When Should You Should Upgrade to macOS 15 Sequoia, iOS 18, iPadOS 18, watchOS 11, tvOS 18, and visionOS 2?
September is here, so Apple will soon release major upgrades for all its operating systems. iOS 18 and watchOS 11 will undoubtedly ship alongside new iPhone and Apple Watch models likely the week of September 16 (we'll find out exact dates tomorrow). iPadOS 18 is likely to accompany iOS 18, as are tvOS 18 and visionOS 2. Although Apple has sometimes delayed the release of macOS until later in the year, rumors are that Apple will release macOS 15 Sequoia earlier this year, probably with its siblings. So we might get all of the major upgrades at once in another week.
Apple previewed these releases at its Worldwide Developers Conference in June, and many people have been testing the public betas since. Once Apple judges each of its operating systems to be ready for public consumption, the question arises—when should you upgrade?
Note that I say when and not if. There’s no harm in delaying a major operating system upgrade until Apple has sanded off any rough edges that slipped through testing. But waiting too long puts you at risk from security vulnerabilities, increases compatibility annoyances, and prevents you from taking advantage of new features. Plus, when you buy a new Mac, iPhone, or iPad after these operating systems have shipped, you’ll get the latest version, which could pose problems for your existing apps or compatibility with older hardware or workflows. If you have to replace a device it's always smoothest when both your old and new device are on the same version.
Given that we don’t know precisely when each operating system will come out, here’s my recommendation for the general upgrade order that I anticipate and how long I suggest waiting after the release appears. I also share a few new features that might encourage you to upgrade, assuming you have a device that’s new enough to take advantage of them.
Remember, always make a backup before upgrading a Mac, iPhone, or iPad in case any unexpected problems arise. It has been years since I've seen any major problems from an upgrade but you should have a backup anyway and now is a good time to check on that.
iOS 18
It’s usually safe to upgrade iOS fairly quickly because Apple puts significant effort into ensuring that the new iOS version is a good experience for those who buy the new iPhones that come with it. However, because iPhones are so crucial to our everyday lives, it my be prudent to delay the upgrade to iOS 18 for a week or two, just in case. After that, you can install it and enjoy the new features.
Even before the Apple Intelligence features start appearing in iOS 18.1, there’s plenty to look forward to in iOS 18. Messages via satellite will let you stay in touch even when there’s no cellular or Wi-Fi service. You’ll be able to personalize your Home Screen layout more by placing apps and widgets wherever you want. App icons and widgets get a new Dark look, and you can even tint them all a certain color. Keep prying eyes out of sensitive apps by requiring Face ID to open them. You can now rearrange and resize controls in Control Center, plus create groups of controls accessible with a single continuous swipe. You can even swap out the flashlight and camera icons on the Lock Screen for other controls or replace them with your preferred camera app. Photos has been redesigned (and simplified after public outcry during the beta). Messages lets you use bold, italics, underline, strikethrough, "send later", and the ability to send tapback responses with any emoji or sticker—it’s a great way to respond quickly to messages. Maps gains topo maps and trail networks, including all US national parks, and a new Passwords app makes it easier to access your saved logins and WiFi passwords.
Apple Intelligence features will start shipping with iOS 18.1 and will continue appearing in new versions throughout the coming year. They include cleanup tools for photos, notification summaries, email summaries, a smarter Siri, categorization in Mail, writing tools that correct your grammar and summarize composed text, and generative AI image creation—you’ll even be able to make your own emoji. These features will require an iPhone 15 Pro or iPhone 15 Pro Max; it’s expected that all the upcoming iPhone 16 models will be compatible. Apple has stated that the reason for this is that it requires a device with at least 8GB of memory.
watchOS 11
After you upgrade your iPhone to iOS 18, there’s no reason to delay upgrading your Apple Watch to watchOS 11. Few of the changes are likely to require significant adjustments in your usage patterns, and some may be quite welcome.
When you wear your watch overnight, the new Vitals app displays your heart rate, respiratory rate, wrist temperature, blood oxygen (on units that have it enabled), and sleep duration, showing a typical range and identifying outlier metrics. You can now adjust Activity ring goals for every day of the week or put your rings on pause if you need to take a break for any reason. The Activity app now shows your training load so you can adjust the intensity of your workouts. The Smart Stack interface now includes Live Activities and has been improved to be more intelligent, suggesting widgets based on time, date, location, and daily routines. Finally, Apple enhanced the Photos watch face to select photos automatically, optimizing the subject’s position with the frame and creating a sense of depth. Its Dynamic mode shows a new image on every raise of your wrist.
iPadOS 18
My general advice is that it’s OK to install iPadOS 18 shortly after it ships. For the most part, iPadOS is a variation of iOS, so if you’re comfortable upgrading to iOS 18, think of iPadOS 18 similarly. The main caveat is when you rely heavily on a particular app. In that case, check with the developer to ensure your app is compatible before upgrading.
