0 +1,44 @@
+<?php
+
+final class PHUIFormFileControl
+  extends AphrontFormControl {
+
+  private $allowMultiple;
+
+  protected function getCustomControlClass() {
+    return 'phui-form-file-upload';
+  }
+
+  public function setAllowMultiple($allow_multiple) {
+    $this->allowMultiple = $allow_multiple;
+    return $this;
+  }
+
+  public function getAllowMultiple() {
+    return $this->allowMultiple;
+  }
+
+  protected function renderInput() {
+    $file_id = $this->getID();
+
+    Javelin::initBehavior(
+      'phui-file-upload',
+      array(
+        'fileInputID' => $file_id,
+        'inputName' => $this->getName(),
+        'uploadURI' => '/file/dropupload/',
+        'chunkThreshold' => PhabricatorFileStorageEngine::getChunkThreshold(),
+      ));
+
+    return phutil_tag(
+      'input',
+      array(
+        'type' => 'file',
+        'multiple' => $this->getAllowMultiple() ? 'multiple' : null,
+        'name' => $this->getName().'.raw',
+        'id' => $file_id,
+        'disabled' => $this->getDisabled() ? 'disabled' : null,
+      ));
+  }
+
+}
diff --git a/webroot/rsrc/externals/javelin/lib/Workflow.js b/webroot/rsrc/externals/javelin/lib/Workflow.js
--- a/webroot/rsrc/externals/javelin/lib/Workflow.js
+++ b/webroot/rsrc/externals/javelin/lib/Workflow.js
@@ -25,7 +25,7 @@
     this.setData(data || {});
   },
 
-  events : ['error', 'finally', 'submit'],
+  events : ['error', 'finally', 'submit', 'start'],
 
   statics : {
     _stack   : [],
@@ -54,6 +54,9 @@
       }
 
       var workflow = new JX.Workflow(form.getAttribute('action'), {});
+
+      workflow._form = form;
+
       workflow.setDataWithListOfPairs(pairs);
       workflow.setMethod(form.getAttribute('method'));
       workflow.listen('finally', function() {
@@ -137,9 +140,14 @@
       data.push([button.name, button.value || true]);
 
       var active = JX.Workflow._getActiveWorkflow();
+
+      active._form = form;
+
       var e = active.invoke('submit', {form: form, data: data});
       if (!e.getStopped()) {
-        active._destroy();
+        // NOTE: Don't remove the current dialog yet because additional
+        // handlers may still want to access the nodes.
+
         active
           .setURI(form.getAttribute('action') || active.getURI())
           .setDataWithListOfPairs(data)
@@ -156,7 +164,41 @@
     _root : null,
     _pushed : false,
     _data : null,
+
+    _form: null,
+    _paused: 0,
+    _nextCallback: null,
+
+    getSourceForm: function() {
+      return this._form;
+    },
+
+    pause: function() {
+      this._paused++;
+      return this;
+    },
+
+    resume: function() {
+      if (!this._paused) {
+        JX.$E('Resuming a workflow which is not paused!');
+      }
+
+      this._paused--;
+
+      if (!this._paused) {
+        var next = this._nextCallback;
+        this._nextCallback = null;
+        if (next) {
+          next();
+        }
+      }
+
+      return this;
+    },
+
     _onload : function(r) {
+      this._destroy();
+
       // It is permissible to send back a falsey redirect to force a page
       // reload, so we need to take this branch if the key is present.
       if (r && (typeof r.redirect != 'undefined')) {
@@ -247,7 +289,19 @@
         this._root = null;
       }
     },
+
     start : function() {
+      var next = JX.bind(this, this._send);
+
+      this.pause();
+      this._nextCallback = next;
+
+      this.invoke('start', this);
+
+      this.resume();
+    },
+
+    _send: function() {
       var uri = this.getURI();
       var method = this.getMethod();
       var r = new JX.Request(uri, JX.bind(this, this._onload));
@@ -291,6 +345,11 @@
       return this;
     },
 
+    addData: function(key, value) {
+      this._data.push([key, value]);
+      return this;
+    },
+
     setDataWithListOfPairs : function(list_of_pairs) {
       this._data = list_of_pairs;
       return this;
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
@@ -155,7 +155,7 @@
 
         var files = e.getRawEvent().dataTransfer.files;
         for (var ii = 0; ii < files.length; ii++) {
-          this._sendRequest(files[ii]);
+          this.sendRequest(files[ii]);
         }
 
         // Force depth to 0.
@@ -216,7 +216,7 @@
               if (!spec.name) {
                 spec.name = 'pasted_file';
               }
-              this._sendRequest(spec);
+              this.sendRequest(spec);
             }
           }));
       }
@@ -224,7 +224,7 @@
       this.setIsEnabled(true);
     },
 
-    _sendRequest : function(spec) {
+    sendRequest : function(spec) {
       var file = new JX.PhabricatorFileUpload()
         .setRawFileObject(spec)
         .setName(spec.name)
diff --git a/webroot/rsrc/js/core/TextAreaUtils.js b/webroot/rsrc/js/core/TextAreaUtils.js
--- a/webroot/rsrc/js/core/TextAreaUtils.js
+++ b/webroot/rsrc/js/core/TextAreaUtils.js
@@ -62,6 +62,26 @@
       JX.TextAreaUtils.setSelectionRange(area, start, end);
     },
 
