We have a Mac which is still on Catalina and I want to catch it up.

I had planned to update it to Monterey first (skipping Big Sur) and then in a few months go to Sonoma (skipping Ventura) when Sonoma stabilizes.

But now I’m wondering if it’s better to go to Ventura (skipping both Big Sur and Monterey).

In general, is it safer to update an out of date Mac “all at once” just catching up to the latest? Or is it better to install the interim versions?

  • PS, I just wanted to update this question, to say that I did go ahead and update our Mac, straight from Catalina (latest version I believe— but no longer considered supported) to the latest version of Ventura (13.6). The update appeared to have gone smoothly, and as yet— knock on wood— I have not seen any issues. Hopefully this will remain the case. Thank you everyone for advice!
    – pz99
    Sep 25 at 6:34
  • PPS, I should add, our setup and usage of the Mac are quite conventional, nothing unusual. Given some of the other comments more caution may be needed in unusual setups. I did do Time Machine backups (though given some people have trouble with TM restores I wondered if I should have done, say, Carbon Copy Cloner or similar too.)
    – pz99
    Sep 25 at 16:45

8 Answers 8


Here's my take on the situation in general for anyone, and you, to consider.

  1. You should always have regular backups - they are key for "undoing" an upgrade if you discover something specific to your situation that makes any upgrade problematic.
  2. You should especially have a backup, since upgrades are when software corruption or incompatibilities more often present themselves.
  3. I need a very good reason to not update to the latest. The only good general reason I have is to wait a week for the new fall upgrade - if I don't have experience with the betas, I'll pause just in case support is slammed or something gets put in "at the last moment" that was unexpected or not really tested deeply. Other than that - there's no reason not to update for security or feature sake.

For you specifically, I would focus on your backup, make a download of the current installer and make sure you're ready to erase and install - then have fun with whatever update you choose for your Mac.

  • In your specific case, you list no apps that are incompatible with either OS - so that’s the only specific reason why I wouldn’t go to the latest. Even then, I’ll have to think hard about finding another option if it keeps me off the latest for an extended period.
  • Once your hardware is dropped from the latest, then you are free to surf a stable version or if a major tool is end of life - those are good reasons to make a virtual OS or leave some hardware behind on the update train - but I try to keep all my personal / day to day work off those special case Macs.

There's nothing big problem-wise on any of the releases you mention, and the security updates on the latest are very compelling - get on the recent train for security's sake is my specific advice for you.

If you’re interested in macOS Sonoma, here is a very well presented case for deciding to upgrade on release day.

  • Thanks for the link to hoakley's blog. It's tempting advice, but the last paragraph has left me confused... is he suggesting one upgrade immediately to avoid having the early adopter label hung on you??
    – Seamus
    Sep 14 at 21:55
  • 2
    @Seamus I think Howard means to turn off automatic updates in case Apple releases the upgrade as an update. He doesn’t want people to upgrade before they want is my interpretation of the final paragraph.
    – bmike
    Sep 14 at 22:15

Why would you bother? Installing a new OS always comes at a slight risk. One time I managed to have to get acquainted with Time Machine (there was a glitch in one of my HDD's sectors which stuck the upgrade midway).

Time Machine worked like a charm. Do your backups.

There is no benefit to doing it more than needed. Macos is thankfully very stable in its UI and configuration, but do you really enjoy having to discover the few little bits that have changed in releases that you will soon leave behind?

Jump to Ventura which is very stable by now, before the brand new Sonoma is the default.

Then wait for a few months till you are 200% sure all is stable on Sonoma (i.e. the point release). I am a very big chicken myself when it comes to these things. Let others blaze the trail for you.

  • I always wait until the following OS is released. Since Sonoma is about to be released, it would normally be time to start considering Ventura. Of course, I've already determined there's no reason to bother with Ventura. Sep 14 at 1:24

You usually don't gain anything by installing the intervening versions. There was to my knowledge only the one issue where only High Sierra installed a particular bootrom update with support for certain SSD's, but that was a long time ago.

