diff --git a/frontend/components/Editor/components/Image.js b/frontend/components/Editor/components/Image.js
index d7841f37c..aacbf36b2 100644
--- a/frontend/components/Editor/components/Image.js
+++ b/frontend/components/Editor/components/Image.js
@@ -1,13 +1,16 @@
 // @flow
 import React from 'react';
 import type { Props } from '../types';
+import styled from 'styled-components';
+
+const LoadingImage = styled.img`
+  opacity: .5;
+`;
 
 export default function Image({ attributes, node }: Props) {
-  return (
-    <img
-      {...attributes}
-      src={node.data.get('src')}
-      alt={node.data.get('alt')}
-    />
-  );
+  const loading = node.data.get('loading');
+  const Component = loading ? LoadingImage : 'img';
+  const src = node.data.get('inlineSrc') || node.data.get('src');
+
+  return <Component {...attributes} src={src} alt={node.data.get('alt')} />;
 }
diff --git a/frontend/components/Editor/plugins.js b/frontend/components/Editor/plugins.js
index af9fd158b..dfd0d1559 100644
--- a/frontend/components/Editor/plugins.js
+++ b/frontend/components/Editor/plugins.js
@@ -1,14 +1,13 @@
 // @flow
-import DropOrPasteImages from 'slate-drop-or-paste-images';
 import PasteLinkify from 'slate-paste-linkify';
 import EditList from 'slate-edit-list';
 import CollapseOnEscape from 'slate-collapse-on-escape';
 import TrailingBlock from 'slate-trailing-block';
 import EditCode from 'slate-edit-code';
 import Prism from 'slate-prism';
-import uploadFile from 'utils/uploadFile';
 import KeyboardShortcuts from './plugins/KeyboardShortcuts';
 import MarkdownShortcuts from './plugins/MarkdownShortcuts';
+import ImageUploads from './plugins/ImageUploads';
 
 const onlyInCode = node => node.type === 'code';
 
@@ -17,34 +16,13 @@ type Options = {
   onImageUploadStop: Function,
 };
 
-const createPlugins = ({ onImageUploadStart, onImageUploadStop }: Options) => {
+const createPlugins = (options: Options) => {
   return [
     PasteLinkify({
       type: 'link',
       collapseTo: 'end',
     }),
-    DropOrPasteImages({
-      extensions: ['png', 'jpg', 'gif'],
-      applyTransform: async (transform, file) => {
-        onImageUploadStart();
-        try {
-          const asset = await uploadFile(file);
-          const alt = file.name;
-          const src = asset.url;
-
-          return transform.insertBlock({
-            type: 'image',
-            isVoid: true,
-            data: { src, alt },
-          });
-        } catch (err) {
-          // TODO: Show a failure alert
-          console.error(err);
-        } finally {
-          onImageUploadStop();
-        }
-      },
-    }),
+    ImageUploads(options),
     EditList({
       types: ['ordered-list', 'bulleted-list', 'todo-list'],
       typeItem: 'list-item',
diff --git a/frontend/components/Editor/plugins/ImageUploads.js b/frontend/components/Editor/plugins/ImageUploads.js
new file mode 100644
index 000000000..e7967f616
--- /dev/null
+++ b/frontend/components/Editor/plugins/ImageUploads.js
@@ -0,0 +1,63 @@
+// @flow
+import uuid from 'uuid';
+import DropOrPasteImages from 'slate-drop-or-paste-images';
+import uploadFile from 'utils/uploadFile';
+
+type Options = {
+  onImageUploadStart: Function,
+  onImageUploadStop: Function,
+};
+
+export default function ImageUploads({
+  onImageUploadStart,
+  onImageUploadStop,
+}: Options) {
+  return DropOrPasteImages({
+    extensions: ['png', 'jpg', 'gif'],
+    applyTransform: async (transform, editor, file) => {
+      onImageUploadStart();
+
+      // load the file as a data URL
+      const id = uuid.v4();
+      const alt = file.name;
+      const reader = new FileReader();
+      reader.addEventListener('load', () => {
+        const src = reader.result;
+
+        // insert into document as uploading placeholder
+        const state = transform
+          .insertBlock({
+            type: 'image',
+            isVoid: true,
+            data: { src, alt, id, loading: true },
+          })
+          .apply();
+        editor.onChange(state);
+      });
+      reader.readAsDataURL(file);
+
+      // now we have a placeholder, start the upload
+      try {
+        const asset = await uploadFile(file);
+        const src = asset.url;
+
+        // we dont use the original transform provided to the callback here
+        // as the state may have changed significantly in the time it took to
+        // upload the file.
+        const state = editor.getState();
+        const transform = state.transform();
+        const placeholder = state.document.findDescendant(
+          node => node.data && node.data.get('id') === id
+        );
+        return transform.setNodeByKey(placeholder.key, {
+          data: { src, alt, loading: false },
+        });
+      } catch (err) {
+        // TODO: Show a failure alert
+        console.error(err);
+      } finally {
+        onImageUploadStop();
+      }
+    },
+  });
+}
diff --git a/package.json b/package.json
index dfa1cd5f4..8ddc39b45 100644
--- a/package.json
+++ b/package.json
@@ -158,7 +158,7 @@
     "sequelize-encrypted": "0.1.0",
     "slate": "^0.19.30",
     "slate-collapse-on-escape": "^0.2.1",
-    "slate-drop-or-paste-images": "^0.5.0",
+    "slate-drop-or-paste-images": "tommoor/slate-drop-or-paste-images",
     "slate-edit-code": "^0.10.2",
     "slate-edit-list": "^0.7.0",
     "slate-markdown-serializer": "tommoor/slate-markdown-serializer",
diff --git a/yarn.lock b/yarn.lock
index 810762be4..1f8073b6c 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -2501,11 +2501,7 @@ emoji-name-map@1.1.2:
     iterate-object "^1.3.1"
     map-o "^2.0.1"
 
-emoji-regex@^6.1.0:
-  version "6.4.2"
-  resolved "https://registry.yarnpkg.com/emoji-regex/-/emoji-regex-6.4.2.tgz#a30b6fee353d406d96cfb9fa765bdc82897eff6e"
-
-emoji-regex@^6.5.1:
+emoji-regex@^6.1.0, emoji-regex@^6.5.1:
   version "6.5.1"
   resolved "https://registry.yarnpkg.com/emoji-regex/-/emoji-regex-6.5.1.tgz#9baea929b155565c11ea41c6626eaa65cef992c2"
 
@@ -8013,9 +8009,9 @@ slate-collapse-on-escape@^0.2.1:
   dependencies:
     to-pascal-case "^1.0.0"
 
-slate-drop-or-paste-images@^0.5.0:
+slate-drop-or-paste-images@tommoor/slate-drop-or-paste-images:
   version "0.5.0"
-  resolved "https://registry.yarnpkg.com/slate-drop-or-paste-images/-/slate-drop-or-paste-images-0.5.0.tgz#c90367f9612f75abae0d1d6b8b2008108da02598"
+  resolved "https://codeload.github.com/tommoor/slate-drop-or-paste-images/tar.gz/a3ebc74658941ec2c56d4b90493b8718b8a9fd4f"
   dependencies:
     data-uri-to-blob "0.0.4"
     es6-promise "^4.0.5"