Keychain won't work in Catalina

I got it to work after changing my apple id password. It then asked both for the login password and for the passcode for my iPhone, which seemed to complete the authentication to its satisfaction.

I have a second Mac still on Mojave, and it does not require the additional steps to authenticate for iCloud keychain use.

I encountered a problem where it appears that more requirements were imposed on the iCloud password and the messages when passwords that don't meet the requirements were unclear. Make sure the password contains both upper and lower case letters and at least one numeric digit. There are also some situations such as "password", "secret", or the Apple ID as the password will cause problems. I'm not sure what the minimum length of a password is, but it appears to be eight or nine characters. It may also be necessary to set up security questions. https://support.apple.com/en-us/HT201487 and https://support.apple.com/en-us/HT201303 may be useful.

I'm having the same issue, but it is affecting not just my Mac but also my iOS devices. This has disabled my use of Apple Pay and HomeKit (Home app) as well.

I've been through the usual password change but no luck so far. Spent almost 3 hours with Apple support and they said it is a software issue on the server side but no idea as to when it will be fixed.

Exact same issue -- not fixable.

I have to deal with a nasty notification showing on my iPhone's home screen saying to update my apple security settings and the same notification on my iMac running Catalina. I click to try and update and put in my password and nothing happens both on my iMac and phone.

I logged out, checked all my ID settings, changed iCloud password, even removed my fingerprint and passcode on my phone -- NOTHING WORKED. But get a load of this -- I can't set up fingerprint as a passcode anymore on IOS because it hangs now as well.

THIS ALL STARTED WHEN I ENABLE TWO FACTOR AUTHENTICATION on Catalina. Before that no problem, but of course now -- I don't have an option to turn it off anymore, which might fix things.

In all my years as a Mac owner I've never had issues like this before. Very frustrating!!!!

Same problems here; I always wait a bit with updating my devices, so I ran the update last week. Tried to install HomePod. Didn't work. I had to turn on keychain (but it was already turned on). So I slide it off, I want to slide it back on, and BAM nothing anymore. Now I got this funny problem: "To enable iCloud Keychain, review and upgrade your Apple ID security." I can not even use my Home app anymore! I need to turn on keychain :(

Just called Apple helpdesk, the guy tried to be very helpful, but couldn't fix it. He found information that the issue is known with Apple, and that they are working on in it. Keep an eye on the upcoming updates. That's thé Apple Solution now? I am getting frustrated with Apple lately. More and more issues, even BIG issues...

I've changed the password too and am still having the same issue. Everything works fine on our iphones & ipads, it's just the Mac that is having this problem ever since updating to Catalina. Very frustrating! :(

Im also having this issue since upgrading to Catalina. Non of my other devices are effected at all including a second Mac on Mojave!

Apple needs to correct this ASAP before we all move to another password software solution!

I also have this problem, have had 3 hour long calls with apple support where they have made me create a new login, change my password, restart in safe mode, and of course turning off and on again multiple times. I also have a constant notification in settings that says I need to update my settings to use certain features.. However when I click this and enter my password nothing happens. At this point I feel like giving up on using apple as I have put way too much time in trying to resolve this. Really hope this will fix itself at this point.

Still having the very same problem since Catalina. We're on 15.3 already and this issue STILL persists.

I've also changed my password (after a couple of rounds re-doing the validation) and also as directed by Apple Support logged out with my account from ALL devices (MacBook, iPhone, AppleTVs) until the AppleID shows no connected devices anymore.

Still - today (two days after that exercise) I'm back in the same verifcation loop!

But it seems that contrary to others here, after I enter my AppleID PW, MacPW and Iphone Code, the message goes away and also KeyChain is checked (or can be activated). So it all works for me until after 2 or 3 days it's back to the same message. Also I have no problem on iPhone or other devices, just Catalina.

I had 2FA active with my AppleID since years... so it's definitively an macOS Catalina problem.

How on earth is nobody at Apple looking at this and fix it???

This issue occurred after changing password! What is the next step?

I'm having exactly the same issue.

I hope that correction will come real soon !!!

Mac is now very hard to use without it :/