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Windows 7 Not Remembering On-Top Elements

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I used to have a triple-monitor setup, but one of the monitors died. Since I removed the other monitor, Windows has had trouble remembering the "Always On Top" status for: 1) The Taskbar 2) Gadgets and 3) Winamp.

I've restarted a number of times since I removed the monitor but still the problem persists. Windows will remember to keep an element on top for a little while, but eventually forgets until I manually click on the object to bring it back on top, where it remains until Windows next forgets. The taskbar no longer has a tickbox option for "Always on top". Winamp is set to be "Always On Top".

Does anyone have any ideas on how to resolve this problem? Thanks!

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