diff --git a/shell/browser/native_window_mac.mm b/shell/browser/native_window_mac.mm
index e56fad7eacd22..1438806d3e5a6 100644
--- a/shell/browser/native_window_mac.mm
+++ b/shell/browser/native_window_mac.mm
@@ -1140,6 +1140,8 @@ void ViewDidMoveToSuperview(NSView* self, SEL _cmd) {
 
 void NativeWindowMac::SetDocumentEdited(bool edited) {
   [window_ setDocumentEdited:edited];
+  if (buttons_proxy_)
+    [buttons_proxy_ redraw];
 }
 
 bool NativeWindowMac::IsDocumentEdited() {