Update AppleID Settings - macOS Catalina

This worked for me, but only after I logged out and back in.

Quickest way to solve this is to completely sign out of AppleID on your Macbook and sign back in.

I guess I didn't wait long enough. I ended up going to a movie and a few hours later when I came back home it had finally logged on and even after a reboot all looks good so far.

I'm having the same problem, having just installed Catalina. I enter the Apple ID password, it prompts (after about 10 seconds) for the local Mac account password, then the badge/triangle is cleared - for about 5 minutes. Then it comes back and asks for the same info. This repeats indefinitely.

Enabling iCloud Keychain didn't help at all in this case. The Catalina macbook is still prompting for credentials. And every time I enter them (including here on the communities) I'm no longer getting a 2FA prompt anywhere on any device.

I've got this same problem

"Enabling iCloud Keychain didn't help at all in this case. The Catalina macbook is still prompting for credentials. And every time I enter them (including here on the communities) I'm no longer getting a 2FA prompt anywhere on any device."

So it appears that none of the solutions here are permanent. Signing out and back in to Apple ID, Toggling the Keychain and Resetting the Apple ID password all only provide a temporary connections. Within a few mins to an hour, the system resets itself back to a system alert notification that asks you to update your Apple ID again. These suggested fixes do work, but only temporarily!! 

Obviously Apple Support doesn't know how to fix this yet either and are closely watching the discussion  threads. This is a deep software issue and a huge bug that should have been caught.

Other threads seem to have the most succsess with the "logging out of Apple ID then Logging back in" method. It seems “resetting the password” and or “toggling the keychain” are not stable or consistent solutions for most users.

Thanks for the tip. In my case, it took an hour or two for the issue to go away after multiple requests to re-enter my Apple ID pw and Mac pw...until eventually, my Mac requested my iPhone lock screen password to complete the process. All good now (finally)!

Has the same problem on my Mac Pro Catalina installation. Apple may have corrected a sever bug as I was able to clear the AppleID flag and get all functions including keychain working by putting in my iCloud password and User password this morning after 2 attempts. All services are working now including iCloud Keychain.

The issue would seem to be related to the process used when setting up the Mac initially with the Apple ID. Maybe do the fresh install and do not log in at all with the Apple ID at all during the setup. Wait to do that once the Mac is up and running fully. Then it will go through the Apple ID joining and setup things but not be while the initial account was being setup.

I got the prompt to update iCloud that would never resolve. I was unable to sign out of iCloud. I was unable to check keychain. I changed my iCloud password. Nothing worked. This, in addition to horrendous networking issues preventing communication with other computers.

MY SOLUTION: I restored a backup of Mojave and now all is well!

I've been a happy Mac user for 5 years and until Catalina every OS update has been smooth and problem free, even early releases. In this case I'm going to wait a few months before giving Catalina another shot.

I'm having the same issue. I tried what you said Michael and it didn't work. My keychain was not checked so I checked it and it asked me to enter my apple ID password a couple times and also my macbook password and then it finally checked the box but a short while later it asked me for my apple ID again. Then I decided to check to see if Keychain was still checked and it wasn't checked anymore. No clue what is going on. I tried checking the Keychain box again and entering my password again and it just keeps asking for my apple ID

Having the same problem but in addition, when I try the suggested solution, it won't complete "setting up" the keychain after I click on it.

Restarted iMac and tried the keychain fix again. Finally asked for iPhone passcode. This is messed up.