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Catalina keeps asking me sign into iCloud  

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I don't know if anyone here can help with this annoying problem.  Seems like every other day in System Settings in Catalina under iCloud it will tell me I need to sign into iCloud to update settings before iCloud will work again.  So I enter my iCloud password, then it asks for my Mac login password, then my iPhone password.  But it keeps asking this every couple days.  

What happens also if I look at my iCloud settings before entering my passwords, keychain is unchecked where it usually should be.  So it keeps unchecking keychain in my iCloud settings for what I sync.  I tried searching the apple support pages but nothing helped.  I signed out of all my iCloud accounts on every device I have and signed back in but the problem remained.  I hoped it would be fixed in the recent update to Catalina but every problem I'm having with this mess of a OS remains.  

It doesn't ask me to sign in again on my other devices like iPad, iPhone and Apple TV.  Just my Mac which is a 2014 Mac mini running the current most up to date version of Catalina.  I would just do a fresh install but I upgraded to Catalina from the previous OS.  How iTunes is now with spreading stuff all over the place I fear doing a fresh install.  It was easier before just to copy the iTunes folder.  I keep hoping apple will fix this but not sure if anyone else has been struggling with this as well.  

1 Answer
1

I would suggest sign out of your iCloud (Mac) and then restart your device. And then sign in with your Apple ID and password.

@jigneshpadhiyar

I already said in my post I did that and it didn't help.

@jigneshpadhiyar

One thought: did you sign out, reboot, and then sign back in? I know that seems subtle, but I've seen that reboot-while-signed-out solve some things.

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