Connect to Internet and Aftermarket Radio Issues

Working with a 1998 Cherokee XJ 4.0. All firmware and software is updated. Tried two separate PC's without success. Everything electrical is stock except the stereo.

I am having two issues here.

The first is that I have an aftermarket stereo installed, and even after completely disconnecting it I still get the popup regarding aftermarket stereo's. Maybe its just a generalized notice, I have no clue.

The second issue is that both PC's are connected to the internet but the software keeps stating I need to connect to the internet. Maybe this too is just a generalized notice.

Upon reading the system the software keeps failing with baud rate: timed out error.