diff --git a/main/main.cpp b/main/main.cpp
index e371bef25fc..1c02fcf939c 100644
--- a/main/main.cpp
+++ b/main/main.cpp
@@ -1140,7 +1140,7 @@ Error Main::setup(const char *execpath, int argc, char *argv[], bool p_second_ph
 		}
 
 		if (bool(GLOBAL_GET("display/window/size/always_on_top"))) {
-			window_flags |= DisplayServer::WINDOW_FLAG_ALWAYS_ON_TOP;
+			window_flags |= DisplayServer::WINDOW_FLAG_ALWAYS_ON_TOP_BIT;
 		}
 	}
 
diff --git a/platform/osx/display_server_osx.mm b/platform/osx/display_server_osx.mm
index 3b829502245..c4a5849d43e 100644
--- a/platform/osx/display_server_osx.mm
+++ b/platform/osx/display_server_osx.mm
@@ -2374,7 +2374,11 @@ void DisplayServerOSX::_update_window(WindowData p_wd) {
 		[p_wd.window_object setHidesOnDeactivate:YES];
 	} else {
 		// Reset these when our window is not a borderless window that covers up the screen
-		[p_wd.window_object setLevel:NSNormalWindowLevel];
+		if (p_wd.on_top) {
+			[p_wd.window_object setLevel:NSFloatingWindowLevel];
+		} else {
+			[p_wd.window_object setLevel:NSNormalWindowLevel];
+		}
 		[p_wd.window_object setHidesOnDeactivate:NO];
 	}
 }