diff --git a/static/app/views/explore/toolbar/index.spec.tsx b/static/app/views/explore/toolbar/index.spec.tsx
index c9412146b499ec..ef7132929343b9 100644
--- a/static/app/views/explore/toolbar/index.spec.tsx
+++ b/static/app/views/explore/toolbar/index.spec.tsx
@@ -265,7 +265,13 @@ describe('ExploreToolbar', function () {
     await userEvent.click(within(section).getAllByLabelText('Remove')[0]);
     expect(groupBys).toEqual(['span.description']);
 
-    // only one left so cant be deleted
+    // only 1 left but it's not empty
+    expect(within(section).getByLabelText('Remove')).toBeEnabled();
+
+    await userEvent.click(within(section).getByLabelText('Remove'));
+    expect(groupBys).toEqual(['']);
+
+    // last one and it's empty
     expect(within(section).getByLabelText('Remove')).toBeDisabled();
   });
 });
diff --git a/static/app/views/explore/toolbar/toolbarGroupBy.tsx b/static/app/views/explore/toolbar/toolbarGroupBy.tsx
index cee5ed73105c3e..f466615f71e194 100644
--- a/static/app/views/explore/toolbar/toolbarGroupBy.tsx
+++ b/static/app/views/explore/toolbar/toolbarGroupBy.tsx
@@ -89,7 +89,7 @@ export function ToolbarGroupBy({disabled}: ToolbarGroupByProps) {
               borderless
               icon={<IconDelete />}
               size="zero"
-              disabled={disabled || groupBys.length <= 1}
+              disabled={disabled || (groupBys.length <= 1 && groupBy === '')}
               onClick={() => deleteGroupBy(index)}
               aria-label={t('Remove')}
             />