diff --git a/shell/browser/native_window_mac.mm b/shell/browser/native_window_mac.mm
index d3d0152497d3b..e339366b05a2d 100644
--- a/shell/browser/native_window_mac.mm
+++ b/shell/browser/native_window_mac.mm
@@ -1692,6 +1692,9 @@ void ReorderChildWindowAbove(NSWindow* child_window, NSWindow* other_window) {
   // Restore the window title under fullscreen mode.
   if (buttons_proxy_)
     [window_ setTitleVisibility:NSWindowTitleVisible];
+
+  if (transparent() || !has_frame())
+    [window_ setTitlebarAppearsTransparent:NO];
 }
 
 void NativeWindowMac::NotifyWindowLeaveFullScreen() {
@@ -1701,6 +1704,9 @@ void ReorderChildWindowAbove(NSWindow* child_window, NSWindow* other_window) {
     [buttons_proxy_ redraw];
     [buttons_proxy_ setVisible:YES];
   }
+
+  if (transparent() || !has_frame())
+    [window_ setTitlebarAppearsTransparent:YES];
 }
 
 void NativeWindowMac::NotifyWindowWillEnterFullScreen() {