diff --git a/src/lib/platform/MSWindowsScreen.cpp b/src/lib/platform/MSWindowsScreen.cpp
index 6bd2f24d..68379df9 100644
--- a/src/lib/platform/MSWindowsScreen.cpp
+++ b/src/lib/platform/MSWindowsScreen.cpp
@@ -1878,6 +1878,7 @@ std::string& MSWindowsScreen::getDraggingFilename()
             SWP_SHOWWINDOW);
 
         // TODO: fake these keys properly
+        ARCH->sleep(.05f); // A tiny sleep here makes the DragEnter event on m_dropWindow trigger much more consistently
         fakeKeyDown(kKeyEscape, 8192, 1);
         fakeKeyUp(1);
         fakeMouseButton(kButtonLeft, false);