iCloud Keychain Won’t Sync

[MeLlamanHokage]

Hello all,

Been having some trouble with my cMP and am looking for some guidance.

I have one of these:

I also have:
iPhone SE (1st Gen) on iOS 14.2
iPad (6th Gen) on iPadOS 14.2

My issues are:
1) iCloud Keychain won’t sync my passwords between my macOS and my iOS devices.

Calendar, Notes, Reminders, Drive and the like all sync correctly within seconds but iCloud Keychain won't sync.​

I'm trying to set my phone to be the master of the keychain set and have the iPad and Mac follow.​

The iPhone and the iPad get along just fine but the macOS keychain won't sync with the iOS keychain.​

​

2) Any changes to System Preferences reset after reboot

This includes, but is not limited to, the login items which won't stay removed.​

​

3) The App store returns a "could not complete purchase" error everytime I try to download anything from it

This was fixed by following a post below, but the fix didn't last after a reboot.​

I've tried everything outlined in these posts:
Login Items
App Store Purchases (Temporary fix that reset after a reboot)
Keychain
Keychain again
Keychain yet again
Keychain yet again, again
Another Keychain Post

I called Apple Support and they had me test a new account.
We found that Keychain Sync & Login Items work swimmingly, so I know it's not system-wide.
They also had me try deleting my login items where I discovered that they could not in fact be removed permanently.

I most recently tried reinstalling macOS (without wiping my 10 years of files) and that didn't fix the issue either.

Can anyone help?
Please let me know if you need more information.

Thanks

 

[brianmowrey]

The new account was a new User on the Mac or a new iCloud account?

If the former, why not just use the new User and bin the one that is broken

 

[MeLlamanHokage]

Thanks for the reply!

It was indeed a new user
The reason I haven't tried that is because I'm unsure of how to move my data between user accounts

E: Yeah it looks like I'd have to do each file (1.9TB over 10 years) manually which sounds like a nightmare

 

[brianmowrey]

E: Yeah it looks like I'd have to do each file (1.9TB over 10 years) manually which sounds like a nightmare

Yeah, if you're not already sharing all your files with the cloud, transfer to new User can get messy wrt permissions. My personal approach would be to (after backing up first) move everything except Library in your Home Folder into Dropbox Pro, let it download to the new User, cancel DB pro, and move on in the new User. I am pessimistic about how much effort discovering and
repairing whatever tiny obscure preference file entry is broken in your current User would require.

 

[MeLlamanHokage]

And you don't think I'll have any issues with perms by transferring through DB Pro?

 

[brianmowrey]

And you don't think I'll have any issues with perms by transferring through DB Pro?

Right, as far as my own experience. DB integration with Finder, wherein all User permissions or locks are automatically voided for files in the Dropbox folder even though they still display as User-specific in Get Info, is very sturdy. Whereas Finder's built-in permission-editing via Get Info is basically nonfunctional.

 

[MeLlamanHokage]

Whereas Finder's built-in permission-editing via Get Info is basically nonfunctional.

So this then is the caveat. Finder Get info becomes unusable.
Also I should be able to transfer software licenses and the like correct?

 

[MeLlamanHokage]

@brianmowrey
So I'm trying the dropbox switch now but I've come across an issue where DropBox can't move one of the sub files so it fails to move anything.

E: Nvm. I'm dumb. I didn't realize that the Dropbox folder was inside my home folder. I was trying to move that into Dropbox as well.

 

[MeLlamanHokage]

@brianmowrey
Hey thanks for your help on this
I am still having an issue copying my library folder to a separate location in Dropbox

I remember you saying not to copy it but I need to find a way to preserve it for all these license files for old software that I still use

I have two 2TB hardrives and one is completely empty
The other has 1.9TB full

Problem I'm running into is when I copy my /user/Library over to the dropbox folder separated from the rest of the home folder files, I get an error saying that the transfer couldn't be completed because some file already existed.

But that would be impossible because I'm making a copy in a new location

Any ideas for a work around?

 

[brianmowrey]

@brianmowrey
Hey thanks for your help on this
I am still having an issue copying my library folder to a separate location in Dropbox

Sorry I've been away.

No, I've never experimented with transferring library files at all. After simultaneously losing my main drive and backup to permissions issues, I treat my library in general as a tumor-in-waiting that I need to discard once or twice a year, and only put inportant files in Dropbox. Because I haven't used any apps that aren't linked to App Store or Steam, I have no helpful experience for transferring licenses. I'm sure someone else in the forum has, but it might be more effective to create a new post to the question since no one has chimed in here...

 

[MeLlamanHokage]

Hey so I tried the transfer and now my iTunes Library.itl is locked and iTunes won't open
Also audio files don't work in Finder's Quick Preview