When Should You Upgrade to Apple’s 2024 OS Releases

For some years now, my practice has been upgrade to the new macOS after the next macOS is released. So I’ll upgrade my secondary computer (a MacBook Pro) to Sonoma once Sequoia is released.

Normally I’d upgrade my main computer (an iMac) a couple of months later. But this time I can’t – it doesn’t support Sonoma – which means, I’ll need to get a new computer. And that means I’m stuck on this iMac until I finish all of the games that only run on Intel.

It is another Catalina situation. I was stuck on Mojave for a little over 2 years, until I finished the 32-bit games.

When I was working I’d typically wait for a .3 or .4 update before committing.

Now I’m retired - and have a couple of spare machines - I’m likely to update a spare and see how it goes. My main machine will stay on Sonoma for at least a few months unless my tests show it’s ‘safe’.

As long as the updates don’t screw up iCloud I see upgrading a spare machine as minimal risk.

Local (USB) Calendar syncing is still broken under Sequoia (and Sonoma, and Ventura), so no. This summer my iPhone also had a traumatic (fatal) impact. Seriously thinking dumb phone and DayTimer.

I may rue saying this sometime over the next month but I’ve become relaxed about upgrading even on the day of release. The long graph of reliability since System 4 () shows a steep upturn over the past 5 years. I just upgraded an iPhone, an iPad, and a Watch and so far no hiccups. I did have to fully reset the 32G iPad in order to get enough space for the install. (Hm, maybe time to upgrade. . . .)

The 2017 iMac is limited to Ventura and in the next couple of months I’ll upgrade to a Mac Mini but even with the security updates I just do them when they come out making sure it’s fully backed up before I do them (and it is fully backed up).

If you’re responsible for a farm or farms of Macs in production, for sure I would say wait for months if not a year to upgrade but for personal use? Do it when you feel comfortable but don’t obsess about it.

Dave

My reading here suggests many people wait months (or years) after major releases to upgrade. So I think it important to point out that falling behind the latest release means slipping considerably with respect to having Apple’s patches for security vulnerabilities.

Case in point… I did a comparison of the security issues patched with today’s release of iOS 17.7 vs. the release of 18. While I didn’t actually count fixes, I’d say that of all the vulnerabilities fixed in 18, only maybe 70 to 75% were also present in 17.7. While I didn’t check the comparable releases of macOS, I would expect a similar ratio.

So even with installing today’s security releases for the now “old” OS, you’re already missing some fixes for non-trivial vulnerabilities. And as the year progresses, you’ll fall even further behind.

Admittedly, I haven’t been burned by a major release in its first few weeks for quite some time. And I’m rather paranoid when it comes to security vulnerabilities. So your threat/bug model may differ considerably from mine. Nevertheless, it’s good to know some of these details and the corresponding risks when deciding on your upgrade strategy.

I wouldn’t read too much into that. It’s very possible that many of the “missing” patches were issues introduced during iOS 18 betas and aren’t vulnerabilities in iOS 17.6.1.

So far no issues for me with iOS 18 or watchOS 11.

I upgraded my iPad Pro (2021 M1) and iPhone 13 Pro to iOS 18 today. No problems at all.

I really don’t understand the math editor, or the other new Memo features. I have to find a place to read up some more on it. Everything else is working fine.

I do like the fact that they have merged Reminders into the Calendar. I’m going to stop using a third-party Calendar app now.

I haven’t tried many new features yet. But no speed or battery or heating or other problems so far. Looks nice.

I honestly don’t understand why people wait such long periods of time before updating to the latest OS release, except of course in cases where it will break compatibility with a key app. For all the bugs in MacOS, at a high level reliability these days is extremely good, the chance of a serious issue is very small. The public beta process surely helps with this. But honestly, waiting a year to upgrade doesn’t seem to serve any practical purpose. And there are often loads of little quality of life improvements in new versions of MacOS, as well as features that take advantage of corresponding ones in iOS.

I definitely understand waiting a few weeks to see if there are any major bugs that shake out. But what is the purpose of waiting a year? MacOS is simply not as buggy and more reliable than it was in the Snow Leopard days.

One solution might be to see how the games run under Whisky. I’ve only done this with one game and it seemed to work pretty well. But I’m not a gamer and don’t know how resource intensive your games are. Still, you could test how well it works on your MacBook Pro to potentially remove a dependency for upgrading the iMac.

When I picked up my iPhone 11 Pro I was intending to update to 17.7, but I was presented with an 18.0 promo that I didn’t see how to escape. So I shrugged and now am on 18.0.

I have a 2020 Intel 27” iMac and a iPhone 12Pro that can upgrade to newest OS and iPad 10.5Pro and Watch Series 5 which cannot. Will there be compatibility issues in Photos between new and older versions on my devices?

