MDM iOS devices timeout during automatic configuration

MDM iOS devices timeout during automatic configuration

Everything looks good on the DEP side. It's showing that it is connected to the DesktopCentral server and the devices enrolled in DEP are showing up on the MDM DEP page. After I assign a user and the device status is updated to "Awaiting Device Activation" I turn on the device and it attempts automatic configuration but gives a timeout error. This process is all fairly new to me, any ideas on where it is failing and what I should check?
                New to ADManager Plus?

                  New to ADSelfService Plus?