diff --git a/platform/macos/display_server_macos.h b/platform/macos/display_server_macos.h
index 9f1f7d21e2..9519ca5270 100644
--- a/platform/macos/display_server_macos.h
+++ b/platform/macos/display_server_macos.h
@@ -216,7 +216,7 @@ private:
 	Callable system_theme_changed;
 
 	WindowID _create_window(WindowMode p_mode, VSyncMode p_vsync_mode, const Rect2i &p_rect);
-	void _update_window_style(WindowData p_wd);
+	void _update_window_style(WindowData p_wd, WindowID p_window);
 
 	void _update_displays_arrangement() const;
 	Point2i _get_native_screen_position(int p_screen) const;
@@ -266,6 +266,8 @@ public:
 	void mouse_exit_window(WindowID p_window);
 	void update_presentation_mode();
 
+	bool is_always_on_top_recursive(WindowID p_window) const;
+
 	void window_destroy(WindowID p_window);
 	void window_resize(WindowID p_window, int p_width, int p_height);
 	void window_set_custom_window_buttons(WindowData &p_wd, bool p_enabled);
diff --git a/platform/macos/display_server_macos.mm b/platform/macos/display_server_macos.mm
index 472d54ae62..ee9692f5d7 100644
--- a/platform/macos/display_server_macos.mm
+++ b/platform/macos/display_server_macos.mm
@@ -213,7 +213,7 @@ DisplayServerMacOS::WindowID DisplayServerMacOS::_create_window(WindowMode p_mod
 	return id;
 }
 
-void DisplayServerMacOS::_update_window_style(WindowData p_wd) {
+void DisplayServerMacOS::_update_window_style(WindowData p_wd, WindowID p_window) {
 	bool borderless_full = false;
 
 	if (p_wd.borderless) {
@@ -233,7 +233,7 @@ void DisplayServerMacOS::_update_window_style(WindowData p_wd) {
 		[(NSWindow *)p_wd.window_object setHidesOnDeactivate:YES];
 	} else {
 		// Reset these when our window is not a borderless window that covers up the screen.
-		if (p_wd.on_top && !p_wd.fullscreen) {
+		if (is_always_on_top_recursive(p_window) && !p_wd.fullscreen) {
 			[(NSWindow *)p_wd.window_object setLevel:NSFloatingWindowLevel];
 		} else {
 			[(NSWindow *)p_wd.window_object setLevel:NSNormalWindowLevel];
@@ -242,6 +242,21 @@ void DisplayServerMacOS::_update_window_style(WindowData p_wd) {
 	}
 }
 
+bool DisplayServerMacOS::is_always_on_top_recursive(WindowID p_window) const {
+	ERR_FAIL_COND_V(!windows.has(p_window), false);
+
+	const WindowData &wd = windows[p_window];
+	if (wd.on_top) {
+		return true;
+	}
+
+	if (wd.transient_parent != INVALID_WINDOW_ID) {
+		return is_always_on_top_recursive(wd.transient_parent);
+	}
+
+	return false;
+}
+
 void DisplayServerMacOS::set_window_per_pixel_transparency_enabled(bool p_enabled, WindowID p_window) {
 	ERR_FAIL_COND(!windows.has(p_window));
 	WindowData &wd = windows[p_window];
@@ -2112,7 +2127,7 @@ void DisplayServerMacOS::window_set_position(const Point2i &p_position, WindowID
 
 	[wd.window_object setFrameTopLeftPoint:NSMakePoint(position.x - offset.x, position.y - offset.y)];
 
-	_update_window_style(wd);
+	_update_window_style(wd, p_window);
 	update_mouse_pos(wd, [wd.window_object mouseLocationOutsideOfEventStream]);
 }
 
@@ -2250,7 +2265,7 @@ void DisplayServerMacOS::window_set_size(const Size2i p_size, WindowID p_window)
 
 	[wd.window_object setFrame:new_frame display:YES];
 
