diff --git a/shell/browser/native_window_mac.mm b/shell/browser/native_window_mac.mm
index ac68f39a8e4a5..ec21ba682e719 100644
--- a/shell/browser/native_window_mac.mm
+++ b/shell/browser/native_window_mac.mm
@@ -1136,6 +1136,8 @@ void ViewDidMoveToSuperview(NSView* self, SEL _cmd) {
 
 void NativeWindowMac::SetDocumentEdited(bool edited) {
   [window_ setDocumentEdited:edited];
+  if (buttons_proxy_)
+    [buttons_proxy_ redraw];
 }
 
 bool NativeWindowMac::IsDocumentEdited() {