diff --git a/Userland/Services/WindowServer/Compositor.cpp b/Userland/Services/WindowServer/Compositor.cpp
index d41c656355..59aa87780d 100644
--- a/Userland/Services/WindowServer/Compositor.cpp
+++ b/Userland/Services/WindowServer/Compositor.cpp
@@ -857,7 +857,7 @@ Gfx::IntRect Compositor::current_cursor_rect() const
 
 void Compositor::invalidate_cursor(bool compose_immediately)
 {
-    if (m_invalidated_cursor)
+    if (m_invalidated_cursor && !compose_immediately)
         return;
     m_invalidated_cursor = true;
     m_invalidated_any = true;
diff --git a/Userland/Services/WindowServer/WindowManager.cpp b/Userland/Services/WindowServer/WindowManager.cpp
index f3359c8b27..ef2614269e 100644
--- a/Userland/Services/WindowServer/WindowManager.cpp
+++ b/Userland/Services/WindowServer/WindowManager.cpp
@@ -2081,10 +2081,10 @@ void WindowManager::start_dnd_drag(ConnectionFromClient& client, String const& t
     VERIFY(!m_dnd_client);
     m_dnd_client = client;
     m_dnd_text = text;
+    Compositor::the().invalidate_cursor(true);
     m_dnd_overlay = Compositor::the().create_overlay<DndOverlay>(text, bitmap);
     m_dnd_overlay->set_enabled(true);
     m_dnd_mime_data = mime_data;
-    Compositor::the().invalidate_cursor();
     set_automatic_cursor_tracking_window(nullptr);
 }