One problem found in iOS 18 on my iPhone 13 Pro with Siri.

Siri’s automatically deciding whether to use its voice or not is not working right. At night I always turn my sound and alerts off. But unattended Siri is supposed to use its voice. In the morning before opening my eyes I often say, “Siri, what time is it?” and it answers.

This morning it didn’t. I had to go into Siri settings and change the automatic (is that a new setting) to always use voice.

I tried reporting this to Apple Feedback, but there is no option to choose iOS 18 yet there.

My Apple TV automatically upgraded to 18.0. After a while one of my 1st gen Stereo Homepods stopped playing. I upgraded both Homepods to 18.0 but the problem was not fixed. I tried restarting everything but it was still not fixed.
Eventually I powered off the Homepods - fortunately this fixed the problem.

I will delay upgrading my Mac to Sequoia!

I delay to put off the pain of lost functionality as long as possible. And, since Apple moved to the annual release cadence, each release adds more bugs than are fixed. The problem is they only fix bugs that are confirmed to be new for a release. All the other bugs become “existing”, with no development time spent to address.

Last night I was given the choice between iOS 17.7 or 18.0 on my iPhone 12 and iPad Mini 6; went with 17.7. I haven’t checked my iPad Mini 5 yet because I have to keep it on 14.4.2 due to one non-replaceable app.

Edit: 25 Sep 24 I forgot to mention I’m maxed out on my iMac at MacOS 10.13.6 and on my MBP at MacOS 12.7.6

ICloud Private Relay is playing up again. I had to disable it to reach this page.

I generally update to a new macOS version about the time its successor enters the beta period - my days of always wanting the latest and greatest have long since passed

But then, I’m under the impression that most improvements these days happen in the macOS/iOS integration area, and -not using iOS- that is of no interest to me.

As I usually do, I jumped right into the deep end, updating both my iPhone & iPad to iOS 18. They’ve both been fine – basically over the last decade or so, Apple’s public beta period seems to have taken the place of the previous first few months of a system release in terms of working out serious kinks. System reliability and bugginess is so much better now than it used to be, which is great. I haven’t had a chance to play with the new features much so no word there yet.

Me too…did 2x iPad Air 4, iPhone 15 Pro Max, Watch 9, and M1 MBP 14 with no issues. My overall upgrade experience matches yours. I did wait until yesterday vice Monday to do anything just in case and backed up everything first of course.

Same - I did my iPhone and both Apple Watches on Monday, and the iPad this morning. I updated one of my Apple TVs Monday night, mostly because I wanted the updated enhanced dialog feature. I may upgrade to Sequoia on my MBA later this morning, too.

Really iOS and iPadOS are fairly minor upgrades with 18.0. The enhancements to watchOS (plus fitness on iOS) I really like, though it’s going to take a while for training load and vitals to start giving me reports (which seems weird, since I have history already in the health app.) Coincidentally I am now ill (first symptoms Monday night) and the vitals app reported this morning higher heart rate, breathing rate, and wrist temperature than normal, so that’s good to see. That said, again, watchOS 11 is not a dramatic upgrade from 10.

That’s my go too when my HomePods (original ones) decide to be trouble. Unplug them for a couple of minutes. They always reboot fine.

I got that too, the choice. Actually I think that’s the first time I ever saw that.

Mine is a production Mac and it takes a while to check App compatibility and whether anything critical is going to break somewhere in the chain, and that might not be due to the OS itself but the ramifications across the board, including peripherals. I normally review bug reports until the Spring when I am clear about what the various pros and cons will be and what solutions have been developed and tested.

The trend has been for macOS updates to be less disruptive than in the past but there is little urgency and changing workflows can be time consuming and aggravating, so picking the right moment between projects is the key for me.

I also need to test compatibility with client systems and they update their Macs when I give them the all clear and I know what configuration changes may need to be made. They don’t like updates much, so no pressure coming from there.

I fall on this side for the most part. A lot of the changes that come about with each major release feel to me like changes for the sake of change. So I wait until I know I will have time to spend getting used to the changes and updating the myriad third-party apps that inevitably break with a new major release—especially with iOS/iPadOS apps, which still have to work their way through Apple’s App Store review process. Despite compatible versions having been submitted by the developers, Apple may not have posted the updates to the App Store yet.

Third-party apps and devices are a big stumbling block for many people. For example, I use a Freestyle Libre continuous glucose monitor (CGM) for my diabetes (well, I did until the sensors got backordered this month—now I’m considering switching to a different brand). The hardware readers for these sensors are pricey, even with insurance, but the mobile app makes a hardware reader superfluous for most people.

But.

