I have a user running Windows 7 Pro. We recently replaced their existing server and moved them from win2k3 SBS to Win2k8 SBS. All the computers in the office are working fine except hers. What's strange is after several minutes or so (time not set in stone) Outlook will prompt her to log in again. When she does, it does not allow her to log in. I have to go into AD manually and Unlock her account to get her to login.
There is a known issue with SBS2008.
There are a few things you can try and I have documented them in my article here: http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/A_2300-Outlook-continually-prompting-for-username-and-password.html
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The email signature template has been downloaded from: