The dialog is probably not HTML, that's why it won't spy. Here's a trick to try. Beforehand make sure IE is not maximised. Then when the pop-up is displayed, drag it so that it overhangs the edge of the main IE window. Then use Win32 mode to spy the pop-up. Sometimes Win32 mode cannot soy a dialog when it is contained within the main IE window, but just by pushing the dialog past the edge of the window you can spy it. Once captured, the Win32 element will work even if the dialog is within the main window, this trick is only to enable the initial spying.