Your comments

Do these specific Guest machines have anything in common?  Are they all offline often?

Also, within the web.config on the ConnectWise Control server, to what value is the setting "AccessSessionExpireSeconds" set?

From an implementation point of view I don't see a bug with this but rather a feature request.  If a User has access to control their own groups/roles within an Active Directory then they are basically Administrators within that IdP.

Which IdentityProvider have you integrated into ConnectWise Control for SAML?

Thanks for the report, I was able to replicate the behavior and I have registered it as a defect.

A separate issue was found in 6.5 and 6.6 with very similar results where upon connection to some Mac Guests the screen is black and you are unable to wake up the machine.  This has been fixed in 6.7.

A potential workaround for this scenarios is to disconnect from the remote machine and execute the following command  (via the Commands tab on the Host page):

/usr/bin/caffeinate -u -t 1

And then reconnect to it.