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I would like to have it so that if the system is rebooted, it auto logs back in to a particular user name so that certain applications can be run under that username. Is this possible to do?

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I dont know if this works on Windows Server 2008 but here is technet kb article with instructions how to do it for windows 2003.

Remember, this is a serious security risk to I dont recommend you do this in the first place. If you must do this, the screen saver to 1 minute and enable "on resume, password protect"

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