diff --git a/client/constants.js b/client/constants.js
index fa6010aed1..5990b3597a 100644
--- a/client/constants.js
+++ b/client/constants.js
@@ -78,6 +78,7 @@ export const SHOW_FOLDER_CHILDREN = 'SHOW_FOLDER_CHILDREN';
 export const HIDE_FOLDER_CHILDREN = 'HIDE_FOLDER_CHILDREN';
 export const OPEN_UPLOAD_FILE_MODAL = 'OPEN_UPLOAD_FILE_MODAL';
 export const CLOSE_UPLOAD_FILE_MODAL = 'CLOSE_UPLOAD_FILE_MODAL';
+export const INITIALIZE_SIDEBAR_UPLOAD = 'INITIALIZE_SIDEBAR_UPLOAD';
 
 export const SHOW_SHARE_MODAL = 'SHOW_SHARE_MODAL';
 export const CLOSE_SHARE_MODAL = 'CLOSE_SHARE_MODAL';
diff --git a/client/modules/IDE/actions/ide.js b/client/modules/IDE/actions/ide.js
index 80a43443bc..6e4e9d664b 100644
--- a/client/modules/IDE/actions/ide.js
+++ b/client/modules/IDE/actions/ide.js
@@ -91,6 +91,13 @@ export function closeUploadFileModal() {
   };
 }
 
+export function initSidebarUpload(parentId) {
+  return {
+    type: ActionTypes.INITIALIZE_SIDEBAR_UPLOAD,
+    parentId
+  };
+}
+
 export function expandSidebar() {
   return {
     type: ActionTypes.EXPAND_SIDEBAR
diff --git a/client/modules/IDE/actions/uploader.js b/client/modules/IDE/actions/uploader.js
index e2831df75f..54a7886ea9 100644
--- a/client/modules/IDE/actions/uploader.js
+++ b/client/modules/IDE/actions/uploader.js
@@ -22,10 +22,12 @@ export async function dropzoneAcceptCallback(userId, file, done) {
       file.content = await file.text();
       // Make it an error so that it won't be sent to S3, but style as a success.
       done('Uploading plaintext file locally.');
-      file.previewElement.classList.remove('dz-error');
-      file.previewElement.classList.add('dz-success');
-      file.previewElement.classList.add('dz-processing');
-      file.previewElement.querySelector('.dz-upload').style.width = '100%';
+      if (file.previewElement) {
+        file.previewElement.classList.remove('dz-error');
+        file.previewElement.classList.add('dz-success');
+        file.previewElement.classList.add('dz-processing');
+        file.previewElement.querySelector('.dz-upload').style.width = '100%';
+      }
     } catch (error) {
       done(`Failed to download file ${file.name}: ${error}`);
       console.warn(file);
diff --git a/client/modules/IDE/components/Sidebar.jsx b/client/modules/IDE/components/Sidebar.jsx
index 79ffed3b86..23236ddc89 100644
--- a/client/modules/IDE/components/Sidebar.jsx
+++ b/client/modules/IDE/components/Sidebar.jsx
@@ -16,6 +16,7 @@ import { getAuthenticated, selectCanEditSketch } from '../selectors/users';
 import ConnectedFileNode from './FileNode';
 import { PlusIcon } from '../../../common/icons';
 import { FileDrawer } from './Editor/MobileEditor';
+import SidebarFileDragDropUploadWrapper from './SidebarFileDragDropUploadWrapper';
 
 // TODO: use a generic Dropdown UI component
 
@@ -130,7 +131,9 @@ export default function SideBar() {
             </ul>
           </div>
         </header>
-        <ConnectedFileNode id={rootFile.id} canEdit={canEditProject} />
+        <SidebarFileDragDropUploadWrapper>
+          <ConnectedFileNode id={rootFile.id} canEdit={canEditProject} />
+        </SidebarFileDragDropUploadWrapper>
       </section>
     </FileDrawer>
   );
diff --git a/client/modules/IDE/components/SidebarFileDragDropUploadWrapper.jsx b/client/modules/IDE/components/SidebarFileDragDropUploadWrapper.jsx
new file mode 100644
index 0000000000..eaf9067475
--- /dev/null
+++ b/client/modules/IDE/components/SidebarFileDragDropUploadWrapper.jsx
@@ -0,0 +1,128 @@
+import Dropzone from 'dropzone';
+import React, { useEffect } from 'react';
+import PropTypes from 'prop-types';
+import { useDispatch, useSelector } from 'react-redux';
+import { useTranslation } from 'react-i18next';
+import styled from 'styled-components';
+import { fileExtensionsAndMimeTypes } from '../../../../server/utils/fileUtils';
+import {
+  dropzoneAcceptCallback,
+  dropzoneCompleteCallback,
+  dropzoneSendingCallback,
+  s3BucketHttps
+} from '../actions/uploader';
+import { selectActiveFile, selectRootFile } from '../selectors/files';
+import { initSidebarUpload } from '../actions/ide';
+
+Dropzone.autoDiscover = false;
+
+// Styled Components
+const Wrapper = styled.div`
+  height: 100%;
+  display: flex;
+  position: relative;
+`;
+
+const HiddenInputContainer = styled.div``;
+
+const DraggingOverMessage = styled.div`
+  position: absolute;
+  height: 100%;
+  width: 100%;
+  background-color: rgba(0, 0, 0, 0.5);
+  color: rgba(255, 255, 255, 0.85);
+  display: none;
+  justify-content: center;
+  align-items: center;
+  text-align: center;
+  padding: 1rem;
+  font-weight: semibold;
+  transition: background-color 0.3s ease;
+`;
+
+function SidebarFileDragDropUploadWrapper({ children }) {
+  const { t } = useTranslation();
+  const dispatch = useDispatch();
+  const userId = useSelector((state) => state.user.id);
+
+  const rootFile = useSelector(selectRootFile);
+  const activeFile = useSelector(selectActiveFile);
+
+  useEffect(() => {
+    dispatch(
+      initSidebarUpload(
+        activeFile.fileType === 'folder' ? activeFile.id : rootFile.id
+      )
+    );
+
+    let dragCounter = 0;
+
+    const uploader = new Dropzone('div#sidebar-file-drag-drop-upload-wrapper', {
+      url: s3BucketHttps,
+      method: 'post',
+      autoProcessQueue: false,
+      clickable: false,
+      hiddenInputContainer: '#sidebar-hidden-input-container',
+      maxFiles: 6,
+      parallelUploads: 1,
+      maxFilesize: 5, // in MB
+      maxThumbnailFilesize: 8, // in MB
+      thumbnailWidth: 10,
+      previewsContainer: false,
+      thumbnailHeight: 10,
+      acceptedFiles: fileExtensionsAndMimeTypes,
+      dictDefaultMessage: t('FileUploader.DictDefaultMessage'),
+      accept: (file, done) => {
+        dropzoneAcceptCallback(userId, file, done);
+      },
+      sending: dropzoneSendingCallback
+    });
+
+    uploader.on('complete', (file) => {
+      dispatch(dropzoneCompleteCallback(file));
+    });
+
+    uploader.on('dragenter', () => {
+      dragCounter += 1;
+      document.getElementById('dragging-over-message').style.display = 'flex';
+    });
+
+    uploader.on('dragleave', () => {
+      dragCounter -= 1;
+
+      if (dragCounter <= 0) {
+        dragCounter = 0;
+        document.getElementById('dragging-over-message').style.display = 'none';
+      }
+    });
+
+    uploader.on('drop', () => {
+      dragCounter = 0;
+      document.getElementById('dragging-over-message').style.display = 'none';
+    });
+
+    return () => {
+      uploader.off('complete');
+      uploader.off('dragenter');
+      uploader.off('dragleave');
+      uploader.off('drop');
+      uploader.destroy();
+    };
+  }, [userId, dispatch, t, activeFile]);
+
+  return (
+    <Wrapper id="sidebar-file-drag-drop-upload-wrapper">
+      <HiddenInputContainer id="sidebar-hidden-input-container" />
+      {children}
+      <DraggingOverMessage id="dragging-over-message">
+        {t('FileUploader.DictDefaultMessage')}
+      </DraggingOverMessage>
+    </Wrapper>
+  );
+}
+
+SidebarFileDragDropUploadWrapper.propTypes = {
+  children: PropTypes.node.isRequired
+};
+
+export default SidebarFileDragDropUploadWrapper;
diff --git a/client/modules/IDE/reducers/ide.js b/client/modules/IDE/reducers/ide.js
index 8d45b8b50a..09c18faa18 100644
--- a/client/modules/IDE/reducers/ide.js
+++ b/client/modules/IDE/reducers/ide.js
@@ -122,6 +122,8 @@ const ide = (state = initialState, action) => {
       });
     case ActionTypes.CLOSE_UPLOAD_FILE_MODAL:
       return Object.assign({}, state, { uploadFileModalVisible: false });
+    case ActionTypes.INITIALIZE_SIDEBAR_UPLOAD:
+      return Object.assign({}, state, { parentId: action.parentId });
     default:
       return state;
   }