Update AppleID Settings - macOS Catalina

After entering my Apple ID and Mac password several times, it prompts for my iPhone PIN. I've never had to enter my iPhone PIN on any device other than my iPhone so this seemed a little suspicious. Why is my Mac asking for my iPhone PIN? This whole process seems to be poorly implemented.

Michael Keenan's solution did not work. I did as instructed, but the Keychain unselects after about thirty seconds and I am put right back into the cycle.

NOTE: This may have something to do with the fact that I deselected an old device from the list to the left in "Apple ID." For the first time ever, when I did that, a message came up instructing me to change my Apple ID Password. After that, I have received no further prompt to do so, but I assume that is the source of the problem.

I am loathe to change my Apple ID password. I know that there is no security breach. If I do change it, I will then have to do it on my iPhone, Apple TV, etc.

Good grief!

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.

THIS WORKED FOR ME!!

Turned out my iPad backup had been turned off for a few months and I didn't notice that. I just turned backup back on and went back to this issue on my Macbook, tried signing in again for the 10th time in Settings > AppleID and this time it asked me for the passcode I use to get into that iPad. Plugged that in and BAM, fixed the issue and my Macbook is good to go now. I wonder if turning that on and off on other devices would work for others, worth a try.

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

Certainly would have helpful, as part of the update process, to include instructions on how the iCloud sign-in and other security measures were impacted (including use of the iPhone code). Might not change the effort required but would at least help with understanding.

Badclamz, glad to see you resolved it.

I tried exactly what you did about forty-five minutes ago. Now, I can’t log back into my Apple account on my Mac. The status wheel just keeps spinning.

oh, well.

One of the issues you may have is an incomplete log-out. This happened to me on Sierra when I upgraded and tried to resolve some account services not starting while other iCloud services seemed okay. What seemed to have happened in that case was that even though I chose "Sign Out" from iCloud, it attempted to sign me out but didn't sign me out (and I'm not sure if it was because I had enabled "unlock my Mac using my Apple Watch" but that was my suspicion at the time. What happens when you completely reboot the Mac and try to enter your Apple ID credentials there?

I have the same issue and I'm even not able to activate the keychain. It asks for icloud login, then it's for a moment activated, then it begins again with the icloud/apple id login loop. At the end keychain is still inactive. Tried it 5 times. No success. Any ideas?

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.

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)!

I had a bit of a struggle with this; in my case I was able to resolve it (I hope( by first enabling the keychain in the iCloud preferences,, entering passwords (again), logging out of iCloud, rebooting, and then logging back in. While I was trying to log out of iCloud, I ran into a repeated prompt about Photos updating my library. Telling it to basically go ahead and leave anyway led to a message telling me that I'd lose some low-res previews, for which I carted not. That seemed to break the logjam.

However, I did almost get fooled by the whole "unlock code" .vs. "passcode" issue, as I first ran around the house looking for my phone before I re-read the prompt. Annoying.

Dear Apple: This, plus the SNAFU with the "Terms and Conditions" loop has made this the worst macOS update in a long while. I feel like I'm back in the days of 10.3 or so. It's doubly-difficult when you're visually-impaired, as all those prompts and loops are disturbing.

This FINALLY kinda worked..lol. I had to do so many things though I don't know if I can remember everything..VERY frustrating@! The first time I attempted this, it seemed to work. The Keychain square was ticked. But then after several seconds it went unticked again.. It kept asking me for AppleID password and Mac password many times. It would show Setting Up at the Keychain item, then after entering Mac password, the setting up would go away but the box would stay unchecked. Did this several times! I kept reading through this thread and saw some people reset their AppleID password and that helped, so I did that as well(I had a strong password to start with BTW...) Of course, went thru this at least 2 more times. FINALLY on my MacBook Air it asked for the passcode to unlock my iPhone. I put that in and then it seemed everything worked. VERY frustrating, especially after waiting for hours for it to finish "Setting up Mac" last night.. I let that go all night and it was still there this morning. Power off Restart fixed that... I know security is important, but things are just seeming to be getting too complicated. Great community here though helping each other out with the quirks. Hope Apple fixes these glitches. I was hesitant even attempting this upgrade as I was reading of some of the issues people were having. I didn't have any issues going from High Sierra to Mojave. This one was almost a bit too much... Now, off to solve my 32bit app issues.. Thanks Michael/All.

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.

with Apple Support on the line, I did the exact same thing on my iMac: I created a new user profile and was then able to log on to my Apple Account, use iCloud, etc.

Apple Support recommended that I erase my boot drive and do a new install of Catalina, which I did.

So far, all is well, EXCEPT that the App Store app says I have no purchases, which is decidedly not true. I have not been able to figure out that one yet. I assume I will not be able to use PixelMator Pro, etc., but I have not yet tried.