The messages that then show up in the user-debug would seem to indicate that the devices falls back into the default VLAN for the controller itself (the vlan we use to manage the controller and AP). Then after a short period of time the device takes a default IP of 192.168.254.254.
So after looking at the user-debug, it looks like initially everything goes fine, the user gets back the VSA from the ClearPass and the user role and vlan are switched accordingly, but still no IP.