Definitely experienced this problem myself. I couldn't sign back in and had multiple authentication failures wit the right password, but it fixed itself after I left it alone and tried later. Same with the Music service, an TV+
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Be careful signing out of iCloud on 10.15.1
- Thread starter BF1M
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Just bought a new MacBookAir that is on Mojave 10.14.6 - Dont dare Update yet ( this one has iTunes)
i think i had the same problem or some kind of related problem.
i wasn't aware of this iCloud sign out/sign in problem before.
but i had to get an update to an iOS (not macOS) banking business app that was only offered in the Hong Kong app store (my main, usual apple ID is associated with a different app store than Hong Kong).
so i signed out of my apple iCloud account on my iOS device - thinking that the only real headache that i would encounter was to need to download all my apple Music songs to my device again (i want them on my device, not just playlist types of links accessible only when you are connected).
i updated my iOS app ok.
signed out (i thought) of that iCloud account, and then signed in (i thought) to my normally used iCloud account.
but then i noticed something very strange:
Messages preference panel said that i couldn't get Messages unless i signed in with the correct apple iCloud account. i actually cant remember if it used the word "correct" but it was something like that.
but i had already been receiving and sending Messages with what i thought was my regular iCloud account.
all my Message history was there. i was getting Messages from people who were using it... really bizarre.
anyway, i signed out of Messages on iOS and signed in using my regular account and iOS Messages hasn't acted funny since that.
but all that was iOS weirdness. now macOS iCloud related:
while all the above was iOS related, when i looked to see if my macOS Catalina Messages, and my iCloud Drive account in my macOS Catalina mac was impacted in any way by the strangeness of the iOS iCloud account, sure enough on my mac i was being repeatedly asked to sign in to different parts of iCloud related services on my mac although it was showing the regular iCloud account info in the main iCloud preference pane.
among them i noticed that Keychain (!) could not be fully selected in macOS iCloud services (not being able to be "fully selected" means that when i selected it, it didn't turn green indicating it was selected. there was light shade of grey check mark instead and it wouldn't turn green to show really selected. eventually this turned to green too later)
but the biggest headache turned out to be my iCloud Drive account (which isnt set to be "optimized" so i have always have 100% of all data on my mac all the time anyway) shifted the location of its iCloud Drive files to a non-iCloud Drive accessible local folder inside Macintosh/Users/Home Folder/ and the folder became labeled as "iCloud Drive (Archive). this folder contained all my data.
and then it began to download all the 68GB of iCloud Drive data that i have on apple's servers onto the normally iCloud accessible area ( and started to slowly populate back the Documents and Desktop folders that are a part of iCloud Drive.
the only interesting (meaning good) part of this was that i was happy to see that iCloud Drive didn't just delete the files on my mac (over the years i had read that if you decide to cancel iCloud Drive it will delete all the files on yr mac and you have some weeks to download them again to yr mac. but it didn't do that - it shifted them in-tact to a totally local place only. maybe this is due to the fact that i have never chosen to optimize iCloud Drive).
i have decided that after the next .point update to Catalina that i will just backup everything a couple of different ways, and then wipe the disk totally and start with nothing on it other than Catalina and then reimport my data. my thinking is that probably this iCloud profile issue corrupted people's data structure in an infinite variety of ways, and apple cant put it all back together.
so i will just wipe it and start fresh with the next .point release.
when people ask if they should update to Catalina, it doesnt get a lot of mention. but the way that Catalina and iOS 13 have been very tightly integrated, coupled with highly sensitive iCloud authentication techniques means there will be these problems. but i like the direction apple is headed to with this very integrated approach. but needing to understand the way it all works (or, is supposed to work) is becoming difficult...
i wasn't aware of this iCloud sign out/sign in problem before.
but i had to get an update to an iOS (not macOS) banking business app that was only offered in the Hong Kong app store (my main, usual apple ID is associated with a different app store than Hong Kong).
so i signed out of my apple iCloud account on my iOS device - thinking that the only real headache that i would encounter was to need to download all my apple Music songs to my device again (i want them on my device, not just playlist types of links accessible only when you are connected).
i updated my iOS app ok.
signed out (i thought) of that iCloud account, and then signed in (i thought) to my normally used iCloud account.
but then i noticed something very strange:
Messages preference panel said that i couldn't get Messages unless i signed in with the correct apple iCloud account. i actually cant remember if it used the word "correct" but it was something like that.
but i had already been receiving and sending Messages with what i thought was my regular iCloud account.
all my Message history was there. i was getting Messages from people who were using it... really bizarre.
anyway, i signed out of Messages on iOS and signed in using my regular account and iOS Messages hasn't acted funny since that.
but all that was iOS weirdness. now macOS iCloud related:
while all the above was iOS related, when i looked to see if my macOS Catalina Messages, and my iCloud Drive account in my macOS Catalina mac was impacted in any way by the strangeness of the iOS iCloud account, sure enough on my mac i was being repeatedly asked to sign in to different parts of iCloud related services on my mac although it was showing the regular iCloud account info in the main iCloud preference pane.
among them i noticed that Keychain (!) could not be fully selected in macOS iCloud services (not being able to be "fully selected" means that when i selected it, it didn't turn green indicating it was selected. there was light shade of grey check mark instead and it wouldn't turn green to show really selected. eventually this turned to green too later)
but the biggest headache turned out to be my iCloud Drive account (which isnt set to be "optimized" so i have always have 100% of all data on my mac all the time anyway) shifted the location of its iCloud Drive files to a non-iCloud Drive accessible local folder inside Macintosh/Users/Home Folder/ and the folder became labeled as "iCloud Drive (Archive). this folder contained all my data.
and then it began to download all the 68GB of iCloud Drive data that i have on apple's servers onto the normally iCloud accessible area ( and started to slowly populate back the Documents and Desktop folders that are a part of iCloud Drive.
the only interesting (meaning good) part of this was that i was happy to see that iCloud Drive didn't just delete the files on my mac (over the years i had read that if you decide to cancel iCloud Drive it will delete all the files on yr mac and you have some weeks to download them again to yr mac. but it didn't do that - it shifted them in-tact to a totally local place only. maybe this is due to the fact that i have never chosen to optimize iCloud Drive).
i have decided that after the next .point update to Catalina that i will just backup everything a couple of different ways, and then wipe the disk totally and start with nothing on it other than Catalina and then reimport my data. my thinking is that probably this iCloud profile issue corrupted people's data structure in an infinite variety of ways, and apple cant put it all back together.
so i will just wipe it and start fresh with the next .point release.
when people ask if they should update to Catalina, it doesnt get a lot of mention. but the way that Catalina and iOS 13 have been very tightly integrated, coupled with highly sensitive iCloud authentication techniques means there will be these problems. but i like the direction apple is headed to with this very integrated approach. but needing to understand the way it all works (or, is supposed to work) is becoming difficult...
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