I have a couple of servers on Standard 2012R2 (a Domain Controller & File Server) virtualized on VMWare ESXi 5.1.  Server Manager tells me that they have never checked or updated (although they show 40 updates applied).  Set to download updates and notify for installation.  I've manually triggered to check for updates.  The "Windows Update" window sits there with the 'Checking for updates.." and the progress bar scrolls by ad infinitum.  I've let it run all night and still nothing.  All my other VM installations are updating fine.  I've spent a month building this new domain for the new company being created and so not in full production yet, but I still don't want to re-create the servers.

Anyone else have this issue and fix it?

You might check the system and Windows Update event logs.

Event Viewer\Applications\Microsoft\Windows\WindowsUpdateClient\Operational

Hi,

How did you configure your DNS? Is it able to resolve external name?

In addition, you can check windowsupdate.log which records WU agent behavior.