diff --git a/web/packages/teleterm/src/ui/TopBar/AdditionalActions.story.tsx b/web/packages/teleterm/src/ui/TopBar/AdditionalActions.story.tsx
new file mode 100644
index 0000000000000..701de28792529
--- /dev/null
+++ b/web/packages/teleterm/src/ui/TopBar/AdditionalActions.story.tsx
@@ -0,0 +1,96 @@
+/**
+ * Copyright 2023 Gravitational, Inc
+ *
+ * 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 * as icons from 'design/Icon';
+
+import { MockAppContextProvider } from 'teleterm/ui/fixtures/MockAppContextProvider';
+
+import { Menu, MenuItem } from './AdditionalActions';
+
+export default {
+  title: 'Teleterm/AdditionalActions',
+};
+
+export const MenuItems = () => {
+  return (
+    <MockAppContextProvider>
+      <Menu
+        css={`
+          max-width: 300px;
+        `}
+      >
+        <MenuItem
+          closeMenu={noop}
+          item={{
+            Icon: icons.Code,
+            isVisible: true,
+            title: 'Regular item',
+            onNavigate: () => {
+              alert('Hello!');
+            },
+          }}
+        />
+        <MenuItem
+          closeMenu={noop}
+          item={{
+            Icon: icons.Moon,
+            isVisible: true,
+            isDisabled: true,
+            title: 'Disabled',
+            disabledText: '…for a reason',
+            onNavigate: noop,
+          }}
+        />
+        <MenuItem
+          closeMenu={noop}
+          item={{
+            Icon: icons.Link,
+            isVisible: true,
+            title: 'With a shortcut',
+            onNavigate: noop,
+            keyboardShortcutAction: 'newTerminalTab',
+          }}
+        />
+        <MenuItem
+          closeMenu={noop}
+          item={{
+            Icon: icons.List,
+            isVisible: true,
+            title: 'With a separator',
+            prependSeparator: true,
+            onNavigate: noop,
+          }}
+        />
+        <MenuItem
+          closeMenu={noop}
+          item={{
+            Icon: icons.Stars,
+            isVisible: true,
+            title: 'With everything',
+            isDisabled: true,
+            disabledText: 'Lorem ipsum dolor sit amet',
+            prependSeparator: true,
+            onNavigate: noop,
+            keyboardShortcutAction: 'previousTab',
+          }}
+        />
+      </Menu>
+    </MockAppContextProvider>
+  );
+};
+
+const noop = () => {};
diff --git a/web/packages/teleterm/src/ui/TopBar/AdditionalActions.tsx b/web/packages/teleterm/src/ui/TopBar/AdditionalActions.tsx
index 793d716d9f078..1d1f2d0b07205 100644
--- a/web/packages/teleterm/src/ui/TopBar/AdditionalActions.tsx
+++ b/web/packages/teleterm/src/ui/TopBar/AdditionalActions.tsx
@@ -32,11 +32,14 @@ import { useNewTabOpener } from 'teleterm/ui/TabHost';
 type MenuItem = {
   title: string;
   isVisible: boolean;
-  Icon: React.ComponentType<{ fontSize: number }>;
+  Icon: React.ElementType;
   onNavigate: () => void;
   prependSeparator?: boolean;
   keyboardShortcutAction?: KeyboardShortcutAction;
-};
+} & (MenuItemAlwaysEnabled | MenuItemConditionallyDisabled);
+
+type MenuItemAlwaysEnabled = { isDisabled?: false };
+type MenuItemConditionallyDisabled = { isDisabled: true; disabledText: string };
 
 function useMenuItems(): MenuItem[] {
   const ctx = useAppContext();
@@ -51,6 +54,7 @@ function useMenuItems(): MenuItem[] {
     localClusterUri: workspacesService.getActiveWorkspace()?.localClusterUri,
   });
 
+  const hasNoActiveWorkspace = !documentsService;
   const areAccessRequestsSupported =
     !!activeRootCluster?.features?.advancedAccessWorkflows;
 
@@ -61,6 +65,9 @@ function useMenuItems(): MenuItem[] {
     {
       title: 'Open new terminal',
       isVisible: true,
+      isDisabled: hasNoActiveWorkspace,
+      disabledText:
+        'You need to be logged in to a cluster to open new terminals.',
       Icon: icons.Terminal,
       keyboardShortcutAction: 'newTerminalTab',
       onNavigate: openTerminalTab,
@@ -137,10 +144,11 @@ export function AdditionalActions() {
 
   const items = useMenuItems().map(item => {
     return (
-      <React.Fragment key={item.title}>
-        {item.prependSeparator && <Separator />}
-        <MenuItem item={item} closeMenu={() => setIsPopoverOpened(false)} />
-      </React.Fragment>
+      <MenuItem
+        key={item.title}
+        item={item}
+        closeMenu={() => setIsPopoverOpened(false)}
+      />
     );
   });
 
@@ -168,7 +176,7 @@ export function AdditionalActions() {
   );
 }
 
-const Menu = styled.menu`
+export const Menu = styled.menu`
   list-style: none;
   padding: 0;
   margin: 0;
@@ -183,7 +191,7 @@ const Separator = styled.div`
   height: 1px;
 `;
 
-function MenuItem({
+export function MenuItem({
   item,
   closeMenu,
 }: {
@@ -197,32 +205,44 @@ function MenuItem({
   };
 
   return (
-    <StyledListItem as="button" type="button" onClick={handleClick}>
-      <item.Icon fontSize={2} />
-      <Flex
-        gap={2}
-        flex="1"
-        alignItems="baseline"
-        justifyContent="space-between"
+    <>
+      {item.prependSeparator && <Separator />}
+      <StyledListItem
+        as="button"
+        type="button"
+        disabled={item.isDisabled}
+        title={item.isDisabled && item.disabledText}
+        onClick={handleClick}
       >
-        <Text>{item.title}</Text>
-
-        {item.keyboardShortcutAction && (
-          <Text
-            fontSize={1}
-            css={`
-              border-radius: 4px;
-              width: fit-content;
-              padding: ${props => props.theme.space[1]}px
-                ${props => props.theme.space[1]}px;
-            `}
-            bg="levels.surface"
-          >
-            {getAccelerator(item.keyboardShortcutAction)}
-          </Text>
-        )}
-      </Flex>
-    </StyledListItem>
+        <item.Icon color={item.isDisabled && 'text.disabled'} fontSize={2} />
+        <Flex
+          gap={2}
+          flex="1"
+          alignItems="baseline"
+          justifyContent="space-between"
+        >
+          <Text>{item.title}</Text>
+
+          {item.keyboardShortcutAction && (
+            <Text
+              fontSize={1}
+              css={`
+                border-radius: 4px;
+                width: fit-content;
+                // Using a background with an alpha color to make this interact better with the
+                // disabled state.
+                background-color: ${props =>
+                  props.theme.colors.spotBackground[0]};
+                padding: ${props => props.theme.space[1]}px
+                  ${props => props.theme.space[1]}px;
+              `}
+            >
+              {getAccelerator(item.keyboardShortcutAction)}
+            </Text>
+          )}
+        </Flex>
+      </StyledListItem>
+    </>
   );
 }
 
@@ -231,4 +251,13 @@ const StyledListItem = styled(ListItem)`
   gap: ${props => props.theme.space[3]}px;
   padding: 0 ${props => props.theme.space[3]}px;
   border-radius: 0;
+
+  &:disabled {
+    cursor: default;
+    color: ${props => props.theme.colors.text.disabled};
+
+    &:hover {
+      background-color: inherit;
+    }
+  }
 `;