diff --git a/app/javascript/flavours/glitch/actions/alerts.js b/app/javascript/flavours/glitch/actions/alerts.js
index 3f5d7ef46..50cd48a9e 100644
--- a/app/javascript/flavours/glitch/actions/alerts.js
+++ b/app/javascript/flavours/glitch/actions/alerts.js
@@ -22,7 +22,7 @@ export function clearAlert() {
   };
 };
 
-export function showAlert(title, message) {
+export function showAlert(title = messages.unexpectedTitle, message = messages.unexpectedMessage) {
   return {
     type: ALERT_SHOW,
     title,
@@ -44,6 +44,6 @@ export function showAlertForError(error) {
     return showAlert(title, message);
   } else {
     console.error(error);
-    return showAlert(messages.unexpectedTitle, messages.unexpectedMessage);
+    return showAlert();
   }
 }
diff --git a/app/javascript/flavours/glitch/actions/compose.js b/app/javascript/flavours/glitch/actions/compose.js
index 204d609b0..0dd1766bc 100644
--- a/app/javascript/flavours/glitch/actions/compose.js
+++ b/app/javascript/flavours/glitch/actions/compose.js
@@ -9,6 +9,8 @@ import resizeImage from 'flavours/glitch/util/resize_image';
 
 import { updateTimeline } from './timelines';
 import { showAlertForError } from './alerts';
+import { showAlert } from './alerts';
+import { defineMessages } from 'react-intl';
 
 let cancelFetchComposeSuggestionsAccounts;
 
@@ -53,6 +55,10 @@ export const COMPOSE_UPLOAD_CHANGE_FAIL        = 'COMPOSE_UPLOAD_UPDATE_FAIL';
 
 export const COMPOSE_DOODLE_SET        = 'COMPOSE_DOODLE_SET';
 
+const messages = defineMessages({
+  uploadErrorLimit: { id: 'upload_error.limit', defaultMessage: 'File upload limit exceeded.' },
+});
+
 export function changeCompose(text) {
   return {
     type: COMPOSE_CHANGE,
@@ -208,20 +214,32 @@ export function doodleSet(options) {
 
 export function uploadCompose(files) {
   return function (dispatch, getState) {
-    if (getState().getIn(['compose', 'media_attachments']).size > 3) {
+    const uploadLimit = 4;
+    const media  = getState().getIn(['compose', 'media_attachments']);
+    const total = Array.from(files).reduce((a, v) => a + v.size, 0);
+    const progress = new Array(files.length).fill(0);
+
+    if (files.length + media.size > uploadLimit) {
+      dispatch(showAlert(undefined, messages.uploadErrorLimit));
       return;
     }
-
     dispatch(uploadComposeRequest());
 
-    resizeImage(files[0]).then(file => {
-      const data = new FormData();
-      data.append('file', file);
-
-      return api(getState).post('/api/v1/media', data, {
-        onUploadProgress: ({ loaded, total }) => dispatch(uploadComposeProgress(loaded, total)),
-      }).then(({ data }) => dispatch(uploadComposeSuccess(data)));
-    }).catch(error => dispatch(uploadComposeFail(error)));
+    for (const [i, f] of Array.from(files).entries()) {
+      if (media.size + i > 3) break;
+
+      resizeImage(f).then(file => {
+        const data = new FormData();
+        data.append('file', file);
+
+        return api(getState).post('/api/v1/media', data, {
+          onUploadProgress: function({ loaded }){
+            progress[i] = loaded;
+            dispatch(uploadComposeProgress(progress.reduce((a, v) => a + v, 0), total));
+          },
+        }).then(({ data }) => dispatch(uploadComposeSuccess(data)));
+      }).catch(error => dispatch(uploadComposeFail(error)));
+    };
   };
 };
 
diff --git a/app/javascript/flavours/glitch/features/composer/options/index.js b/app/javascript/flavours/glitch/features/composer/options/index.js
index 9fe3abc03..5b4a7444c 100644
--- a/app/javascript/flavours/glitch/features/composer/options/index.js
+++ b/app/javascript/flavours/glitch/features/composer/options/index.js
@@ -214,6 +214,7 @@ export default class ComposerOptions extends React.PureComponent {
           onChange={handleChangeFiles}
           ref={handleRefFileElement}
           type='file'
+          multiple
           {...hiddenComponent}
         />
         <Dropdown
diff --git a/app/javascript/flavours/glitch/features/ui/index.js b/app/javascript/flavours/glitch/features/ui/index.js
index 602d93832..a19b3abf1 100644
--- a/app/javascript/flavours/glitch/features/ui/index.js
+++ b/app/javascript/flavours/glitch/features/ui/index.js
@@ -186,7 +186,7 @@ export default class UI extends React.Component {
     this.setState({ draggingOver: false });
     this.dragTargets = [];
 
-    if (e.dataTransfer && e.dataTransfer.files.length === 1) {
+    if (e.dataTransfer && e.dataTransfer.files.length >= 1) {
       this.props.dispatch(uploadCompose(e.dataTransfer.files));
     }
   }