Windows Update seems to break authentication

Question

We have several production servers with 2012r2 installed and have noticed in the last couple of days that they are reporting that they need to be authenticated. These are all open license Server 2012r2 standard. When trying to authenticate the license we get an error that says the license is invalid. When contacting MS support they verify that the key is correct and authentic but it still won't activate. Now we are told we must purchase Software Assurance for Microsoft to check into this problem at a cost of $499 per incident. Has anyone else run into this problem and is there a solution? So far we've been on the phone for 1.5 hours.

Answer 1

1. Just to get it out of the way, licensing problems are off-topic. This is technically about activation, not licensing per se so is probably OK. Point is that only Microsoft can really help you.
2. You don't say what sort of license key you've used on these installs. Have you checked in the VLSC that these aren't Multiple Activation Keys that have been used too many times?
3. If all else fails you can almost certainly use telephone activation to activate your servers. Launch C:\Windows\System32\telephoneactivation.exe and follow the prompts. It's laborious (involves typing a 63 digit string into the phone and then another string into the activation wizard) but should work.