Jamf Connect Menu bar app not auto logging in

[mrcw]

Hi,

We are trying to complete our setup for deployment of Mac devices which including Jamf Connect and for some reason all of a sudden when we do a unbox and our MDM (Intune) installs Jamf Connect the menu bar app is prompting for the login of the user where it used to pass the login info from the Jamf Connect Login. 

If the user does not sign into that window it never seems to connect even after a reboot it just keeps prompting and you can close the window so the password syncs are never occurring.

If another user logs into the MacBook and the new user profile is created it automatically connects the accounts, but the first time user account never gets connected unless they login. 

I'm not sure what has changed for this to occur, anyone else experienced this?

We are using Jamf Connect 2.21.

[AJPinto]

This screams something is wrong with how you are deploying the configuration profiles. When the 1st user is having issues, have you confirmed that the menu bar configuration profile is on the Mac?

Just to ask, does it matter who "Person 1" and "Person 2" are? In other words if you flipped the log in order of person 1 and person 2 (person 2 logging in first), would it work for person 1?