Ok, our issue ended up being an issue with the gateway and outbound traffic. Make sure the gateway can get outbound to do http/https requests. It needs to do this for categorization.
Once we fixed this, we were quickly online and https inspecting for a few test workstations.
Interesting enough, once we turned it on for the testing hosts, we also some issues with other hosts that we also had to put an override in place for. This traffic went over a VPN and was NOT internet bound so did not match the policy for bypass.