When your Apple device refuses to be trusted

Back in July, I received a new Macbook Pro.  A lovely little device, but I had this one problem.  It wasn’t showing up as a trusted device under my iCloud account. 

When you log into a site or a service that requires Apple’s 2 factor authentication, you can use a Trusted Device to generate a 6 digit authentication code.  Most people use their iPhone, but I don’t have an iPhone.  Plenty of other Apple devices, just not the phone.  And 2 factor authentication works on my iPad, my old Macbook, and my Mac Mini.  Just not on the new Macbook. 

The 2 Factor Auth prompt

When I’m travelling, the only Apple device that I carry is the Macbook.  When I log into a service that needs the Apple auth, I want to be able to use my Macbook to provide that code.  That’s a pretty reasonable request.

This is what you should get

This has been frustrating me for a good month or so.  There is no switch or setting to enable.  Once you enable your iCloud account on an Apple device made in the last few years, that device is now a trusted device. That’s all you are supposed to have to do.

Except for my new Macbook.  It would not display the dialog that would prompt for the authentication code.  I tried Apple Support via email, but that proved to be fruitless.  I don’t think that they fully understood the problem.  I tried again today with Apple Support via phone.  It took the better part of an hour, but we finally resolved the problem.

Basically everything was setup correctly and should have worked.  But it didn’t.  With anything computer related, sometimes the best solution is to nuke the problem from a Low Earth Orbit.

It’s the only way to be sure

So we removed the iCloud account, rebooted, and added it back again.  That resolved the problem.  The Apple Support rep thinks that the iCloud auth token on the Macbook was corrupt. I have no idea how or why that happened, but that would explain what caused the problem.