-	_update_window_style(wd);
+	_update_window_style(wd, p_window);
 }
 
 Size2i DisplayServerMacOS::window_get_size(WindowID p_window) const {
@@ -2547,7 +2562,7 @@ void DisplayServerMacOS::window_set_flag(WindowFlags p_flag, bool p_enabled, Win
 				[wd.window_object setFrame:NSMakeRect(frameRect.origin.x, frameRect.origin.y, frameRect.size.width + 1, frameRect.size.height) display:NO];
 				[wd.window_object setFrame:frameRect display:NO];
 			}
-			_update_window_style(wd);
+			_update_window_style(wd, p_window);
 			if (was_visible || [wd.window_object isVisible]) {
 				if ([wd.window_object isMiniaturized]) {
 					return;
@@ -2632,11 +2647,7 @@ bool DisplayServerMacOS::window_get_flag(WindowFlags p_flag, WindowID p_window)
 			return [wd.window_object styleMask] == NSWindowStyleMaskBorderless;
 		} break;
 		case WINDOW_FLAG_ALWAYS_ON_TOP: {
-			if (wd.fullscreen) {
-				return wd.on_top;
-			} else {
-				return [(NSWindow *)wd.window_object level] == NSFloatingWindowLevel;
-			}
+			return wd.on_top;
 		} break;
 		case WINDOW_FLAG_TRANSPARENT: {
 			return wd.layered_window;
diff --git a/platform/macos/godot_window_delegate.mm b/platform/macos/godot_window_delegate.mm
index 7749debfd6..35c053dca5 100644
--- a/platform/macos/godot_window_delegate.mm
+++ b/platform/macos/godot_window_delegate.mm
@@ -194,7 +194,7 @@
 	}
 
 	// Restore on-top state.
-	if (wd.on_top) {
+	if (ds->is_always_on_top_recursive(window_id)) {
 		[wd.window_object setLevel:NSFloatingWindowLevel];
 	}
 
diff --git a/platform/windows/display_server_windows.cpp b/platform/windows/display_server_windows.cpp
index 0769603d8e..a0d1054933 100644
--- a/platform/windows/display_server_windows.cpp
+++ b/platform/windows/display_server_windows.cpp
@@ -1606,6 +1606,21 @@ DisplayServer::WindowID DisplayServerWindows::create_sub_window(WindowMode p_mod
 	return window_id;
 }
 
+bool DisplayServerWindows::_is_always_on_top_recursive(WindowID p_window) const {
+	ERR_FAIL_COND_V(!windows.has(p_window), false);
+
+	const WindowData &wd = windows[p_window];
+	if (wd.always_on_top) {
+		return true;
+	}
+
+	if (wd.transient_parent != INVALID_WINDOW_ID) {
+		return _is_always_on_top_recursive(wd.transient_parent);
+	}
+
+	return false;
+}
+
 void DisplayServerWindows::show_window(WindowID p_id) {
 	ERR_FAIL_COND(!windows.has(p_id));
 
@@ -1633,7 +1648,7 @@ void DisplayServerWindows::show_window(WindowID p_id) {
 		SetForegroundWindow(wd.hWnd); // Slightly higher priority.
 		SetFocus(wd.hWnd); // Set keyboard focus.
 	}
-	if (wd.always_on_top) {
+	if (_is_always_on_top_recursive(p_id)) {
 		SetWindowPos(wd.hWnd, HWND_TOPMOST, 0, 0, 0, 0, SWP_FRAMECHANGED | SWP_NOMOVE | SWP_NOSIZE | ((wd.no_focus || wd.is_popup) ? SWP_NOACTIVATE : 0));
 	}
 }
@@ -2256,7 +2271,7 @@ void DisplayServerWindows::_update_window_style(WindowID p_window, bool p_repain
 		set_icon(icon);
 	}
 
-	SetWindowPos(wd.hWnd, wd.always_on_top ? HWND_TOPMOST : HWND_NOTOPMOST, 0, 0, 0, 0, SWP_FRAMECHANGED | SWP_NOMOVE | SWP_NOSIZE | ((wd.no_focus || wd.is_popup) ? SWP_NOACTIVATE : 0));
+	SetWindowPos(wd.hWnd, _is_always_on_top_recursive(p_window) ? HWND_TOPMOST : HWND_NOTOPMOST, 0, 0, 0, 0, SWP_FRAMECHANGED | SWP_NOMOVE | SWP_NOSIZE | ((wd.no_focus || wd.is_popup) ? SWP_NOACTIVATE : 0));
 
 	if (p_repaint) {
 		RECT rect;
diff --git a/platform/windows/display_server_windows.h b/platform/windows/display_server_windows.h
index af5243a149..52a180984b 100644
--- a/platform/windows/display_server_windows.h
+++ b/platform/windows/display_server_windows.h
@@ -635,6 +635,8 @@ class DisplayServerWindows : public DisplayServer {
 	void _drag_event(WindowID p_window, float p_x, float p_y, int idx);
 	void _touch_event(WindowID p_window, bool p_pressed, float p_x, float p_y, int idx);
 
+	bool _is_always_on_top_recursive(WindowID p_window) const;
+
 	void _update_window_style(WindowID p_window, bool p_repaint = true);
 	void _update_window_mouse_passthrough(WindowID p_window);