I've only noticed this as default behaviour under Vista. To prevent it from removing Start Menu items after a given amount of time (I don't know what the time out value is or how to change it), edit or create the following registry key to the given value:
HKEY_CURRENT_USER\Software\Microsoft\Windows\CurrentVersion\Explorer\Advanced
DWORD, StartMenuInit: 3
Prevent Start Menu items from disappearing.
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Re: Prevent Start Menu items from disappearing.
I had thought this would work - but it doesn't. Start Menu items are still disappearing on me. This is one of the more annoying issues I've encountered with Vista.