Sierra Features & Recommendations

Today, Apple releases the 13th major revision of what began life as Mac OS X, turned into OS X, and is now macOS. Sierra, macOS 12, will appear in the App Store this morning for free. The tentpole features this time out are subdued, and Sierra represents a refinement of the changes that began in OS X Yosemite in 2014, and continued in OS X El Capitan last year.

Our advice, as in previous years, is that discretion is the better part of valor, and waiting until you have a convenient time to be without your computer for an hour or so, after you’ve determined if your working application load is functional in Sierra, is the best way to proceed. This basically means we don’t recommend updating today unless you enjoy pushing the boundaries of the future. We will, of course, support you as best we are able, but our general advice is:

  1. Don’t update without a backup. If you’re not sure if you have a backup, you need to be 100% sure before proceeding.
  2. Don’t update without checking the compatibility of your applications with the new OS. Our management and monitoring systems are compatible at this time, and our tools will work with Sierra. If you’re not sure your tools are compatible, please check. We’re happy to help.
  3. Don’t update without being aware of the new iCloud features listed below, and understanding the consequences of turning them on could include data loss, or being without your data offline.

As always, we take the advice of Salah from Raiders of the Lost Ark.


Please note that we don’t mean you should go first, but rather other intrepid OS explorers, who have the correct safety apparatus and a willingness to explore knowing that loss is possible.

While Sierra is a refinement release, there are a couple of interesting tentpole features for Apple to hang its hat on. The first is the arrival of Siri to the Mac platform. Long a mainstay of iOS, Siri now has access to many of the pieces of your Mac’s environment, including your files, your calendar and your personal information. If you have internet access, Siri can perform tasks for you related to your operating system such as “Create an Appointment tomorrow at 9am to call Tom” or “Find all my emails from Tom Bridge” or “Show me all the pictures of Charlie”, and Siri can do those things. Siri can move files, send messages, and other activities.

I find Siri’s inclusion to be a novelty, and a bit of a disappointment, if only because I can’t imagine myself ever speaking to my computer in an open-plan office, or in a coffee shop, or even my home if others were around. I find the idea a talking interface to your computer to be a bit bizarre, but I recognize I may an outlier. I don’t talk to machines in public, I save my talking to people. Is that weird? Maybe. It is straight up humanist discrimination? Well, yes, it is. This is where the computers come for me, isn’t it?

The second tentpole of Sierra is one that I find both intriguing and horrifying all at once. Apple wants you to trust your Documents folder and Desktop to iCloud, and allow your local operating system to figure out what needs to be stored locally, and what can be stored in the Cloud instead. They’ve prepared us for this reality, of course, and this is just iCloud Photo Library, but applied to your Desktop and Documents folder. This is a great concept, designed to save space on your SSD-based Macs that are very definitely space constrained, but there are pitfalls. I am glad that Rich Trouton has made available his configuration profile that blocks this setting for organizations to use on their computers. I’m not interested in turning this feature on any time soon.

There is one convenience feature that I am enjoying so far, and that is unlocking the phone with my Apple Watch. This feature relies on Apple’s Wi-Fi proximity check scripts, as well as access to your iCloud account, which must be set to use the new Apple Two-Factor Authentication for security purposes. This means you’ll have trusted devices that are capable of providing a 6-digit one-time passcode for granting access to your AppleID. If your Watch and Mac are set to use the same (2FA-enabled) AppleID, the presence of the watch (in an unlocked state, on your wrist) will unlock your Mac.

If you want to learn more about the security of macOS and iOS, I strongly recommend watching Ivan Krstic’s Blackhat talk, which goes into depth about the security behind this unlock procedure (Starts at 24 minutes in). The amount of thought that has gone into this process is staggering, but I would absolutely watch the heist flick, or Mr. Robot season, that takes on trying to break it (and failing).

There are some additional features in Sierra that are of interest, but you’re likely already exposed to their arrival, as they’re in iOS 10. Photos’ Memories features and new search capabilities are on your Mac, the Apple Music experience is now available in iTunes, with enhanced capabilities, and the new iMessage types, responses and animations are available in Messages for view.

There are some additional under-the-hood changes in Sierra that are interesting, including changes to the SIP directories, locking down further portions of the underlying OS-facing file system, and the inclusion of APFS as a disk type that the OS can understand, but neither of these concern users at large, who this guidance is for.

As always, we are happy to answer your questions.

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