iCloud Authentication Problem

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Level 1

4 points

iCloud Authentication Problem

I recently changed the password on my AppleID. When I did so, I logged out all my other Apple devices (6 of them). When I logged back into my devices, none of them were able to authenticate with certain iCloud services (iCloud Keychain, Advanced Data Protection, etc).

The loop proceeds as follows:

System Settings gives a notification that I need to update my AppleID settings. As you can see, I am logged into my AppleID, so we can accept that I know the correct password for the account, and that is not the problem.

Clicking "Continue" brings up the following prompt:

I enter the password, which leads to the next prompt:

Fair enough and pretty self explanatory. The example photo is from my primary laptop, and the same prompt comes up on all my devices. The prompt appears slightly different on iOS devices, but is fundamentally the same.

I enter the device passcode and the following message appears:

Clicking continue takes us back to the first image in an endless loop. Clicking cancel has exactly the same perceived effect.

Now, if I go to the iCloud panel:

And I attempt to turn on "Passwords and Keychain" I get the following:

I toggle the slider, which prompts:

Pressing "Continue" brings up:

If I am on an iOS device, the prompts look slightly different, but are functionally the same.

I enter the password, which causes the device to pause for a log time while it tries to communicate with the server. Then this window pops up:

Clicking "Continue" or "Cancel" takes us back here, ad nauseam (with the slider in the OFF position):

The same loop happens when trying to turn on Advanced Data Protection.

Lastly, I can't get Access iCloud Data on the Web to turn on, either, so there's no way of managing this directly on Apple's servers, either. This appears to be a timeout issue. Attempting to turn this on results in a long delay, then I get this:

I have tried logging out all my devices and logging back in. I have tried a complete wipe and reinstall of my iPhone (all that did was completely delete my keychain on the phone THANKS!). I have tried removing all devices from my Apple account, except my laptop. I have changed the AppleID password three times. Nothing has had any positive effect.

Changing networks has no effect. Taking iPhone off wifi and forcing mobile data does not work, not does the reverse. My network is not firewalled, and I am the admin of my local network. All other services are working flawlessly. I am not on a VPN. My connection to the ISP is not double NATed.

I have exhausted all the available advice on this message board, and Google at large.

Any other thoughts or ideas?

MacBook Pro 16″, macOS 13.4

Posted on Jul 1, 2023 8:54 AM

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Answer 1

Drew_7

Community Specialist

Jul 3, 2023 10:51 AM in response to SHGillette

Hello SHGillette,

Based on the issue you've described and the extensive steps you've already taken it will be necessary to reach out directly to Apple for continued support. You can review options available in your region here: Get Support

Best regards!

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Answer 2

SHGillette Author

Level 1

4 points

Aug 25, 2023 9:25 AM in response to SHGillette

This is a follow up on my original post.

As Drew_7 noted, this is an issue to be resolved by an Apple Support Specialist. I opened a support ticket with Apple and got an immediate response, via online chat. The specialist went through the issue several times with me to confirm the problem. The problem was beyond the skills of the online support specialist, and I was referred to the next level of support, which happened over the phone. The phone support specialist very helpfully and thoroughly confirmed the problem over a very long phone call and documented everything. At the conclusion of the phone call, the specialist needed to confer with Apple engineering about the problem, but scheduled a follow up call for the next day.

We had an equally long and respectful telephone troubleshooting session the next day, which also did not resolve the problem. The support specialist advised me that he would call again the next day with further troubleshooting attempts, but cautioned me that we were unlikely to solve the problem, and that the problem would likely have to be corrected by a software update in the future.

The next day the phone rang. I answered, and was immediately disconnected. I got an email from Apple acknowledging the disconnect, and a link to try to re-establish contact, which I followed. Apple has entirely ghosted me since then, despite numerous attempts to follow up.

What we were able to clearly establish in the troubleshooting sessions is that the issue persists on ALL of my Apple devices, running several different operating systems- two different versions of the desktop OS on three machines, two versions of iOS on two iOS devices, and also AppleTV OS on an up-to-date TV4K. As such, it would appear that the problem is not with my devices, but rather a server side issue.

In the meantime, there are other Apple services that do not work because of this issue-

My AirTags are all bricked because I can't establish an end-to-end iCloud connection.

My AppleCard is mostly useless, as it also depends on end-to-end encryption in order to put it in Wallet.

While I've been tempted to establish a fresh AppleID, I think this would create more trouble than it fixes, as the AppleCard is linked to the AppleID with the problem and I haven't found any means of moving it to a new AppleID.

While I'm hopeful that the new operating systems coming out may fix this, I'm doubtful, as it's clearly a server issue. What concerns me is that I've been ghosted by Apple for close to two months, and starting to suspect that the problem for a small group of users affected isn't worth the engineering time to troubleshoot and solve.

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iCloud Authentication Problem

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