I'm using Windows 7's "combine [buttons] when taskbar is full" option, so programs I'm running might each have only one button on the taskbar even when they have multiple windows open. Hovering over one of those buttons brings up a flyout menu that lists the program's windows. Here's an example using MS Outlook:
I like the fact that I can close windows directly from the flyout by using the little red X button that appears by the window preview on hover (for an example, see the second item in the flyout above).
However, once I close one window, the flyout disappears, and I have to open it again if I want to close another window. How can I make the flyout remain active after I close one of the windows it contains, so that I can quickly close several windows in a row?