If you’ve decided that you want to upgrade to macOS Ventura next month, either when it’s released or soon afterwards, now is the time to start planning and preparing for that. This article makes some suggestions to help.

Upgrading to a new version of macOS is always unpredictable. Some of the biggest leaps in the past, to High Sierra with APFS, or Catalina with its boot disk restructuring and loss of 32-bit, have been smooth and trouble-free, while others you’d have expected to be straightforward have been near-disasters. Always expect the unexpected, and plan to deal with catastrophe, then you can only be pleased when, a couple of hours later, Ventura is running sweetly.

Perhaps the overriding need is sufficient time. Never try to upgrade when you only have a short window to complete it in. If you’re pushed for time, even minor glitches will throw you and could leave your Mac unusable until you can make enough time to sort it out.

Where is your Mac coming from?

If your Mac is already running macOS Monterey 12.6, then upgrading to Ventura should, with a bit of care and luck, be only like installing a rather large update, at the end of which you have lots of new features to explore. Don’t bank on that, of course, but, fingers crossed, Ventura shouldn’t prove a pig.

Differences between Big Sur and Monterey are rather greater, although both share the same disk structures, so deep internal surgery shouldn’t be required, particularly if you’ve been keeping up with its security updates.

Catalina may prove tougher, though. Your Mac’s startup disk may be structured similarly to those of Big Sur and later, but a great deal else has changed. Careful planning and an escape route are more important to you, as they are to Macs making the even bigger leap from Mojave or earlier. If you haven’t yet freed your Mac of 32-bit history, then I recommend you read my earlier articles about upgrading from Mojave.

What is your Mac?

With three main streams of Mac now, you’re likely to see bigger differences between those types.

Most straightforward should be Apple silicon models, particular if they’re running at the default Full Security level. If you have had to reduce that to load kernel extensions, then I wish you the best of luck, as you’re in largely uncharted territory. System extensions shouldn’t be a problem, though, as they run in userland, so shouldn’t be able to compromise successful boot.

Intel Macs without a T2 chip should also be relatively straightforward, particularly if they’re coming from 12.6. But those with a T2 chip could present rare but more serious problems: there’s always the chance, if anything goes wrong with the T2’s iBridge firmware update, of ending up in a boot loop. Every time my iMac Pro plays dead during an update my palms still start to sweat. Maybe if your Mac has a T2 you should also prepare your lucky rabbit’s foot or rosary just in case. It is a good idea to have another Mac with the latest version of Configurator 2 installed and a suitable cable in case you need a back-to-back resuscitation, if you feel up to that. This may seem unduly pessimistic, but if you prepare for the worst you shouldn’t be disappointed when it all goes fine.

Is it clean or custom?

Over the years we all collect software and peripherals that maybe push macOS a bit far. The more that has accumulated on your Mac, the greater the chances pf problems when upgrading. If your Mac requires kernel extensions or drivers to support peripherals, then you’ll need to be confident that both the software and hardware remain fully supported in Ventura, and that neither will be so broken that you can’t use that device, or your Mac can’t achieve stability.

Although Finder and other customisations aren’t as radical and should be much less likely to render your Mac unusable, you will need to check their compatibility to see whether you should remove them before upgrading.

Upgrading essentials

Draw up a checklist of all the things you need to do before you agree to Software Update’s invitation to upgrade. In the days or weeks to go, revisit that checklist as often as you can, both to keep track of what you have completed and to add items you had forgotten. Here are some essentials that need to be covered:

• Key apps. Ensure these are at least up to date, and preferably that you’re running a version known or expected to work well with Ventura.
• Keeping the old. Could you dual-boot between Venture and your previous macOS, or run the old version in a Virtual Machine?
• Which Mac first? If you have more than one Mac, will you upgrade your production Mac last?
• Ample time. I’ll say it again: ensure you have time for a tricky upgrade and more to spare if you need to sort important problems out afterwards.
• Recovery. What if the upgrade just isn’t going to work on that Mac? Can you downgrade it to where it was?
• Fallback or escape route. What do you do if something goes badly wrong and you’re without that Mac for a few days?
• Backups. I like to have two independent backups of everything that needs to go across in the upgrade, one immediately beforehand, and the other fairly recent. Check those backups work before use.
• Key information. Ensure you have a written record of essential information that could need to be refreshed, such as Wi-Fi passwords, Apple ID password, router logins.
• Power. Ensure notebook batteries are well-charged, and your UPS is providing good protection during the upgrade.

I’m sure you’ll have other suggestions to add to those.