Apple Unending Hell: why multiple Macs over 8 years cannot use Apple Mail to Send

[glennf (Glenn Fleishman)]

@ace

@scstr

Of course you now have other problems, as Apple tried to resume sync’ing with iCloud by asking you for devices YOU NO LONGER OWN–if you’ve owned two dozen devices and don’t recall which passcode was for each, then Apple’s security defeats you. I’m fighting this battle now. Maybe I’ll start a new thread.

@glennf probably knows more about this multi-device authentication than anyone. Glenn, what do you do if you don’t have the devices in question anymore?

Yes, there’s a particular issue is that Apple bootstraps certain kinds of end-to-end encryption that only devices have access to—maybe just Keychain? In that scenario, the first device added has its passcode (or macOS account password) hashed and used to encrypt the storage set as synce to iCloud.

On the second device in an iCloud set, you use the passcode/password for the device that was first. This allows decrypting the synced data, and now you have two devices. For subsequent devices, I am trying to recall if you’re always prompted for a previous passcode or if there’s enough data between two devices to let you authenticate from another device?

I believe if you disable iCloud’s Passwords sync on all current devices, you may then be able to re-enable Passwords and only be presented with passcodes sequentially from each device as added.

You might also look at your list of devices in Apple Account and remove any old ones if they’re lingering in the list, such as via account.apple.com > Devices.

[dave6 (Dave Scocca)]

@glennf

On the second device in an iCloud set, you use the passcode/password for the device that was first. This allows decrypting the synced data, and now you have two devices. For subsequent devices, I am trying to recall if you’re always prompted for a previous passcode or if there’s enough data between two devices to let you authenticate from another device?

I ran into a related bit of confusion – I have the same passcode on multiple devices, and when I entered the passcode for the device it had requested it said “no, not the passcode for THIS device, the passcode for the OTHER device”. I assume it first fed the passcode to the device I had in my hand, and when that device responded “yep, that’s the passcode” it decided I was mistaken rather than allowing the possibility I used the same passcode more than once.

[glennf (Glenn Fleishman)]

@dave6

I ran into a related bit of confusion – I have the same passcode on multiple devices, and when I entered the passcode for the device it had requested it said “no, not the passcode for THIS device, the passcode for the OTHER device”. I assume it first fed the passcode to the device I had in my hand, and when that device responded “yep, that’s the passcode” it decided I was mistaken rather than allowing the possibility I used the same passcode more than once.

It should identify which device–you’re sure you entered it correctly the first time?

[dave6 (Dave Scocca)]

@glennf

It should identify which device–you’re sure you entered it correctly the first time?

Phone and iPad have the same passcode. Was on phone, it said “enter passcode for iPad”,and when I did it said “No, not the passcode for phone, the passcode for iPad”.

[scstr (Suman Chakrabarti)]

@dave6

Phone and iPad have the same passcode. Was on phone, it said “enter passcode for iPad”,and when I did it said “No, not the passcode for phone, the passcode for iPad”.

That is truly bizarre, Dave. Don’t do what I told you; just do what I’m telling you!
That’s like an old comedy bit like Who’s on First.

Maybe the chain of bootstrapping devices has a bug involving a loop backwards along the chain? I’ve seen database corruption lead to that kind of mistaken lookup from a record to another record and back to itself. But I’m only guessing, and I defer to Glenn on his much greater experience.

@glennf

[…] In that scenario, the first device added has its passcode (or macOS account password) hashed and used to encrypt the storage set as synce to iCloud.

On the second device in an iCloud set, you use the passcode/password for the device that was first. This allows decrypting the synced data, and now you have two devices. […]

That bootstrap chain is fascinating. I didn’t realize. Of course that’s why I had started reading Glenn’s book, but I hadn’t gotten to that part yet.

I believe if you disable iCloud’s Passwords sync on all current devices, you may then be able to re-enable Passwords and only be presented with passcodes sequentially from each device as added.

Something worth trying after the following advice from @glennf which was directly in his book …

You might also look at your list of devices in Apple Account and remove any old ones if they’re lingering in the list, such as via account.apple.com > Devices.

And that’s why I had started reading Glenn’s book on Apple Accounts.

It had exactly this advice and link there. I’d gone to the indicated link after reading the guidance. There are:

• 6 Apple TVs
• 3 HomePods
• 2 Macs

• – both in current use,
  and both of which had this unending hell with Apple Mail being unable to Send
  I fixed the Mac Studio
  I intend to take the M1 MacBook Air and continue troubleshooting it with other advice from this discussion at a later time

• My current iPhone
• My current Apple Watch
• My current iPad
• and fiiiiiiive goooooolden riiiiiiiings!

None of these devices were offered to me for authentication by Apple. It took me a while to realize that Apple was asking me about devices I no longer had.

1. I try to name my devices uniquely, so I can try to keep track from purchase to purchase
2. But after a long enough time and dozens of devices, I don’t necessarily remember which CPU, which generation of device I was using simply by the name.
3. I don’t think it’s advisable to name a device “3rd generation iPad” for example, because that is the name visible to anyone snooping on that Wifi network
4. Any caveats to that, or am I overthinking it?

This sequence of three screen shots is typical of the many attempts I made after I got the System Settings Dialog that Some iCloud Data isn’t Syncing:

The first dialog from System Settings

At first I didn’t notice it wasn’t asking me about my CURRENT IPAD

Verification Failed

I’m used to authenticating, so I initially didn’t notice it saying that Verification Failed; NOT that my passcode was the wrong passcode

Incorrect Passcode

This is when I realized–after I tried a different passcode. My first passcode had apparently been correct, but verification still failed

And that’s where I ended up.

Still have more to read in Glenn’s book. Still have a few ideas to try.

But the point is that I no longer remember which past iPad was “SUMAN’s iPad”. The name alone isn’t enough. I don’t always use the same passcode.

The same thing happened to my iPhone. I started with the iPhone 3G and have owned at least 5 since. I can locate that screen shot if need be, but the point is that I don’t remember that name, and by itself I don’t remember which passcode it would be.

Edit: I located a couple of screenshots, but the name “iPhone” is meaningless to me…

To be continued …

P.S.

Of course I have appreciated all responses thus far. Having been repeatedly humbled, I’m certainly not too proud to admit my flaws

[mpainesyd (Michael Paine)]

So maybe the latest logic in the Apple process is… first check if the entered passcode is the same as the current device, if yes, display warning message and wait for a different passcode for another registered device… endless loop!

[paal (P. Boersting)]

My advice, simply based on me being in this situation several times: Click on “Don’t know passcode?“ until you get a device you are sure you know the password for.

[fischej (Jeff Fischer)]

@glennf

You might also look at your list of devices in Apple Account and remove any old ones if they’re lingering in the list, such as via account.apple.com > Devices.

Thanks for the reminder to prune a couple old devices. FWIW, while you can see all your devices on the web site, and you can also be teased by the “Remove from account” button, clicking that button just gets you a message “Can’t Remove Device from Account on the Web”. At least, I got that for both of the devices I wanted to remove. The message does tell you to do it from an actual device (Settings > [Apple account]), which works fine.