Basically this is what happened:
The MSDN subscriptions version of
Windows Server 2008 installs by default using KMS (Key Management
Service).
The key MSDN gave is a MAK (Multiple Activation Key).
So the
install does not use the key, it tries to talk to KMS.
We don't have KMS here
so it fails.
Doing the following activates it using the MAK
key:
1) Open a cmd shell as Administrator.
2) Type the following (but
use your key instead of all the X's)
slmgr -ipk
XXXXX-XXXXX-XXXXX-XXXXX-XXXXX
3) The prompt will return right away, but
there is a licensing task that it started (if you look in Task Manager you can
find a task SLsvc using up cpu, I assume this is where the licensing is going
on).
4) After a while a dialog will pop up saying that it has been
activated.
Good Luck
above was lifted from a forum post. buried in there is the command line to
bypass KMS and use the proper MAK instead. It worked!
In the process of figuring this out, MSFT had me download a video explaining
how to setup a KMS, one of the requirements is that you need 5 servers to
contact KMS before it will work. That's fucking retarded. If I'm paying for a
product, I expect that I'm paying for ease of use. Making your
paying customers bend over backwards to use the product you are selling is
unsustainable, bad business. You can do better than that,
Microsoft.