  • 1
    Mojave too… also way in the past now.
    – Tetsujin
    Sep 13 at 18:25

As a data point in favour of incremental upgrades, I recently updated from Catalina straight to Ventura and had some pretty major issues involving it hanging on startup after the install.

The issue seemed to be related to an external partition that I have and some related filesystem upgrades that were not compatible with the change. The suggestion from IT was that I should have upgraded sequentially to reduce the chance of this happening.


In general, is it safer to update an out of date Mac “all at once” just catching up to the latest?

The only real 'risk' in upgrading your OS is whether your existing third-party software will run on the new version. Software that is contemporary with OS version N will probably work fine on OS N+1. However, running that same software on OS version N+4 may well cause issues.

Mac App Store apps will automatically notify you of updates for a new OS; and even install themselves invisibly, if you want. Other software may check for updates; some may even require a paid update. But, you need to check what you have installed, and what the latest versions are.

The things that usually cause problems (rather than just crashing ;-) ) are not apps, but "other things", like drivers, and background processes that have been installed to run silently.

I'd suggest that its 'safer' to keep reasonably up-to-date with your OS -- perhaps stay on Ventura until Sonoma .3, then keep up with Sonoma until the next OS is on .3 -- than it is to do large jumps very rarely; but there's no benefit to 'working through the gears'.


I'll tell you the view of a software developer: We don't like testing on many different OS versions. Today, we test on MacOS 14 beta but only to avoid bad surprises when it is released. We assume you have a late version of MacOS 13, that would be MacOS 13.5, but if you have MacOS 13 you should have 13.5.2. Any earlier version, we assume you have the latest. On iOS, we assume you don't run iOS 13 or 14 because any iPhone capable of running iOS 13 or 14 can run iOS 15.


Monterey is the highest version supported by some software (eg: the Drobo drivers I rely on). Updating to that with a backup would give you a checkpoint for restoring to, if you would be OK keeping the machine at that level.

If you think you have to ultimately go to Sonoma regardless, I'd wait until the first point release then go to it directly.

  • Drobo is still a thing? My data was worth more to me than using a Drobo. Sep 13 at 21:42
  • I've been a very happy Drobo user for many many years, on my 2nd - bought a replacement 2nd-hand after orginal Thunderbolt version's power supply croaked. Provided you replace drives when it flags them, it just sits there and works. 16TB.
    – Andy Dent
    Sep 14 at 4:55
  • That was certainly not my experience. Given that Drobo is a dead company, might be better to transition your data to some other hardware. Sep 14 at 13:55

I will add a slightly different perspective on the answer. As others mentioned, updating the software comes with slight risks of corruption. Upgrading multiple times compounds those risks.

My strategy is to periodically wipe the system drive, OR get a new drive, and install the OS from scratch. In my own experience, and when troubleshooting other's computers, it's probably more common than people think that they have ever so slightly corrupted systems that lead to unusual bugs that are impossible to pinpoint. Wiping the system and reinstalling can fix those.

Yes, it takes some extra time to reinstall your software and files from backup (using a separate drive for that makes it a bit easier), but it can result in a more stable computer.

(Of course buying a new computer every couple of years accomplishes the same thing, but costs a little bit more.... ;)

  • 1
    Now that the OS is on a signed, read-only volume, at most you only need to erase all user data. And of course, if your backup is just a copy of your supposedly corrupted files, then restoring them will restore the problem. (Also, a backup must always be on a separate drive.)
    – benwiggy
    Sep 15 at 14:05
  • 1
    Shouldn't you replace the software often so that it doesn't go stale and corrupt? My understanding is the writing of a file is orders of magnitude less likely to error than data sitting idle and unchanged. Also - each update runs clean / validate / check scripts - so you're avoiding those pre- and post- checks by avoiding updates.
    – bmike
    Sep 15 at 14:36

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