Abbott (the company that makes Freestyle diabetes products) still doesn’t even officially list iOS 17 as fully compatible with their app, such that when you first run it on iOS 17, it makes you confirm and accept that some features may not work correctly because it’s an “unsupported” OS. I’ve never had any problems I could trace to this, but it’s still annoying to have such an incompatibility this long after iOS 17 was released. I got an email from Abbott the other day warning that, similarly to iOS 17, they cannot guarantee full compatibility with iOS 18, and they recommend waiting to upgrade.

Then there’s the history of major bugs in initial releases, which, while not nearly as common as some people think, are still common enough to be a consideration; honestly, a single data-destroying bug in ten years is frequent enough to be worth pausing before the update. Public beta testing will never catch all possible major bugs, because the number of configurations (hardware + apps) is effectively infinite, and the number of users willing to test out a public beta is still a small fraction of the total user base. So it’s prudent to wait at least until the initial bug reports start rolling in, typically within a few days of release, if not to just wait for the inevitable x.0.1 release that should fix whatever big things may have gotten missed in beta.

OWC recommends that anyone using SoftRAID update to Sequoia.

There is, in fact, such a bug in iOS 18 (though based on what causes it, it’s probably rarely triggered.)

In the messages app if you are part of a message thread that receives a watch face attachment shared from the watch app, replying to the message can cause a crash when opening the thread that can be fixed only with a deletion of the chat history of that thread.

https://9to5mac.com/2024/09/18/ios-18-messages-app-crash/

I’m just behind the bleeding edge. I usually don’t upgrade to betas and never for critical devices (my desktop Mac, iPhone, and iPad). I generally advise my more risk-averse friends to upgrade several months afterward when there appear to be no more severe bugs or new features), but I insist that they do it before the next full-version production release.

I do that because getting informal support from me is harder for older versions. By the time the next version has come out, I have forgotten the changes between older versions. I also have difficulty remembering what issues caused problems during the upgrade. It’s harder to research the issues and to get support from Apple.

Skipping versions means that when you finally do an upgrade, it will be even harder to troubleshoot issues that arise.

I’ve been upgrading with initial releases for many years and haven’t had any data loss. This is a shift from previously when things were less solid and I did wait until a few point releases were out. Obviously that’s just me, so take it fwiw.

(On the other hand, in this media world, any bug is going to get breathless and horrified wall to wall coverage, so take that fwiw)

I have upgraded none of my Apple devices yet. The iPhone, M1 Max and Watch I am waiting for a period where I can thoroughly learn the new functionality. For me, this is a positive thing. Going through all new things and finding the nice things that make a difference for me. I see a period coming up in about 2 weeks.

I generally wait a week or so to do a major update to avoid the issues we’re seeing reported this time around: iPadOS bricking the M4 iPads, crashing but in Messages if your reply to a thread with an Apple Watch screen, etc.

In these cases, I’ll wait for the bug fix releases and then another week or so to see if they work or not.

Kevin

I updated my iPhone 13 Pro and iPad Pro M1 to iOS 18 a couple of days ago and basically they are ok. I like the new way they merge reminders with calendar.

I don’t like some things in Photos, like the new organization, or the way movies loop and don’t just stop when done.

But no bugs.

And… I took the leap and upgraded from MacOS 14.7 to Sequoia just before! This is on my MBP 14" M1 from 2021. From initial request to finish and login was just 35 minutes. I don’t see any problems so far. All my apps reopened. And one piece of good news! A problem I’ve been having lately with Microsoft Word, where I couldn’t drag my cursor and select text, was fixed with the upgrade!

So basically no problems… so far.

Here’s more about the iPadOS 18 and M4 iPads—Apple has apparently pulled the update for the moment.

https://9to5mac.com/2024/09/17/ipados-18-m4-ipad-pro-bricked/

This is exactly why some of us will never update right away. Thanks to all those who do though, that’s how we know when to continue to hold off.

On Monday I upgraded my M1 MacBook Air and M2 MacMini to 15. I upgraded 4 HomePods to HomePod OS 18, an AppleTV to TVoS 18, my 15 Pro to iOS 18, my Ultra to WatchOS 11, and my iPad mini to iPadOS 18. I’ve had no problems at all. The only thing that doesn’t work as it’s supposed to is iPhone Mirroring, and my 16 Pro arrives tomorrow, so I’ll try again once that’s up and running. Maps on iOS/macOS/WatchOS now have trails (at least most of them), although still no topographic maps as was promised last year (except for one small patch on my Ultra). And for some reason my Ultra seems to charge slower that it used to on the 3rd party charger I use. Haven’t looked into that much yet.

You’re welcome! We initial adopters appreciate y’all not clogging up the server bandwidth.

