Sorry for the late reply.
It turns out that bitlocker encryption would only take effect when I connected to the same network as our KSC server.
As it stands, I'm in a remote office and while our KSC does have a public IP, it wouldn't apply over the public IP or when connected via SSL VPN. I went to visit the main office and it applied almost as soon as I connected to that network.
I don't know if that's a bug or a feature.