Outlook Anywhere with Exchange 2007 on Windows Server 2008
Outlook Anywhere / Outlook Autodiscovery on Windows 2008 still has some problems.
Read this most excellent post that has all the details.
Long story shorts: Modify the hosts file, remove the IPv6 localhost (::1) and then add hosts entries for your server. I would recommend against disabling IPv6 on the Exchange server, as this is probably not a recommended or supported configuration.
The root cause is that Outlook 2007 can’t contact a DC/Domain Controller using RPC over HTTP/Outlook Anywhere when used on Windows Server 2008.
Also note that NTLM Authentification for Outlook 2007/Outlook Anywhere is broken on Windows Server 2008.

John Smiths:
Hello, Windows is not a real server. It doesn’t work on any mainframe intended for the real servers. So why do you expand this well paid M$ lying? I suggest to read about M$IE8 in order you’d like to get the facts. [URL removed]
25. May, 2008, 19:14Lukas Beeler:
John,
Sit back, relax, have a beer. It’s just software.
25. May, 2008, 19:25