iCloud Keychain not working on OSX Catalina 10.15.7 but fully functional on iOS

Thanks TYGB,

In my case none of the pop ups after the option to keep a copy of the Contacts on the Mac appear - the box simply goes away and I remain signed in.

I have managed to confirm my Apple ID password by deleting all of the Keychain entries that appeared after the restore (their were a HEAP of iMessage ones and a few that were for my Apple ID (which I think were my attempts to confirm the password).

Once I did this and restarted, I was able to use two-factor authentication from another signed in device to confirm the password.

I'll see how long it lasts!

For Mac OS catalina 10.15.7

Open system preferences , click on Apple ID icon .

Click on overview in the side bar and click on sign out .

Click on keep a copy .

In the next upcoming pop up , click on keep on this Mac .

Enter the Apple ID and password and click on continue .

The Apple ID is completely removed .

And again you open system preferences > iCloud the Apple ID icon doesn’t not exist , click on sign in .

It will prompt to enter Apple ID , click on next and password , again click on next , a red notification will appear over the system preferences , and the icon starts bouncing .

Enter the admin password and click on ok .

It will prompt to enter Apple ID , click on next and password , again click on next , a red notification will appear over the system preferences , and the icon starts bouncing .

Again enter the admin password and click on ok .

A small circle will be rotating in front of Apple ID field .

It will prompt to merge contacts , calendars …click on merge .

Click on allow .

In front of iCloud Drive - options check the box of desktops and documents a small circle will rotate , setting up and finally the box will get checked .

The box of keychain is unchecked , tap the box it will be semi greyed for a short while but get checked completely in few moments .

Did you cleaned the hard drive and reinstalled Mac OS or did an archive installation , what is the status of keychain in system preferences , is the box checked , see this article https://support.apple.com/en-in/guide/safari/ibrw1103/mac

Important: Safari autofills your information for anyone who uses your Mac with your user login. It also autofills your information for anyone who uses your other devices, if those devices and your Mac have iCloud Keychain set up.---see this article https://support.apple.com/en-in/HT204085

https://support.apple.com/en-in/HT203783

TYGB - I've got the exact same issue as the OP.

Unfortunately your solutions didn't work for me because:

For Mac OS catalina 10.15.7

Open system preferences , click on Apple ID icon . Done

Click on overview in the side bar and click on sign out . Done

Click on keep a copy . Done

In the next upcoming pop up , click on keep on this Mac . Done

Enter the Apple ID and password and click on continue . No option to enter the Apple ID and password. Once you select to progress after keeping a copy on the Mac, the box disappears and nothing takes it's place. You're not signed out, it just doesn't change.

The Apple ID is completely removed . Nope - still there, still signed in.

And again you open system preferences > iCloud the Apple ID icon doesn’t not exist , click on sign in . Still there - see above

It will prompt to enter Apple ID , click on next and password , again click on next , a red notification will appear over the system preferences , and the icon starts bouncing .

Bizarre issue that has only popped up with the 10.15.7 update. Have restored to a couple of earlier time points, but have the same issue.

See the exact screen shots .

in the above enter same Apple ID the password field then appear , enter Apple ID password you used in Mac it could be eample1@gmail.com or example2@icloud.com to be very clear the account used here is two factor authentication , are you still using secondary authentication account in which three answers for security questions , date of birth , rescue mail address and its password are used , if so clarify .