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Outlook prompts you for a password the first time you check mail and everytime you reopen it. Under user properties --if there is no check in remeber password then the password is grayed out. if the check is there it remebers a blank password and you need to enter one everytime you open outlook...it remebers it till the next time you open outlook...any ideas
 

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you may try to uninstall/reinstall Outlook.. back up your email first though it sounds like something in the registry may be corrupt.
 
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