Issue Description
Once the admin initiate Start Session, it will just load and then it will timeout. This error does not occur if iBoss is disabled.
iBoss VPN was blocking service hosted on socket.us.jra.services.jamfcloud.com and directing it to an "Action" Called "DOH" which applied more encryption to this service host causing the session to time out.
Troubleshooting Steps
iBoss team was able to safe list the service hosted on socket.us.jra.services.jamfcloud.com and update the policy on iBoss.