Update AppleID Settings - macOS Catalina

Worked for me. I noticed a message that stated my Apple ID password was not strong. Changed the password and the sign in issue appears to be resolved.

Signing out of iCloud and logging back in fixed the issue for me. Turning on iCloud keychain didn't work for me.

Finally worked. Signing out and then back in of iCloud on the affected device fixed the issues. Still...shame on Apple for not catching this.

While speaking with an Apple Tech about this problem, he had me sign out of iCloud and then sign back in, and that seems to have worked.

This was horrible. I had to enable the keychain like 5 times typing in both my Apple ID password then the Macs password. After several tries it finally prompted me for the password from a trusted device. Maybe so many users are setting up Catalina that the servers are kicking users back when trying to authenticate.

Right, I did the same. Then I signed out of iCloud on the "Overview" section in the "Apple ID" area of "Settings". Then signed back in and let it redo everything. Has worked ever since on my MacBook Pro 13 2017.

Tried many things:

change MacBook passward

reset keychain (delete reboot let Mac recreate it)

logout of iCloud

some of these worked but within 1 day the problem returned...

this may have worked:

problem was on my macbook

changed my appleID password on my phone...on Apple ID website

this caused my phone to ask me for passcode...etc

then my MacBook asked for verification from phone; asked for phone passcode...

seemed to work...well see if it sticks...

but it seemed to reset things pretty fundamentally

This seems to have worked for me. (To remove my macbook pro from appleid.apple.com, and resigning in). Keychain still isn't checked in the icloud preferences, but at least it isn't complaining. (So far)

If this helps anyone. What I did is on my iPhone I went to settings, clicked on the top where it says your name and deleted MacBook Air as a device associated with my account . Restart your Mac and login then it asks for a code! Hopefully it works for any of y’all.

Had same problem. I logged out of iCloud completely and then back in. Resolved.

I had the same problem and went through the steps of the keychain mentioned above but this was the solution for me. I had to re-set my Apple ID password and then it worked.

I ran into this issue in the beta on an iMac but I created a new user profile and it wasn't affected. I assumed it was a glitch in the upgrade from Mojave to the Catalina Beta. During beta I also ran into an issue that if I logged out of my Apple ID I could not get iCloud Drive to work with desktop and documents folders until I created the new user profile.

Hello My frustrated Mac friends ... so apple is issue can't sign no iCloud etc .... this has happened because you failed to set up id correctly.. you may think you have but if you can't access and are stuck in the iCloud loop then you didn't ..

Fix: Go to System Preferences - User & Groups - Create new user(admin right if you need) -save log out of existing user and log into new user .... this will take you though a new User setup - do not skip the Apple ID .. entering you Apple ID and password once is all it should take to activate all apple logins... if you skip this you will once again be in a loop and must repeat

I fixed this several weeks ago by calling Apple support. They walked me through the process which essentially was just signing out from my Apple cloud account and then signing back in. It disappeared on both my MacBooks. I am unsure whether I could do this again on my own. I do agree that this should not have been an issue in the first release and subsequent updates. Just call support, the more complaints they get will get the point across.

Hi michaeljohn920!

I had to retry the process of ticking the iCloud Keychain several times before it eventually asked me to enter the passcode from another trusted device.