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I think your problem comes from the fact that you are trying to remove a popup with the PopUpManager.remove(this) from inside the window itself. If I am not mistaking, you should handle close events from the main app.
Hope this does the trick!
Thanks all for the replies. My problem turned out having to do with incorrectly setting the parent of the popup window.
In BrokenPopup.as, dragDropHandler(), instead of using the PopUpManager I ended up adding the new BrokenPopupComponent object as a child of the containing Canvas object identified as "popupCanvas" in BrokenPopup.mxml. Not sure why the original implementation didn't work correctly, but I did want the popup to be a child of the Canvas and PopUpManager doesn't appear to support this.
Again,thanks for the replies.