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)


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.