macOS 10.12 Sierra has been out for a month now, and most Mac users have likely been prompted at least a couple of times to “Upgrade to macOS Sierra.  Get Siri and a whole lot more on your Mac”.

In the past, as Apple released their yearly Mac operating system upgrade, I frequently made a soapbox speech that included points like: Upgrading Macs from one version of the OS to another is not something I’d recommend in a production environment without a compelling reason or solid upgrade plan, historically I don’t generally consider an OS stable until Apple has released the .3 or .4 update, and being an early adopter comes with the risk of downtime.

While I still agree with all of those points, I understand times are changing, and Apple is assuming most people will blindly upgrade if prompted a few times… just like on their iPhone and iPads when prompted they need to update.  It’s just the nature of the beast.

I do however have two important tips for those that elect to upgrade to Sierra:

  • Make sure that every single application is patched to the latest version before upgrading, and while doing so also verify each application version is compatible with Sierra. If in doubt check and for compatibility reports.  Upgrading the OS, and then dealing with applications not working because they are unpatched or incompatible, is a common mistake leading to hours/days worth of frustration.
  • Make sure you have a full backup of the Mac saved to an external drive prior to upgrading (either with Time Machine or more preferably Carbon Copy Cloner). Upgrading the OS is a one-way path if you don’t have a backup, and those that experience major problems often wish they could just go back to the way things were. Having a full backup makes that possible.

Historically those that upgrade their Macs themselves often have problems with printers and scanners not working, incompatible apps, Time Machine stops working, and Apple Mail issues.  Sierra is no different.  Mail in particular seems problematic for many upgrading including: hangs when upgrading the mail database, missing attachments and signatures, and mailboxes not imported properly.