I have a new Windows 2008 SBS server installation that during testing was working perfectly. We have a mix of user in Windows XP and Windows 7. There are some users that access Exchange Mailbox using Outlook 2003 and other that access it using Outlook 2010.
During configuration testing and prep everything was working perfectly. We went live and the very next day, users that were accessing the system using the Outlook 2010 client started getting prompted for the password each and everytime they went into Outlook. As long as they remained in the program, it seemed to be ok.
We are running SP1 on Exchange 2007. I have installed a certificate from Godaddy.com for the following:
I post this message originally with the Certificate warning issue that would also pop up. But after installing the certificate the warning went away, but users still were being prompted for the login and password. We then rebooted the server on Friday around 11am and the login problem went away. This morning at around 12:30 pm, a user who had Outlook open, but not using it, started getting the security warning and was prompted for a login and password. The certificate warning has not resurfaced.
This Problem DOES NOT occur with our Outlook 2003 clients. They are not required to re-enter their password nor are they presented with a certificate warning.