diff --git a/client/modules/IDE/components/Sidebar.jsx b/client/modules/IDE/components/Sidebar.jsx
index 24fd487c9a..a8c15923fd 100644
--- a/client/modules/IDE/components/Sidebar.jsx
+++ b/client/modules/IDE/components/Sidebar.jsx
@@ -124,19 +124,31 @@ export default function SideBar() {
                     {t('Sidebar.AddFile')}
                   </button>
                 </li>
-                {isAuthenticated && (
-                  <li>
-                    <button
-                      aria-label={t('Sidebar.UploadFileARIA')}
-                      onClick={() => {
+                <li>
+                  <button
+                    className={classNames(
+                      !isAuthenticated && 'tooltipped-no-delay',
+                      !isAuthenticated && 'tooltipped',
+                      !isAuthenticated && 'tooltipped-s'
+                    )}
+                    aria-label={
+                      !isAuthenticated
+                        ? t('Sidebar.UploadFileTooltip')
+                        : t('Sidebar.UploadFileARIA')
+                    }
+                    disabled={!isAuthenticated}
+                    onClick={() => {
+                      if (!isAuthenticated) {
+                        window.location.href = '/login';
+                      } else {
                         dispatch(openUploadFileModal(rootFile.id));
                         setTimeout(() => dispatch(closeProjectOptions()), 300);
-                      }}
-                    >
-                      {t('Sidebar.UploadFile')}
-                    </button>
-                  </li>
-                )}
+                      }
+                    }}
+                  >
+                    {t('Sidebar.UploadFile')}
+                  </button>
+                </li>
               </ul>
             )}
           </div>
diff --git a/client/styles/components/_sidebar.scss b/client/styles/components/_sidebar.scss
index 1f1d5972e6..89d051e977 100644
--- a/client/styles/components/_sidebar.scss
+++ b/client/styles/components/_sidebar.scss
@@ -331,4 +331,16 @@
   .sidebar--project-options & {
     display: flex;
   }
+  & button:disabled {
+    @include themify() {
+      opacity: 0.5;
+      cursor: not-allowed;
+    }
+    &:hover {
+      @include themify() {
+        background-color: transparent;
+        color: getThemifyVariable('primary-text-color');
+      }
+    }
+  }
 }
diff --git a/translations/locales/en-US/translations.json b/translations/locales/en-US/translations.json
index 1d254a5afc..e5f7fe3c5a 100644
--- a/translations/locales/en-US/translations.json
+++ b/translations/locales/en-US/translations.json
@@ -275,7 +275,8 @@
     "AddFile": "Create file",
     "AddFileARIA": "add file",
     "UploadFile": "Upload file",
-    "UploadFileARIA": "upload file"
+    "UploadFileARIA": "upload file",
+    "UploadFileTooltip": "Log in to upload file"
   },
   "FileNode": {
     "OpenFolderARIA": "Open folder contents",