Luckily my iPad Pro M4 did not brick with the update. I wonder what the factors are that bricks one but not another

I think you also should take into consideration what kind of Mac processor is in your machine. If you are running and Intel Mac, many new features in the past two macOS upgrades did not apply to your machine. Even that warning from OWC for Softraid users applied to Apple Silicon users. Right now, I suspect the majority of the people in system development at Apple are concentrating on getting things right for Apple Silicon. I have seen this play out for the transition to PowerPC and from Motorola to Intel. Each time, you were best off to leave the older computers on legacy systems. System 7.5 was the best for 64000 series, all the system 8 versions were bug ridden and System 9 was PowerPC only. Tiger was best for PowerPC, Leopard actually lost features like Classic! Monterey has been very stable for my iMac and all my Intel software is running latest versions. (I’m one version behind on Pages - I not missing anything I use.) When the software I use won’t run on Monterey, I’m pretty certain they won’t run on Intel. For those worried about hackers, Apple AI is a huge target - and my iMac is immune. For those with Apple Silicon, you are on the other end of this. You have been stuck with releases like Mac OS 8.0 and Cheetah. It takes a long time for Apple to get things working well on the new hardware. Snow Leopard was pretty sweet and so is Mojave. Sequoia certainly sounds like it is mature - I hope the name choice can meet the big expectations.

I did all mine (Mac Studio, and iOS devices along with Homepod). Then this morning, doing remote work from home, my “work” MacbookPro offered the Sequoia update. I thought, OH, Jamf admins are ok with push for this. It updated fine.
Then I read some computer news and … drop jaw. Seems Crowdstrike and Sentinel One are breaking Sequoia installs. GREAT! So sigh… since this was posted today (9/19/2024), I will check in the morning with our group on why this was ok’d or if they have the updated Crowdstrike resolution.

I got a bit annoyed with SoftRaid when they went the subscription route (and also an issue with getting my license to work on a different Thunderbay enclosure). I’ve actually started using Apple Raid on a non-critical backup to test it out. No issue after about 6 months.

Do you have any links or information to back up this claim? It’s the first I’ve heard of this, and I can’t think of any obvious reason why Apple AI is going to be less secure than the rest of the OS.

That wouldn’t work because the emoji would then be too large compared to non-emoji characters. Line spacing would be messed up and the text flow would generally look bad. Emoji are supposed to be inline with text, not graphics that affect the text layout.

I’m finding the re-worked Health app on the phone… confusing (to say the least). They’ve tampered with things which weren’t broken.

Also, my custom watch face has been replaced with some face I’ve never seen before. Surely the fact I’ve customised a face suggests that’s the one I want to use. Update: Apple have deleted several of the original Watch faces. I absolutely hate Apple today.

Annoying!

Looks like Panorama X users should hold off on upgrading to Sequoia for a bit.

With macOS, I always wait until at least “X-dot-1”. At this time, 14.7 works just fine and I’m not tempted by yet more options in “15-dot-zero” in Apple’s never-ending “feature-bloat parade”!

That’s like the old rule for DEC VAX VMS updates. You only installed even number releases (.1, .3, .5, etc.)

I’ve held off on both Mac OS and iOS new versions, but did install iPad OS on one iPad. The one problem I’ve noted (posted elsewhere) is with ads going full-screen if I happen to roll the mouse over the ad. That’s VERY ANNOYING to say the least.

It’s also standard in the Linux kernel world (and many other areas). By convention, even-numbered releases are fully supported, while odd-numbered releases are development/alpha/beta versions.

If 1, 3 and 5 (to use the examples given) are even numbers in the Linux world, it’s even more curious (I almost wrote “odder”) than I’d realised.

There’s now a fix for the Panorama X problems with Sequioa.

One cool feature in MacOS 15 and iOS 18. A WhatsApp notice appeared on my Mac. I clicked it and my iPhone mirrored on my Mac with the WhatsApp app open and I could read and reply. I didn’t even have to touch my iPhone. Sort of nice.

Same here EXCEPT my main Mac is a Mid-2011 iMac so it is maxed out at MacOS 10.13.6 High Sierra. I CAN’T replace it until I can find a replacement for a CRITICAL (to me) application the developer of which passed away in May 2013. I also have a mid-2015 MacBook Pro which itself is maxed out at MacOS 12.7.6 Monterey. I did have to purchase a refurb 2022 MacBook Air M2 with minimal storage and memory for use with my tax software that effective this month requires MacOS 13 Ventura minimum. However being on a fixed income now I can’t buy a new iMac (though I DID splurge on an iPad Mini 7).

There is a developer that is working on an iOS app that could replace the 2013 application on the iMac while running on an Apple Silicon iMac so hopefully that may be a solution eventually.