Apple’s Two Factor Authentication

Apple released macOS Sierra earlier this week, and I installed it via the App Store on my MacBook Pro. As always the installation was smooth and uneventful. This has always been Apple’s strength making the upgrade process as seamless as possible.

The upgrade came with many new features. Syncing contents from the Desktop and the Documents folder to my other Apple devices sounded very attractive. Unfortunately, Apple will have to earn some additional credibility in this department before I fully trust this feature. Before I entrust my most important data sitting in my Documents folder to an automated process made by the same makers as iCloud, I like to see some good history being made first. As for remote copy and paste, I’ll get around to it when I actually have a use case. The tab feature is also another use-case specific feature. Check out this article from for a more thorough list of the new features.

There are only two features that I really wanted out of this new version of the operating system.

  1. Siri on the desktop
  2. Allow Apple Watch to unlock my Macbook Pro

I used Siri to open applications, perform web searches, and do other things that I do with Siri when I use it on my iPhone. It was pretty impressive and handy.

I thought being able to unlock my Mac with my Apple Watch is a very cool trick. Apple explained it on one of their support pages. When it came time to explore how to setup the auto unlocking feature with my Apple Watch, I learned something new. One of the requirements for the auto unlocking feature is Two-Factor Authentication. Unbeknownst to me, I have been using an older form of authentication called Two-Step Authentication. The folks at did an excellent job in explaining the differences.

I went about converting my Apple ID from using two-step authentication to two-factor authentication. This process is not so straightforward. There were some scary moments when iCloud settings failed to setup correctly, or verification codes were not received. Finally, I overcame all those issues through reboots and retries and having multiple iDevices and Mac’s during this process came in handy as well. I can see how novice users can lock themselves out of their iCloud accounts when subscribing to two-factor authentication in the beginning or when transitioning from two-step authentication.

After successfully converting to two-factor authentication, I turned the auto unlocking feature on in the Mac’s Security & Privacy preference pane. On the first try, it had an issue pairing with my watch. The second attempt solved the issue.

In my case, the most confusing part was that there were just too many credentials to keep track of during the setup process:

  • iCloud password
  • iPhone passcode
  • Mac login password
  • Verification codes that Apple sends to your trusted devices

For me all were different. Just beware that you really have to read the prompt and make sure you are providing the correct information during the setup. At least I feel a lot better using Apple’s latest authentication mechanism with a 6 digit verification code versus the previous less secure 4 digit code. Also if you sign up two-factor authentication with your iPhone, you may have to ask Apple to send it via SMS, because your messaging and notification may not be working yet.

When you switch to two-factor authentication pay attention to what information you provide. Good luck to those who try!

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