Along with most of the features in iOS 18 that aren’t specific to the iPhone (like Messages via satellite), iPadOS 18 finally gains a Calculator app that goes well beyond the basics, offering the Math Notes feature that solves equations written with the Apple Pencil. The Notes app gains live audio transcription, styled highlighting, collapsible sections, and Smart Script, which refines your handwriting to be smoother, straighter, and more legible. You can also paste in typed text, correct spelling inline, touch and drag to reflow text, and scratch out writing to delete it. A new tab bar at the top of the screen promises to provide easier navigation in apps and quick access to app sidebars.
tvOS 18
Regardless of when Apple releases tvOS 18, it’s safe to update within a week or two of release, depending on the level to which you depend on your Apple TV.
tvOS 18 introduces several notable features to enhance the Apple TV experience. InSight provides real-time information about actors, characters, and music from supported Apple TV+ content, similar to Amazon Prime Video’s X-Ray feature. Apple updated the Enhance Dialogue to provide greater vocal clarity for a broader range of speakers. Subtitles have also received enhancements and now automatically appear temporarily when you mute the TV or skip back, or when content is in a different language. People with projectors will appreciate the added support for the 21:9 aspect ratio. New screensaver options include Snoopy and Woodstock, Portraits, and scenes from Apple TV+ shows.
If nothing in that list encourages you to upgrade as soon as tvOS 18 ships, let your Apple TV upgrade itself when it gets around to it, assuming you have automatic updates turned on in Settings > System > Software Updates.
visionOS 2
Since the Vision Pro has been out for less than a year and hasn’t seen widespread adoption yet, most people can upgrade to visionOS 2 shortly after it comes out.
The promised new features should enhance the overall Vision Pro experience. New hand gestures let you open the Home View and Control Center more easily. You can also personalize the Home View in a manner similar to moving icons around on the iPhone Home Screen. The Mac Virtual Display feature now supports an ultra-wide display equivalent to two 4K monitors, making it more useful for travelers who need a lot of screen real estate on the road. Beta testers have praised the new capability to convert 2D photos to 3D spatial photos. SharePlay in Photos lets you and other Vision Pro users on a FaceTime call share and interact with spatial photos, videos, and panoramas. There’s a new Bora Bora environment, and whatever environment you’re in, your Magic Keyboard or MacBook keyboard appears in front of you to ease typing. Finally, the Guest User feature now saves your most recent guest’s eye and hand data so they can skip the setup on subsequent uses.
macOS 15 Sequoia
For most of us, the hardest upgrade decision revolves around upgrading your Mac to macOS 15 Sequoia. macOS is far more complex than iOS. Mac apps are often more complex than iPhone apps. Apple doesn't have a review process to make sure that Mac apps follow guidelines, so some Mac apps do things in non-standard ways that break when the computer's system software updates. And Mac apps aren't encouraged to offer free, automatic software updates in the same way they are on iPhone, so it's much more likely that you are running an older software version that hasn't ben updated for compatibility.
If you only use basic apps like the built-in ones, Firefox, Google Chrome, and Microsoft Office, you should be able to upgrade pretty much right away. If you rely on any specialty software such as Adobe Creative Cloud or AutoCAD you will definitely want to check their support site or social media channels to see if they are compatible. They may require you to install a patch or upgrade to a newer version.
While most show-stopping bugs will be sorted out within the first days or weeks, if you are the sort of person who is annoyed by little glitches you may want to consider waiting until the end of this calendar year to upgrade.
What capabilities does Sequoia promise? The big one is iPhone mirroring, which will let you view and interact with your iPhone right on your Mac screen. iPhone notifications can appear on your Mac, and later this year, you’ll be able to drag and drop files, photos, and videos between your Mac and iPhone. New window tiling features make it easy to arrange windows in side-by-side tiles on your desktop by dragging or using keyboard or menu shortcuts. Those who do video calls all day will appreciate background replacements and a presenter preview that shows exactly what you’ll share before displaying it to everyone. The new Passwords app appears on the Mac and syncs securely across all your Apple devices. And you’ll enjoy the same updates to Mail, Maps, Messages, Notes, and Photos as are in iOS and iPadOS.
If you are unsure of when to upgrade, please book an appointment with me!
(Featured image by Apple)