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I have a SBS2011 server with an internal domain name: mydomain.local.

The external address is different:

When connected over the VPN, if a user opens Outlook, it will prompt for a username and password.

The username is already set to their email address:

However, this is incorrect, as their username should be: mydomain\username.

Even if we tick Remember Password, the next time Outlook is opened over the VPN, the credentials are asked for, and the username is set incorrectly as the email address.

What are the reasons for this and is there anyway to prevent this confusion as users seem to be unable to remember this difference between domain username and email address?

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To be completely unhelpful, but somewhat serious, is getting smarter users an option? I ask because that would solve a number of my current issues as well... – HopelessN00b Aug 30 '12 at 16:02
up vote 1 down vote accepted

Try to manually add the credentials to the credential manager in the control panel and remove any other credentials to that server/connection.

When connected to the VPN are they on a domain joined PC or is it just a workstation (no domain ties) connecting to the VPN?

Also their username could be if that's what the user principal name is set to..check it in Exchange Shell

Get-Mailbox "username" | fl UserPrincipalName

When connecting via VPN are you connecting to MAPI or Outlook anywhere? If you're not using NTLM authentication for Outlook Anywhere then you will always get prompted for the password.

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