1. Server is an Windows Server 2008 R2 with Exchange Server 2010 running. OWA and Outlook Anywhere are enabled. It's configured to be accessable from outside via http(s)://outlook.companyname.com
2. Client is a new off-site Windows 7 client with Outlook 2010 installed.
3. User XYZ is enabled to use OWA and Outlook Anywhere and used both successfully on an old computer already.
Now my question is: is it possible to have the Outlook configured off-site without having the user XYZ come here or logging in to a VPN? It seems that for the first-use Outlook "New account" configuration assistant, Outlook Anywhere via HTTP/S is not usable, but you need to have a direct connection to the network first with classic connectivity - be it having him here physically here in our network or be it logged in via a VPN first. Otherwise "User is not in the address list" and asking for username/password (which are then rejected) and similar errors come up.
Thanks in advance for any help. If you require any more sys information, just let me know.