How to stop Catalina from continually telling me I need to sign in again? Ugraded to Catalina 10.15. The doc shows a little notification icon above the System Preferences App



Opening the System Preferences shows this



So I click continue which gives me this



So I click continue which brings me here



I enter my password. About 7 seconds later the notification disppears



But 5 seconds after that this appears



Everything seems fine but then 15 seconds later the notification at the top appears again. Have repeated 4 times now. This happens on both my Macs

How do I fix this so it stops asking?
If signing in several times doesn’t resolve this and you can’t or won’t wait it out, signing out completely appears to get this prompt to go away. 


iCloud Keychain refuses to setup on Catalina


You do of course have to deal with the side effects of signing out like choosing to delete or keep local copies of iCloud data and then setting up your iCloud preferences and settings. 

If you have a good backup, you could also try force quitting the system preferences app before you log out of the account.