I’ve seen some weird activation issues in MS products with error codes that threw me off.

As i tried to activate Windows Server it said;

• A problem occurred when Windows tried to activate. Error Code 0x8004FE2F

With the Office 365 activation it said (in dutch);

• helaas, deze functie is uitgeschakeld door uw beheerder

I can only assume what this error is in english, but i suspect something like in kb2745026 or kb2853971

• This feature has been disabled by your administrator.
• We are unable to connect right now. Please check your network and try again later.
  Sorry, we can’t connect to your account. Please try again later.
• The installation fails and you receive the following error message:
  Something went wrong Error Code: 30174-4
• We’re sorry, something went wrong and we can’t do this for you right now. Please try again later. (0x8004FC12)

In this case the customer was using a UTM and had the web protection (=proxy) set to transparent.

This means the UTM is set as a gateway and proxies all traffic on ports 80/443, but is decrypts/encrypts all SSL traffic, which is something the MS products activation probably does not allow without using the proxy settings in Windows.

I mean to investigate the issue further, but for now i’m a bit pressed for time so i thought to just give the answer and look for the root cause a different time. Btw, i was looking in the proxy logs but they don’t show anything usefull.

The solution in this case was simple: setting the internet options to use a proxy was sufficient and after that, the MS products activated;