Update AppleID Settings - macOS Catalina

Update: I finally got past this on both devices. It required changing password from the appleid website, restarting my iPhone so I got the same notification in settings there, logging in with new password on iPhone, going back to both Mac's individualy, following the Apple ID and device password prompts as before and now finally got a prompt for the lock pin for my iPhone finally satisfying the update Apple ID settings dilemma.

Surely this would have come up in testing since I was affected 100% on multiple current model Macs

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.

None of the suggestions have worked for me, I've entered the iCloud and computer password more than 20 times, now iMessage stopped working, when I enter the iCloud password to login into iMessage I get "An error occurred during authentication", this is a mess Apple, fix it!!

I changed the password to my account (and dealt with the huge hassle that causes across 10+ devices), then logged the MacBook with issues out and back in to iCloud (and dealt with the huge hassle THAT causes) and was finally able to enable keychain. That machine is no longer showing the error.

However, I can’t enable keychain on any other devices - my ipads, iPhones, and other MacBooks just toggle the switch back off instantly.

And the MacBook is now having a whole host of other issues unrelated to this thread. DnD mode is perpetually stuck on “Presentation Mode” for no obvious reason. USB devices aren’t detected. The dock keeps going away for no reason and not coming back.

I've tried resetting my Apple ID password and signing out on all devices and now I get "Verification Failed: ... error connecting to the Apple ID" server across all my devices when I try to log back in.

This is making the iOS13 upgrade look acceptable.

Hey folks,

Just got off of the phone with Apple support. The tech told me to not reset the password; but, to log off out iCloud on the Mac......and re login.

This worked for me, including fixing the Keychain issue. However, it did force me to re-sync iCloud data. This includes my 26K+ photo library. It’s uploading now over a 1GB connection. I don’t think it’s actually reuploading.....but more resyncing. The tech assured me that there will be no duplicates.

Still having problems updating Xcode.....but that’s it.

Yeah, that’s what my macs are doing now as well. An immense photo library upload. That’s why I always try to avoid logging out of iCloud if at all possible. This has been a rare misstep of an upgrade. Very not-Apple.

I had the AppleID / Keychain issue on my 13" MacBook Pro Touch Bar and tried at least 20-times to enter my credentials. Finally, I opened Safari and logged into iCloud.com website from Safari. Once I did that, then the computer prompted me to Touch ID to authenticate to the iCloud website. Then FINALLY after that it prompted me for my iPhone password. I had to enter the iPhone password twice, then it finally worked. This 13" MacBook Pro appears to be good to go. Your milage may vary, but it worked for me.

Sorry to hear that. One other thing that I did, but did not attribute to helping was rebooted iPhone and iPads. Not sure now, if any of that mattered, or if I just got lucky. I suspect that Apple will figure it out. I would try again tomorrow.

Good Luck,

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.

This is happening to me on my MBP as well. This also happened when I updated my 11" iPad Pro to iOS13. I ended up having to wipe out all of my preferences and restart to get the iPad going again. This is very frustrating. I'm holding off on updating my Mac mini for now.

You can Sign Out in the Apple ID panel and eventually after several housekeeping questions (Find my Mac, etc) you'll be prompted to sign in, so, you Sign in. During the sign in process the system will ask you for the Apple ID, Apple ID password, Mac password, and your iPhone unlock code (if you set up you phone to unlock your Mac, I guess -- not sure why). Worked for me. (The Keychain "fix" didn't)

Signing out of iCloud and back in corrected the issue for me. The turning on iCloud keychain sync did nothing for me. The log out and log in was a little time consuming in both directions, and I'm not a heavy iCloud user, but it did fix my issue. Don't freak out while it's resyncing, though. My MBP fan ran on high for a few minutes and as data streamed back in, contact names in Messages and elsewhere reappeared in batches.

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