I tried searching for this, but was inundated with "Outlook keeps asking for prompt" results.
I have Exchange Server 2003. Just joined an off-site location to our VPN, and changed all the users from POP accounts to Exchange accounts. (It's a situation with multiple users using a shared login, so I have a separate Outlook profile set for each user.) Deleted the POP accounts after importing all the old emails into the Exchange accounts.
First problem is that when you open Outlook, you're prompted to choose a profile, and when you choose a profile, that profile's email opens up right away, AND you're prompted for a password. If you just cancel out of the prompt, you're still in the email account. In the account settings, under More Settings/Security, I have the "Always prompt for logon credentials" option checked.
This is happening at three different locations, and I'm not sure why. Any help would be greatly appreciated.