We have two iPad that we purchased and are eligible for DEP.
I have not yet made a pre-stage enrollment for these devices.
They have already been turned on and are being used.
If they are enrolled by the user through the web, and did not come through a DEP pre-stage .... would they be supervised or unsupervised?
They will be unsupervised. But if I remember right, I think you can get them to be supervised by creating a enrollment profile in the JSS, exporting it, opening it with Configurator 2, and connecting the iPad.
Maybe this page can help?