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K-12 Schools: When should IT departments install iOS 14?

Most tech communities spend the summer working through the iOS and macOS betas ahead of the fall releases. For something that’s been happening for the last few years, it feels like fall software releases have been part of our lives for decades. As fun as these updates are for general consumers, they can be a significant source of stress for IT departments. As you work through these beta updates to verify compatibility, you’ll want to plan how you will roll out these updates to your inventory. If you are wondering when to install iOS 14, read on to here my testing plans.

About Making The Grade: Every Saturday, Bradley Chambers publishes a new article about Apple in education. He has been managing Apple devices in an education environment since 2009. Through his experience deploying and managing 100s of Macs and 100s of iPads, Bradley will highlight ways in which Apple’s products work at scale, stories from the trenches of IT management, and ways Apple could improve its products for students.


So far, the iOS 14 (including iPadOS 14) betas have been very stable in my experience. I still haven’t upgraded any of my Macs to macOS Big Sur, but I plan to upgrade once Apple releases a public beta. Every year, I have a clear set of testing steps that I run through before releasing the updates through my mobile device management system.

iOS testing

On the iOS side, it’s a little easier for testing. While we have hundreds of apps in our library, there are under ten that are mission-critical that we must have working every day. As I go through the summer, I watch their update logs to make sure they see regular updates and watch their support forums for beta information. I’ll test these apps with my devices to make certain critical aspects of them still work.

We rely on AirPrint for printing from our iPads, so with each beta round, I’ll make sure the printing functions we use are still working. Since AirPrint is driverless, we’ve never run into an issue, but I always test again.

On the device management side, the vendor I use always supports zero-day support for all of Apple’s new updates, so I always trust that they will be ready to go. Even though I still feel confident that I could release a significant new version of iOS on day one, I will generally wait until the first bug fix update before pushing it to our iPad inventory.

macOS testing

macOS testing is much more complicated compared to iOS testing because macOS is a much more complicated system, and there are always more things to test. The first thing I will check is how our printers perform with the latest updates. The past few updates have been super smooth with printers, so I hope macOS Big Sur is no different. We use Xerox printers, and one of their selling points is fast compatibility with new operating systems.

From there, I’ll move to test our workflows for critical applications. Even though we use many web apps, there could be compatibility issues with the latest version of Safari or with Chrome on the latest version of macOS. I will test the steps we take to process new students, process tuition payments, etc.

We use several USB hubs and video adaptors in the classroom, and while a software update shouldn’t affect them, I will still test all the various models. One of the critical parts of my testing is making sure our USB to ethernet adaptors will work without requiring a driver update, and if they do, I’ll reach out to the vendor we use.

After I do all of this testing, I feel confident in our compatibility with a new major update to macOS. Like with iOS, I will still block it from being installed on the first day, though. It’s not that I don’t trust my testing, but instead, I don’t want my users going from the most stable version of a macOS version to the least stable of the next one. I will block it for 90 days and hope that Apple releases the first major bug fixes that we can go straight to when we upgrade.

Wrap-up on when to install iOS 14 and macOS Big Sur

What is your strategy for your device updates? Am I missing anything with my testing? What are your concerns for iOS 14 and macOS Big Sur updates for the fall? Let’s discuss in the comments.

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