In a recent coaching session, a client summarized a key insight they’d just learned from me: Once you upgrade to a major version of macOS, keep it up to date. That is, install updates but temper your upgrade enthusiasm.
Three years ago in Upgrades Galore, I shared a few tidbits of that year’s OS versions and encouraged users to upgrade all but macOS soon after release, delaying the latter 1–3 months. This generally remains my current wisdom.
Then, once you upgrade to a major new version of any device software, I recommend you keep it up to date, installing any updates within that version series.
Client Notes
Recently, I’ve helped Rachelle, Jan, Daniel, and Srinika take control of their email accounts and advised Felix and Bruce about what new Apple devices to buy or not to buy. I also enabled Ronna and Lisa to update their iPhones using the Finder on Mac, which works wonders when one’s device lacks sufficient free space to both download an update and install it.
Plus, after recommending that Daniel invest in a Synology Disk Station to become the new digital file cabinet for his business, I started the complex setup of his new toy and will continue in coming weeks.
Finally, at the end of a nearly unplanned in-person visit, Marci shared that she’s developed a number of workarounds. With gratitude, I reflected on the value of this statement and am beginning a marketing campaign for my services around it. Exploring users’ workarounds is an opportunity to discover, learn about, and consider using apps, features, and settings that satisfy their needs with preexisting capabilities.
Automatic Updates
You might keep Automatic Updates enabled and expect that the device will regularly check for updates and offer to install them. However, I’ve found a variety of scenarios as well as specific OS versions where this process failed.
Either the update checker had a glitch; or, it successfully offered an update, the user deferred the installation, and all was forgotten. Thus, I recommend checking for updates manually about once a month. The smaller updates that come out within a major version number often include important security fixes and sometimes contain new features, too.
On Mac, iPhone, iPad, and Apple Watch, you can do this in (System) Settings > General > Software Update. On Apple TV, go to Settings > System > Software Updates.
Major Version Upgrade
Over the last 10–15 years, depending on the platform, Apple has been in the habit of delivering a major new version of each device operating system annually around September. These upgrade releases bring new features, settings, user interfaces, and sometimes applications.
How an OS displays the opportunity to upgrade is slightly different on each, especially in the last few years. On Mac, the Software Update pane shows the major version upgrade at the top with a description, followed below by any updates available for the current version. For example, when macOS 27 was released, macOS 26.7 came out the same day. On Macs supporting the former, the latter was shown near the bottom in an “Other Updates” section.
Meanwhile, on iPhone and iPad, the minor update appears at the top with its (usually short) description, followed below by a button that invites the major upgrade. This leads to the (usually long) description of the latter and the opportunity to install it.
Why Apple designs these update screens differently is baffling! If anything, I would recommend the reverse. I find macOS deserves more caution before installing an upgrade, whereas all other platforms are part of a more controlled ecosystem featuring fewer incompatibilities.
While I tend to upgrade pretty soon after public release, I maintain my recommendation to clients to defer until Apple delivers at least one update after the fact. This hopefully results in fewer frustrations while early adopters send Apple feedback that leads to valuable bug fixes.
Historically, I have published a Mac Mondays post that announces when I generally approve of an upgrade. As of this publication, that time is not yet for OS 27, but perhaps in October the upgrade day will come. If you feel otherwise, share your insights in the comments…
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