diff --git a/packages/core-components/src/layout/Sidebar/Bar.test.tsx b/packages/core-components/src/layout/Sidebar/Bar.test.tsx
new file mode 100644
index 0000000000..8a28d69e27
--- /dev/null
+++ b/packages/core-components/src/layout/Sidebar/Bar.test.tsx
@@ -0,0 +1,104 @@
+/*
+ * Copyright 2020 The Backstage Authors
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+import React from 'react';
+import { renderInTestApp } from '@backstage/test-utils';
+import { createEvent, fireEvent, screen, within } from '@testing-library/react';
+import userEvent from '@testing-library/user-event';
+import BuildRoundedIcon from '@material-ui/icons/BuildRounded';
+import CreateComponentIcon from '@material-ui/icons/AddCircleOutline';
+import { CatalogSidebarLogo } from './icons/CatalogSidebarLogo';
+import { MiscIcon } from './icons/MiscIcon';
+import { Sidebar, SidebarExpandButton } from './Bar';
+import { SidebarItem, SidebarSearchField } from './Items';
+import { hexToRgb } from '@material-ui/core/styles';
+import { SubmenuItem } from './SubmenuItem';
+
+async function renderScalableSidebar() {
+  await renderInTestApp(
+    <Sidebar>
+      <SidebarSearchField onSearch={() => {}} to="/search" />
+      <SidebarItem
+        icon={CatalogSidebarLogo}
+        onClick={() => {}}
+        text="Catalog"
+        hasSubMenu
+        submenuTitle="Catalog"
+      >
+        <SubmenuItem title="Tools" to="/1" icon={BuildRoundedIcon} />
+        <SubmenuItem
+          title="Misc"
+          to="/6"
+          icon={MiscIcon}
+          hasDropDown
+          dropdownItems={[
+            {
+              title: 'dropdown item 1',
+              to: '/dropdownitemlink',
+            },
+            {
+              title: 'dropdown item 2',
+              to: '/dropdownitemlink2',
+            },
+          ]}
+        />
+      </SidebarItem>
+      <SidebarItem icon={CreateComponentIcon} to="create" text="Create..." />
+      <SidebarExpandButton />
+    </Sidebar>,
+  );
+}
+
+describe('Sidebar', () => {
+  beforeEach(async () => {
+    await renderScalableSidebar();
+  });
+
+  describe('Click to Expand', () => {
+    it('Sidebar should show expanded items when expand button is clicked', async () => {
+      userEvent.click(screen.getByTestId('sidebar-expand-button'));
+      expect(await screen.findByText('Create...')).toBeInTheDocument();
+    });
+  });
+  describe('Submenu Items', () => {
+    it('Extended sidebar with submenu content hidden by default', async () => {
+      expect(await screen.queryByText('Tools')).not.toBeInTheDocument();
+      expect(await screen.queryByText('Misc')).not.toBeInTheDocument();
+    });
+
+    it('Extended sidebar with submenu content visible when hover over submenu items', async () => {
+      userEvent.hover(screen.getByTestId('item-with-submenu'));
+      expect(await screen.findByText('Tools')).toBeInTheDocument();
+      expect(await screen.findByText('Misc')).toBeInTheDocument();
+    });
+
+    it('Multicategory item in submenu shows drop down on click', async () => {
+      userEvent.hover(screen.getByTestId('item-with-submenu'));
+      userEvent.click(screen.getByText('Misc'));
+      expect(await screen.getByText('dropdown item 1')).toBeInTheDocument();
+      expect(await screen.getByText('dropdown item 2')).toBeInTheDocument();
+    });
+
+    it('Dropdown item in submenu renders a link when `to` value is provided', async () => {
+      userEvent.hover(screen.getByTestId('item-with-submenu'));
+      userEvent.click(screen.getByText('Misc'));
+      expect(screen.getByText('dropdown item 1').closest('a')).toHaveAttribute(
+        'href',
+        '/dropdownitemlink',
+      );
+    });
+  });
+});
diff --git a/packages/core-components/src/layout/Sidebar/Bar.tsx b/packages/core-components/src/layout/Sidebar/Bar.tsx
index 6fc2ac1cdb..23a4ae1286 100644
--- a/packages/core-components/src/layout/Sidebar/Bar.tsx
+++ b/packages/core-components/src/layout/Sidebar/Bar.tsx
@@ -146,7 +146,12 @@ export const SidebarExpandButton = () => {
   }
 
   return (
-    <button onClick={handleClick} className={classes.expandButton}>
+    <button
+      onClick={handleClick}
+      className={classes.expandButton}
+      aria-label="Expand Sidebar"
+      data-testid="sidebar-expand-button"
+    >
       <div className={classes.arrows}>
         {isOpen ? <DoubleArrowLeft /> : <DoubleArrowRight />}
       </div>
diff --git a/packages/core-components/src/layout/Sidebar/Items.tsx b/packages/core-components/src/layout/Sidebar/Items.tsx
index 1c15367ced..9c368cd73d 100644
--- a/packages/core-components/src/layout/Sidebar/Items.tsx
+++ b/packages/core-components/src/layout/Sidebar/Items.tsx
@@ -253,6 +253,7 @@ const ItemWithSubmenu = ({
       >
         <div
           onMouseEnter={handleMouseEnter}
+          data-testid="item-with-submenu"
           className={clsx(
             classes.root,
             isOpen ? classes.open : classes.closed,
diff --git a/packages/core-components/src/layout/Sidebar/Submenu.tsx b/packages/core-components/src/layout/Sidebar/Submenu.tsx
index 0f6ce80520..73033164b4 100644
--- a/packages/core-components/src/layout/Sidebar/Submenu.tsx
+++ b/packages/core-components/src/layout/Sidebar/Submenu.tsx
@@ -13,7 +13,8 @@
  * See the License for the specific language governing permissions and
  * limitations under the License.
  */
-import { makeStyles, Typography } from '@material-ui/core';
+import { makeStyles } from '@material-ui/core/styles';
+import Typography from '@material-ui/core/Typography';
 import clsx from 'clsx';
 import React, { PropsWithChildren, ReactNode, useContext } from 'react';
 import {
diff --git a/packages/core-components/src/layout/Sidebar/SubmenuItem.tsx b/packages/core-components/src/layout/Sidebar/SubmenuItem.tsx
index b34a9aa269..e5c49c3b07 100644
--- a/packages/core-components/src/layout/Sidebar/SubmenuItem.tsx
+++ b/packages/core-components/src/layout/Sidebar/SubmenuItem.tsx
@@ -20,7 +20,9 @@ import {
   useLocation,
   useResolvedPath,
 } from 'react-router-dom';
-import { Link, makeStyles, Typography } from '@material-ui/core';
+import { makeStyles } from '@material-ui/core/styles';
+import Typography from '@material-ui/core/Typography';
+import Link from '@material-ui/core/Link';
 import { IconComponent } from '@backstage/core-plugin-api';
 import clsx from 'clsx';
 import { BackstageTheme } from '@backstage/theme';