Before You Update Your iPhone... (or other Apple Devices in Fall 2019)

Since I first watched the Apple Software Keynote amongst my fellow nerds over the summer, I knew that Apple's Operating System software updates this year were very ambitious. The ambition became clearer during a rough beta testing season, and then with an awkward and staggered schedule to release the new software to different devices on different dates this fall*.

There are the problems with updating each device as soon as it comes out:

With these release dates all over the place, it's frustrating to upgrade your phone but not your Mac or iPad with the new software. There are many interface changes that might throw you if only one is updated. And sync on a few apps is simply broken across software versions. If you rely heavily on apps like Reminders, you're in for a few headaches if you update everything as the new software becomes available. Either you'll lose syncing between your updated devices and not-yet-updated devices, or get lots of nagging reminders to update.

And not all devices can be updated to the new operating systems. It's worth checking to see if all of yours are eligible before updating any of them.

Personally, I'm planning to wait until the week after iOS and iPadOS have both been released (first week of October). I need to have the new OS in time for some projects I'm working on, and I don't typically use Reminders on my Mac at all. And I am not sure about when I'll update to macOS Catalina-- there are some issues with plugins in Final Cut Pro and I need to make sure updating doesn't interrupt my production schedule.

TL;DR: The simplest solution:

  • Wait to update everything until macOS Catalina has been out for a few weeks. Sometime in November or December.
  • Don't impulsively install Catalina on your Mac, because it will break some software.
    • Use Go64 to test for some applications that won't work on your Mac after updating.
    • (There are also some new security requirements that are harder to detect and might cause problems.)

I want to be clear: I'm positively giddy about some of the changes coming to Apple's software. But with great complexity comes great caution? Or something like that. I think you'll enjoy the changes, too. Just don't rush it until you're ready.

*Softaware Release Dates:

Update 2019-10-03:

Still hearing lots of bug reports from folks. I'll have to update in a couple of weeks so I can finish updating my slides and videos for the International ADHD Conference, but I'm worried that some of my automations will break when I do.