diff --git a/src/__phutil_library_map__.php b/src/__phutil_library_map__.php
index 918a1f4105..f482fe3c26 100644
--- a/src/__phutil_library_map__.php
+++ b/src/__phutil_library_map__.php
@@ -1009,6 +1009,7 @@ phutil_register_library_map(array(
     'PhabricatorFileTestDataGenerator' => 'applications/files/lipsum/PhabricatorFileTestDataGenerator.php',
     'PhabricatorFileTransformController' => 'applications/files/controller/PhabricatorFileTransformController.php',
     'PhabricatorFileUploadController' => 'applications/files/controller/PhabricatorFileUploadController.php',
+    'PhabricatorFileUploadDialogController' => 'applications/files/controller/PhabricatorFileUploadDialogController.php',
     'PhabricatorFileUploadException' => 'applications/files/exception/PhabricatorFileUploadException.php',
     'PhabricatorFilesConfigOptions' => 'applications/files/config/PhabricatorFilesConfigOptions.php',
     'PhabricatorFilesManagementEnginesWorkflow' => 'applications/files/management/PhabricatorFilesManagementEnginesWorkflow.php',
@@ -2805,6 +2806,7 @@ phutil_register_library_map(array(
     'PhabricatorFileTestDataGenerator' => 'PhabricatorTestDataGenerator',
     'PhabricatorFileTransformController' => 'PhabricatorFileController',
     'PhabricatorFileUploadController' => 'PhabricatorFileController',
+    'PhabricatorFileUploadDialogController' => 'PhabricatorFileController',
     'PhabricatorFileUploadException' => 'Exception',
     'PhabricatorFilesConfigOptions' => 'PhabricatorApplicationConfigOptions',
     'PhabricatorFilesManagementEnginesWorkflow' => 'PhabricatorFilesManagementWorkflow',
diff --git a/src/applications/files/application/PhabricatorApplicationFiles.php b/src/applications/files/application/PhabricatorApplicationFiles.php
index 2d79ac1003..5d7d45258b 100644
--- a/src/applications/files/application/PhabricatorApplicationFiles.php
+++ b/src/applications/files/application/PhabricatorApplicationFiles.php
@@ -49,6 +49,7 @@ final class PhabricatorApplicationFiles extends PhabricatorApplication {
         'proxy/' => 'PhabricatorFileProxyController',
         'xform/(?P<transform>[^/]+)/(?P<phid>[^/]+)/(?P<key>[^/]+)/'
           => 'PhabricatorFileTransformController',
+        'uploaddialog/' => 'PhabricatorFileUploadDialogController',
       ),
     );
   }
diff --git a/src/applications/files/controller/PhabricatorFileUploadDialogController.php b/src/applications/files/controller/PhabricatorFileUploadDialogController.php
new file mode 100644
index 0000000000..3928a3b14b
--- /dev/null
+++ b/src/applications/files/controller/PhabricatorFileUploadDialogController.php
@@ -0,0 +1,20 @@
+<?php
+
+final class PhabricatorFileUploadDialogController
+  extends PhabricatorFileController {
+
+  public function processRequest() {
+    $request = $this->getRequest();
+    $user = $request->getUser();
+
+    $dialog = id(new AphrontDialogView())
+      ->setUser($user)
+      ->setTitle(pht('Upload Image'))
+      ->appendChild(pht(
+        'To add files, drag and drop them into the comment text area.'))
+      ->addCancelButton('/', pht('Close'));
+
+    return id(new AphrontDialogResponse())->setDialog($dialog);
+  }
+
+}
diff --git a/src/applications/maniphest/controller/ManiphestTaskDetailController.php b/src/applications/maniphest/controller/ManiphestTaskDetailController.php
index 1292a90f76..3992d4c783 100644
--- a/src/applications/maniphest/controller/ManiphestTaskDetailController.php
+++ b/src/applications/maniphest/controller/ManiphestTaskDetailController.php
@@ -257,11 +257,6 @@ final class ManiphestTaskDetailController extends ManiphestController {
           ->setValue($draft_text)
           ->setID('transaction-comments')
           ->setUser($user))
-      ->appendChild(
-        id(new AphrontFormDragAndDropUploadControl())
-          ->setLabel(pht('Attached Files'))
-          ->setName('files')
-          ->setActivatedClass('aphront-panel-view-drag-and-drop'))
       ->appendChild(
         id(new AphrontFormSubmitControl())
           ->setValue($is_serious ? pht('Submit') : pht('Avast!')));
diff --git a/src/applications/maniphest/controller/ManiphestTaskEditController.php b/src/applications/maniphest/controller/ManiphestTaskEditController.php
index afde05d34a..4290abdb1a 100644
--- a/src/applications/maniphest/controller/ManiphestTaskEditController.php
+++ b/src/applications/maniphest/controller/ManiphestTaskEditController.php
@@ -485,15 +485,6 @@ final class ManiphestTaskEditController extends ManiphestController {
     $form
       ->appendChild($description_control);
 
-    if (!$task->getID()) {
-      $form
-        ->appendChild(
-          id(new AphrontFormDragAndDropUploadControl())
-            ->setLabel(pht('Attached Files'))
-            ->setName('files')
-            ->setActivatedClass('aphront-panel-view-drag-and-drop'));
-    }
-
     $form
       ->appendChild(
         id(new AphrontFormSubmitControl())
diff --git a/src/view/form/control/PhabricatorRemarkupControl.php b/src/view/form/control/PhabricatorRemarkupControl.php
index c71c0d162e..728f68c748 100644
--- a/src/view/form/control/PhabricatorRemarkupControl.php
+++ b/src/view/form/control/PhabricatorRemarkupControl.php
@@ -54,8 +54,12 @@ final class PhabricatorRemarkupControl extends AphrontFormTextAreaControl {
       ),
       'table' => array(
         'tip' => pht('Table'),
-      )
+      ),
+      'image' => array(
+        'tip' => pht('Upload File'),
+      ),
     );
+
     if (!$this->disableMacro and function_exists('imagettftext')) {
       $actions[] = array(
         'spacer' => true,
diff --git a/webroot/rsrc/js/core/behavior-phabricator-remarkup-assist.js b/webroot/rsrc/js/core/behavior-phabricator-remarkup-assist.js
index 1152bedd6a..ef01e1d908 100644
--- a/webroot/rsrc/js/core/behavior-phabricator-remarkup-assist.js
+++ b/webroot/rsrc/js/core/behavior-phabricator-remarkup-assist.js
@@ -174,6 +174,9 @@ JX.behavior('phabricator-remarkup-assist', function(config) {
           })
           .start();
         break;
+      case 'image':
+        new JX.Workflow('/file/uploaddialog/').start();
+        break;
       case 'chaos':
         if (edit_mode == 'chaos') {
           set_edit_mode(root, 'normal');