diff --git a/dlls/winemac.drv/cocoa_window.m b/dlls/winemac.drv/cocoa_window.m
index f68a37cbead..141fc61d508 100644
--- a/dlls/winemac.drv/cocoa_window.m
+++ b/dlls/winemac.drv/cocoa_window.m
@@ -949,7 +949,8 @@ - (BOOL) setFrameIfOnScreen:(NSRect)contentRect
 
     - (void) setMacDrvParentWindow:(WineWindow*)parent
     {
-        if ([self parentWindow] != parent)
+        WineWindow* oldParent = (WineWindow*)[self parentWindow];
+        if ((oldParent && oldParent != parent) || (!oldParent && latentParentWindow != parent))
         {
             [[self parentWindow] removeChildWindow:self];
             self.latentParentWindow = nil;