+
+    /**
+     * Insert a reference to a given uploaded file into a textarea.
+     */
+    insertFileReference: function(area, file) {
+      var ref = '{F' + file.getID() + '}';
+
+      // If we're inserting immediately after a "}" (usually, another file
+      // reference), put some newlines before our token so that multiple file
+      // uploads get laid out more nicely.
+      var range = JX.TextAreaUtils.getSelectionRange(area);
+      var before = area.value.substring(0, range.start);
+      if (before.match(/\}$/)) {
+        ref = '\n\n' + ref;
+      }
+
+      JX.TextAreaUtils.setSelectionText(area, ref, false);
+    },
+
+
     /**
      * Get the document pixel positions of the beginning and end of a character
      * range in a textarea.
diff --git a/webroot/rsrc/js/core/behavior-drag-and-drop-textarea.js b/webroot/rsrc/js/core/behavior-drag-and-drop-textarea.js
--- a/webroot/rsrc/js/core/behavior-drag-and-drop-textarea.js
+++ b/webroot/rsrc/js/core/behavior-drag-and-drop-textarea.js
@@ -10,32 +10,23 @@
 
   var target = JX.$(config.target);
 
-  function onupload(f) {
-    var ref = '{F' + f.getID() + '}';
-
-    // If we're inserting immediately after a "}" (usually, another file
-    // reference), put some newlines before our token so that multiple file
-    // uploads get laid out more nicely.
-    var range = JX.TextAreaUtils.getSelectionRange(target);
-    var before = target.value.substring(0, range.start);
-    if (before.match(/\}$/)) {
-      ref = '\n\n' + ref;
-    }
-
-    JX.TextAreaUtils.setSelectionText(target, ref, false);
-  }
-
   if (JX.PhabricatorDragAndDropFileUpload.isSupported()) {
     var drop = new JX.PhabricatorDragAndDropFileUpload(target)
       .setURI(config.uri)
       .setChunkThreshold(config.chunkThreshold);
+
     drop.listen('didBeginDrag', function() {
       JX.DOM.alterClass(target, config.activatedClass, true);
     });
+
     drop.listen('didEndDrag', function() {
       JX.DOM.alterClass(target, config.activatedClass, false);
     });
-    drop.listen('didUpload', onupload);
+
+    drop.listen('didUpload', function(file) {
+      JX.TextAreaUtils.insertFileReference(target, file);
+    });
+
     drop.start();
   }
 
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
@@ -194,7 +194,21 @@
           .start();
         break;
       case 'fa-cloud-upload':
-        new JX.Workflow('/file/uploaddialog/').start();
+        new JX.Workflow('/file/uploaddialog/')
+          .setHandler(function(response) {
+            var files = response.files;
+            for (var ii = 0; ii < files.length; ii++) {
+              var file = files[ii];
+
+              var upload = new JX.PhabricatorFileUpload()
+                .setID(file.id)
+                .setPHID(file.phid)
+                .setURI(file.uri);
+
+              JX.TextAreaUtils.insertFileReference(area, upload);
+            }
+          })
+          .start();
         break;
       case 'fa-arrows-alt':
         if (edit_mode == 'fa-arrows-alt') {
diff --git a/webroot/rsrc/js/phui/behavior-phui-file-upload.js b/webroot/rsrc/js/phui/behavior-phui-file-upload.js
new file mode 100644
--- /dev/null
+++ b/webroot/rsrc/js/phui/behavior-phui-file-upload.js
@@ -0,0 +1,80 @@
+/**
+ * @provides javelin-behavior-phui-file-upload
+ * @requires javelin-behavior
+ *           javelin-stratcom
+ *           javelin-dom
+ *           phuix-dropdown-menu
+ */
+
+JX.behavior('phui-file-upload', function(config) {
+
+  function startUpload(workflow, input) {
+    var files = input.files;
+
+    if (!files || !files.length) {
+      return;
+    }
+
+    var state = {
+      workflow: workflow,
+      input: input,
+      waiting: 0,
+      phids: []
+    };
+
+    var callback = JX.bind(null, didUpload, state);
+
+    var dummy = input;
+    var uploader = new JX.PhabricatorDragAndDropFileUpload(dummy)
+      .setURI(config.uploadURI)
+      .setChunkThreshold(config.chunkThreshold);
+
+    uploader.listen('didUpload', callback);
+    uploader.start();
+
+    workflow.pause();
+    for (var ii = 0; ii < files.length; ii++) {
+      state.waiting++;
+      uploader.sendRequest(files[ii]);
+    }
+  }
+
+  function didUpload(state, file) {
+    state.phids.push(file.getPHID());
+    state.waiting--;
+
+    if (state.waiting) {
+      return;
+    }
+
+    state.workflow
+      .addData(config.inputName, state.phids.join(', '))
+      .resume();
+  }
+
+  JX.Workflow.listen('start', function(workflow) {
+    var form = workflow.getSourceForm();
+    if (!form) {
+      return;
+    }
+
+    var input;
+    try {
+      input = JX.$(config.fileInputID);
+    } catch (ex) {
+      return;
+    }
+
+    var local_form = JX.DOM.findAbove(input, 'form');
+    if (!local_form) {
+      return;
+    }
+
+    if (local_form !== form) {
+      return;
+    }
+
+    startUpload(workflow, input);
+  });
+
+});