This Mac can't connect to iCloud

Hello,

I am getting this pop up almost every time I log in to my user account (2014 MacBook Air 13")

The first time or two that it takes me to iCloud Preferences, I enter the password (you can't hit ENTER like normal, you have to actually click the button) and it pops back up. Only on the second or third try, most times, does it not pop back up again.

I don't see this on my iOS devices.

Any suggestions?

Thanks,

Michael