A checklist for IT pros waiting to deploy a new macOS

It’s mid-September—the arrival of football, foliage, and another new Apple operating system for CTOs and IT leaders like Kevin Dulaney to test.

Apple has officially released the macOS Tahoe 26, with updates including transparent taskbars, new search functions, and AI-powered shortcuts.

Dulaney, EVP and head of technology and innovation for SourceCode Communications, supports about 50 MacBook machines at the company. Like many Mac admins, he has to ensure that updates don’t break critical applications.

IT Brew spoke to Dulaney and other Mac pros about their general test methods when deploying a new OS—and what they’ll be watching for in this one.

Feature presentation. Apple released beta versions of its macOS 26 Tahoe in June, spent a few months gathering feedback and tweaking the code, and then issued the updated operating system to the general public on September 15.

Dana Stibolt, president and founder of Apple reseller, service provider, and consulting firm MacMedics, offered warnings for an admin firing up a new macOS on employees’ machines, especially if they’re relatively new to Apple’s ecosystem:

• Make sure you have enough space for the upgrade.
• Have a Time Machine Backup in place.
• Don’t install a new OS over one that’s already having problems. “You may have a problem with your hard drive or some kind of underlying hardware issue, and adding a new variable can be troublesome,” he said.
• And, generally speaking: Wait. “Do not install a new OS if you’re in the middle of a big project or a deadline, and double-check that the app that you do your work in is fully compatible with the new OS.”

Testing, testing. Dulaney keeps a pair of test employee machines nearby—an older and newer version—to run the latest OS. During a fortnight-or-so test period, Dulaney makes sure business-critical applications work, and they don’t require any specific security permissions.

“There’s nothing worse for an end-user than coming in one day and stuff’s not working,” he said.

Even simply opening and closing programs on a test computer, he said, can help spot unexpected breakages, especially with graphic-intensive apps like Adobe Photoshop.

One macOS 26 Tahoe feature that Dulaney will be excited to investigate: search-bar upgrades. Mac’s all-around thing-finder Spotlight now lists results like files, folders, and apps together, “and intelligently ranks them by relevance to you,” according to Apple’s support documentation.

“I use the search bar and Spotlight for almost everything I do when I need to find something quickly,” Dulaney said.

Spotlight is “now contextually aware,” and able to understand apps and text to provide suggestions and shortcuts, including summarizing text and creating images.

With macOS 26 Tahoe, Apple also included iPhone mirroring, enabling a nearby iPhone’s live activities to appear on a Mac.

IT pros may have to consider the security impacts of this feature. “They may want to turn off the iPhone mirroring feature so that personal data is not commingled with corporate data,” Stibolt said.

Dulaney will be monitoring performance impact of the Apple Intelligence features, in particular. He wants to understand: Is it stealing cycles off the processor that could be used for other tasks, such as creating a graphic or pulling research data?

“What impact is it having on my overall experience that my users are going to notice, and do the features that it is bringing outweigh the productivity it is going to bring to them?” he asked.

Ranjit Atwal, research director in Gartner’s Quantitative Innovation team, considers Tahoe “a major upgrade” compared to previous releases: “This is the first Apple device on the PC side that will be tested for [its] AI features,” Atwal told IT Brew.

As is standard procedure with new macOS features, Dulaney has any new AI assistance feature turned off for now—at least until testing season ends.