Just wanted to write this up for anyone else in the future.
After deploying Endpoint to many machines we started noticing that we couldn't activate Windows 7 / Office anymore. The error was pretty obvious about it being a connectivity issue with Websense. Found it was trying to go to https://activation.sls.microsoft.com so I added "activation.sls.microsoft.com" into the SSL Decryption Bypass list and that fixed our problem.