I'm not sure, it could have to do with authentication? What type of authentication are you using? SAML, AD, Kerberos, impersonation, etc?
Also, what happens when you hit YES.
Hi Jeff thanks for your reply.
I think I've figured it out. It seems like the issue has something to do with the 'Guest User' option. Guest User The Guest user access is enabled by default when our server is re-installed with core-based/unlimited licenses. When I manually checked it off all problems seemed to go away.