Update AppleID Settings - macOS Catalina

Hi, got this problem too. Talked to Apple support, they just got me to sign out of iCloud on my Mac, then sign back in. Seemed to have solved it. I played around with keychain & changed my password as discussed below and those didn't work. The lady at Apple just said it was because my Mac wasn't communicating properly with the server, signing out & then back in forces it to communicate properly.

Only thing that worked for me was signing out and back in. On both my old Mac and my new one. I hated it both times, because I have lots of GB in my iCloud Drive :( And it also f*ed with my iTunes library (songs were in my iCloud Drive and I ended up with duplicates from my iCloud Music Library)

Same problem here. I noticed I was never prompted for a code to input as I have two-factor verification. If you have two-factor verification turned on already, this might be the issue. Try going to appleid.apple.com, log in and remove your mac device from the account from there. Reset your mac, and try again. You probably should do one device at a time so that you can receive the code in the first place. I just tried this and it apparently has solved my issues.

Oddly it wasn't letting me sign out from my mac. So I had to try this and I feel this way is better anyways because at least you don't have to delete or reload any of your photos or documents when it warns you about it. Good luck to all.

Yay finally the Apple ID continuous loop is fixed. As a new MacOS convert I was about to end it all and just reset my MacBook. Thanks WilliamS for posting this info.

Hey Apple I shouldn't have to go 3 pages deep to find the answer, this really should be at the top of page 1.

Interesting. I didn't have to go through that hassle it seems some of the prompts where for the "apple" services. All I had to do was open "Music" and login with my appleid. That was enough to sync/fix the issue. Was able to replicate on my MacBook Pro and Mac Pro.

I'm having the same problem. Clicking keychain doesn't work. In fact, it auto unchecks almost immediately after being checked.

On top of it all, I don't really want to use icloud keychain. Apple needs to fix this.

Update for me: After logging out, logging back in, I got the prompt again. This time when I put in the Apple ID password I then got asked to put in the PIN for my iPad. Since doing that it seems to have stabilized.

The keychain is still unchecked in iCloud, which is fine by me.

Not the smoothest upgrade process I've ever seen.

Same problem and same solution here: password changed and all works fine.

My iCloud password was 2 years old and Catalina asked me to review the security of my iCloud account (or something similar, I use macOS in Spanish), so I did it.

Just go to: System settings / Apple ID / password and security / Change password

Don't forget to update the password in your iPhone/iPad/watch....

Like Miguelangelh, i changed my password, BUT the first time, I did NOT log out of all devices--that didn't work.

After changing my apple ID password, I had to LOG OUT of all other devices.

Once I did that, the activation of iCloud keychain was successful, and there were no more problems with my apple ID.

(I also logged back in to Music and the app store before changing my password, which did not work.)

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)

Everyone kept posting what worked for them...and it would work temporarily for me but the problem would come back

here is what worked:

go to iPhone

go to Apple site that lets you change your Apple ID password

change it

sign out on your phone

sign back in...you will have to do authenticification to sign back in...

sign out on Mac...

sign in with the new PW....

again lots of authentification using your phone to sign in on the Mac

that worked...whatever in the process was corrupt it not communicating was reset...

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

Unfortunately that wasn't my problem, as I didn't set up Catalina from scratch, but installed it over a working Mojave. However, as I was about to try your suggestion of another user id, I figured, what they heck, I'll try signing out and back in, and it worked like its supposed to..

I tried everything suggested.... checking the keychain and logging out and logging back in and everything, even updating the Supplemental update and it still prompts for passwords EVERYDAY!!!

This is a serious problem. I think Apple needs to get down to see what went wrong because when you have added so many layers of "security", you actually create more problems.

I may have to format my Mac HD and reinstall the MacOS again which is gonna take a lot of my time.

Checking Keychain does not help. It just endlessly says setting up. In fact this time around it said my passwords were not valid and I needed to be redirected to the change password page. Even attempting to change the password failed and sent me back to this same loop. I have entered my Apple ID and MacBook password multiple times while the Update ID Security prompt remains.