The new setting is for silent checkout of the device to the logged in user. What version of UEM are you on?
This seems to do be checkout in which the user needs to sign into Hub to check the device out. Possibly because the authentication times out it fails.
So one reason could be a network issue during auth, are you sure the devices can reach UEM, Access and Google to go through the authentication flow? Any proxy or firewall that could block any of the required connections?
Second could be timeout of the authentication session itself at either Google or Access and failed auth because of that.
I would check the local Hub logs, the Access audit logs for the time and user(might not show as no succesful auth) and Google sign in logs.
If there is a timeout in authentication there should be failed attempts in the Access audit logs, potentially in the backend logs if it couldn't correlate the authentication request send to Google and the late return of the authentication.