iMac, iCloud Keychain checkbox won't sync

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iMac, iCloud Keychain checkbox won't sync

Older iMac (late 2013) I recently upgraded to max allowable macOS, Catalina 10.15.7. Upgrade went reasonably well from Sierra --> High Sierra --> 64 bit upgrade on all apps --> Catalina. All was fine for about a week, then went into system preferences, iCloud --> and noticed Keychain was not checked (when it had been checked on setup). The Keychain Access app was populated on the system at some point.

When trying to activate Keychain sync with iCloud checkmark on the iMac, I got various boxes about needing end-to-end encryption updates. In that process I got boxes asking for login-admin ID's for my other Apple devices, i.e., MacBook Pro, iPhone. It was a very slow process taking 5-10 minutes between the ask boxes. Then, It started to loop the same ask boxes one or two cycles, eventually ending up with iCloud Keychain unchecked. Now I'm getting a red dot on System Preference dock icon after start up saying... Update Apple ID Settings (caution triangle). When trying I get caught in the same loop.

I Went though 2 days of suggestions here and other websites, nothing worked. Hesitant to go into Keychain Access app --> preferences --> "Reset My Default Keychains" for fear of using 10-15 years of password data.

For the first time in a decade I called Apple Support. At their suggestion over 2 days, Disk First Aid, Safe Boot, Catalina clean reinstall. They finally gave up and suggested Genius Bar, or re-install High Sierra.

The online consensus seems to be a corrupted Keychain iCloud verification file, but there's no solution for fixing it. Any help would be appreciated

iMac 27″

Posted on Aug 11, 2023 5:59 PM

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Answer 1

Top-ranking reply

applegurl79

Level 1

14 points

Jun 26, 2024 5:25 PM in response to ysquared

I am working on a solution :)

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Answer 2

ysquared Author

Level 1

10 points

Aug 12, 2023 12:42 PM in response to tygb

Thank you tygb. I did see your (this recopied) post on this topic from a few years back. Some of the suggested solutions seem a bit drastic, i.e., changing all of my Apple ID info. I'll save that for a last ditch effort. There should be a much easier solution to this.

Also, I'm not getting similar notices as your screenshots. I'm not being asked to "Upgrade My Account Security." I've had two factor authorization enabled for years (and it can't be turned off). My online Apple ID account confirms it. After restarting several times, each time I'm still getting the dreaded red dot in the dock on System Prefs. When I go to Apple ID, "Update Apple ID Settings," -->> continue, sign in again, then I'm still getting caught in a loop of boxes asking for the login passwords for my other devices. Taking 10-20 minutes in between each box. You'd think instead of asking for passwords to confirm, it'd send a verification code to those devices, then inserted back on the device I'm using. That's what I thought 2FA was supposed to do. That's not happening here. After hours, I still end up no iCloud Keychain, check-boxed.

In continuing to solve this I've tried other online suggestions, i.e., Keychain app --> Preferences --> Reset my Default Keychains. No joy. I removed the Keychain folder from the User Library, restarted, again trying enable iCloud Keychain checkbox, No joy.

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Answer 3

ysquared Author

Level 1

10 points

Jun 27, 2024 11:08 AM in response to applegurl79

Thank you applegurl79. I received your email with the proposed solution to this still ongoing problem. When I went into Keychain (Step 3), looking for your suggestion "address/Apple ID" file (Step 4).... the closest file I can find to your description is the "appleid.apple.com (myemailaddress.net)". It's found in the Keychains + All Items (left panel choices) and searching "appleid"

When opening that file with "Attributes" tab that's highlighted it's fill-in panels - Kind: Web form password, Account: populated with my Apple ID Account name (email address), Where: web address https://appleid.apple.com, Show password: works and is correct for my ID account.

When opening the "Access Control" tab within the file I get "Access to this item cannot be edited." with "Access group for this item" named "com.apple.cfnetwork", which I cannot click on.

Please advise if I had the correct KeyChain file you suggested. Thank you, but at this point it's still no joy.

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Answer 4

tygb

Level 9

64,748 points

Aug 12, 2023 6:21 AM in response to ysquared

In Mac OS catalina if an error shows some account services will not be available until you sign in again ( update Apple ID settings ) .

Open system preferences , click on Apple ID icon and again click on iCloud in the side bar , it prompts to enter the Apple ID and password ( enter the password ) , after that a pop up window appears to upgrade with 2FA , click on continue , the circle in front of keychain box started rotating setting up , after a while it prompted to enter the admin password and finally the box of keychain will get checked the small circle rotating in front of keychain setting up will disappear ,

You have to convert secondary authentication account to 2FA , the error will go away .

If the trusted number is not yet added verify it , click on name , password , email in the side bar , click on edit see these articles .

Change your Apple ID information

Change Internet Accounts preferences on Mac - Apple Supportsupport.apple.com › en-in › guide › mac-help › Mac

Change Overview preferences for your Apple ID on Mac ...support.apple.com › en-in › guide › mac-help › Mac

Change Password & Security preferences for your Apple ID on Mac

Change Payment & Shipping preferences for your Apple ID on Mac

Change Media & Purchases preferences for your Apple ID on ...support.apple.com › en-in › guide › mac-help

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Answer 5

tygb

Level 9

64,748 points

Aug 12, 2023 8:04 PM in response to ysquared

When 2FA account is permanent , the secondary authentication account is automatically disabled , the function of iCloud keychain box exists in secondary authentication account only , the box for iCloud Keychain is checked or unchecked or can't be checked has no importance in the 2FA account .

The 2FA account is created from hard ware address of a primary device , it send codes to the trusted device .

Note : you don't need to reset default keychain from keychain access , this will delete login keychain password as well delete passwords saved in iCloud Keychain , and new empty login keychain will create in user library > keychains folder .

Also various pop - ups will start appearing on the desktop , for Apple ID , your third party mail services accounts like gmail , and login passwords .

And don't delete keychains folder from user library , this is done in a very rare scenario when keychain is corrupted .

Also , the other devices lile a Mac should not be signed in with same admin name / password of your primary Mac .

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iMac, iCloud Keychain checkbox won't sync

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