diff --git a/shell/browser/native_window_mac.mm b/shell/browser/native_window_mac.mm
index 67565ab5cffb..2c0513ff0487 100644
--- a/shell/browser/native_window_mac.mm
+++ b/shell/browser/native_window_mac.mm
@@ -1117,6 +1117,8 @@ std::string NativeWindowMac::GetRepresentedFilename() {
 
 void NativeWindowMac::SetDocumentEdited(bool edited) {
   [window_ setDocumentEdited:edited];
+  if (buttons_proxy_)
+    [buttons_proxy_ redraw];
 }
 
 bool NativeWindowMac::IsDocumentEdited() {