diff --git a/shell/browser/native_window_mac.mm b/shell/browser/native_window_mac.mm
index 2c0a3b3f8c5e..45eef7e744f8 100644
--- a/shell/browser/native_window_mac.mm
+++ b/shell/browser/native_window_mac.mm
@@ -352,8 +352,11 @@ void NativeWindowMac::Close() {
   // [window_ performClose:nil], the window won't close properly
   // even after the user has ended the sheet.
   // Ensure it's closed before calling [window_ performClose:nil].
-  if ([window_ attachedSheet])
+  // If multiple sheets are open, they must all be closed.
+  while ([window_ attachedSheet]) {
     [window_ endSheet:[window_ attachedSheet]];
+  }
+  DCHECK_EQ([[window_ sheets] count], 0UL);
 
   // window_ could be nil after performClose.
   bool should_notify = is_modal() && parent() && IsVisible();
diff --git a/spec/api-browser-window-spec.ts b/spec/api-browser-window-spec.ts
index debae0bf4be8..6d3ba73d8fa4 100644
--- a/spec/api-browser-window-spec.ts
+++ b/spec/api-browser-window-spec.ts
@@ -117,6 +117,14 @@ describe('BrowserWindow module', () => {
       await closed;
     });
 
+    it('should work if called when multiple messageBoxes are showing', async () => {
+      const closed = once(w, 'closed');
+      dialog.showMessageBox(w, { message: 'Hello Error' });
+      dialog.showMessageBox(w, { message: 'Hello Error' });
+      w.close();
+      await closed;
+    });
+
     it('closes window without rounded corners', async () => {
       await closeWindow(w);
       w = new BrowserWindow({ show: false, frame: false, roundedCorners: false });