Update AppleID Settings - macOS Catalina

This worked for me too - AFTER I re-enabled iCloud Keychain from my iPhone (which I never turned off). Once I re-enabled on my iPhone my Mac finally asked me for my iPhone passcode and completed the process.

I imagine Apple will need to address this for the masses

I ended up having to log out of iCloud and back in...the Keychain suggestion Michael Keenan suggested didn't work for me...but Keychain was unchecked and refused to stay checked no matter how many times I clicked it and re-entered my password. So it's clearly related somehow, but I had to logout and log back in.

Yeah, this was a bit frustrating before Googling and landing here, so thanks for everyone's collaboration. The only way I could resolve this was to sign out of iCloud on my MacBook running Catalina, and then sign in again, using my iPhone's passkey. Unfortunately this created the need to back up iCloud data on my MacBook beforehand before proceeding, which I was a bit wary of. Like many others have said, Keychain was not enabled after upgrading and no number of attempts to enable it were successful. Thanks again for pointing me in the right direction

I went through the same process of thinking I got keychain set up and then it went right back to being unchecked. Signed in to Apple ID at least 30 times. Eventually bit the bullet, signed out of iCloud and then back into iCloud. That fixed the problem for me. Now waiting for all of my iCloud stuff to download.

Here's what I did that fixed it.

1. In System Preferences Click on AppleID

1. Go directly to iCloud, do NOT click Continue to upgrade AppleID Settings
2. Scroll down to Keychain and click the check box
3. Wait until it asks for password, enter it.
4. It also asked for the passcode from my iPad Pro, enter it
5. It then displayed and asked for a 6 digit code, enter it.
6. Problem solved, no more prompts.

Weird.

I was in the same boat as most here. Kept entering the password over and over again and no luck. I paused for 3 days hoping that maybe Apple would push an update. So today I decided to try again. Here is what I did and it worked.

My MacBook Pro's password was the same as iCloud password. So after remembering a while back that Apple separated the two and advised to make them different, I changed the password on my MacBook Pro to be something different from iCloud. I then logged out of the macOS, logged back in and went back to iCloud clicked the update. It asked me for iCloud password, I entered that, then asked for Mac password, I entered the newly changed one (different from iCloud now), then it asked me for numeric code I use to unlock my iPhone (this prompt was new this round), and voila! It all worked and no more loop.

If you are in the similar boat as I am I hope this will help you :)

Cheers!

This also worked for me. Login to appleID website - BUT do not allow it to use your system password - instead login as you would with your AppleID password. Then, I got a security prompt on my Mac. Back to settings and toggle the Keychain - receive MFA prompt and enter. Finally worked.

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.

I can tell you what worked for me. Some have suggested signing out. When I went to do so, it told me that some items had not been uploaded to iCloud Drive. With that in mind, rather than singing out I:

• Turned off iCloud Drive. It asked if I wanted to stop sync, I said yes. It put my entire iCloud Drive in the archive folder. I think it thought it was out of sync but it wasn't
• This allowed me to turn on iCloud Keychain
• After doing so, the funky message went away and I turned iCloud Drive back on

I'm kinda thinking iCloud Drive was the culprit. It was trying to sync the entire folder after update (2.5g for me).

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.

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.)

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...

I gave up and called Apple support. They answered in two minutes and were very helpful in getting the problem fixed in a matter of minutes. In essence, you have to sign out of your Apple ID and then sign back in, something one never does on a day to day basis. It fixed the problem for me. However, it is still a bug in the OS and Apple should not miss or ignore this one.

have had same problem with keychain refusing to stay ticked and endless Apple ID password prompts for 2 days... after reading through 12 pages of forum discussion today, this finally worked:

signed out of apple ID

switched off Mac and switched on again (not a restart)

signed in to Apple ID - was prompted for my iPad lock numeric PIN

entered PIN

bingo.... everything worked

not a great upgrade this - 25% of my 1650 music albums have lost the album artwork embedded in the mp3 files (which used to display fine in iTunes)

I moved to Mac because I hated Windows 10... sometimes I wonder.... come on Apple, do better than this!!

I was having the same issue. To resolve it I tried updating my iCloud Keychain by going to system setting, Apple ID, clicking on iCloud and placing a checkmark in the keychain box. After putting in all my passwords (several times) it just stopped and the checkmark had disappeared. So, I turned on Find My Mac and then went back and marked the keychain in iCloud again. After putting in my passwords, everything worked just fine.