Weird iCloud Keychain bug

[zorinlynx]

So get this, iCloud Keychain is mysteriously unchecked in iCloud settings. When I check it, it asks for my Apple ID password and I have to enter my Mac's password. But after some time it unchecks itself again.

Meanwhile, even though it's unchecked, iCloud keychain IS WORKING. It's actually functional and syncing changes to other devices.

Has anyone else seen this? I'm starting to regret updating my laptop to Catalina. This release is truly a mess.

 

[nikster0029]

Happening to me as well. I did not notice that it was still working, which is good. If you log out and log back into to iCloud, did it fix your issue?

 

[zorinlynx]

Happening to me as well. I did not notice that it was still working, which is good. If you log out and log back into to iCloud, did it fix your issue?

I haven't done that because logging out and back into iCloud is an extremely painful experience; it has to resynchronize my iCloud Photo Library which takes literally a day or more.

Since everything is working I'm just going to use my machine and not worry about it; hopefully this bug will be fixed in .1.

-John

 

[revmacian]

I just checked my iCloud Keychain setting on both my iPhone XR and iPad Air 3 and they’re checked - I haven’t done anything with this particular setting, I guess it was automatically enabled several iOS versions ago.

 

[adambadamh]

Having this issue too. Stuck in a never ending loop of it looking like it works only for the alert to come back and it asking me to re-log in.

 

[burgman]

Only thing that fixed it for me was to logout and back in. When I did my two factor authorization worked. When I was going through the asking for Sign loop it never did. All is well now.