Why I haven't upgraded my Hackintosh to Catalina yet

macOS Catalina has been released a few weeks ago, as many of you know. I wanted to write a short note on this release for those wanting to see how to apply my recommended way to keeping your Hackintosh up-to-date applies to OS upgrades.

As you may have seen come by on Twitter (consider following me if you haven't already, I post smaller updates and tidbits more frequently over there), I am holding off on upgrading my main Hackintosh machine to Catalina. This is not specifically due to Catalina, but in part it is, too. Let me explain.

My recommendation for when to upgrade

Don't upgrade to the first version of a new OS release on your primary machine(s), hard stop. Whether this is a Hackintosh, real Mac or Windows machine, you're bound to run into issues either caused by the new OS version being buggy, some of the software you're relying on not being updated for it yet, or a sudden hardware incompatibility. As a general rule, try to keep your curiosity at bay in favor of keeping your main machine operational.

In the case of Catalina, you may even want to wait a bit more than just one point update, as Apple's update cycle has been uncharacteristically aggressive. It might take a little more time before the dust has settled and enough bugs and regressions have been patched out.

Now if you have more than one machine, and if you're very curious or just can't wait to start using a certain new feature that comes with the new OS version, you can totally upgrade that machine. I upgraded my MacBook 12", and fortunately have had no issues with it yet. This is also because I am not using many apps on it, and certainly don't game on it, so I had zero 32-bit applications for example.

I rely quite heavily on Docker for my projects so that makes them inherently portable. Since using Docker on macOS means you're running a virtual machine in the background anyway, there fortunately were no issues there, either.

Sounds like it's working great, then why still not upgrade my Hack?

Because of the aforementioned points; hardware differences, unforseen software issues, and what I usually use my MacBook for is not a good enough indication of all the software I rely on working fine on Catalina. Perhaps they all work, probably they do, but I don't want to lose a day debugging or reinstalling things just because I was a bit too excited to upgrade.

This also brings me to another, perhaps more important question.

Why do you want to upgrade?

Put curiosity aside for a moment, and review the actual benefits for upgrading. Obviously long-term sticking with an increasingly outdated version of an OS is likely not a wise choice, but especially initially, the new OS version will in many or most cases be less reliable than the now-old version you are running. There is a clear benefit to sticking with what works, at least until some or most of the kinks have been worked out in the new version.

Specifically in the case of Catalina, and depending on what you use your machine for, this might be a challenging upgrade. The loss of 32-bit application support might affect you if you (occasionally) play games, or if you're a DJ for example. The newness of the OS might make commonly used professional applications made by companies with a known track record of reliability and stability issues and have a general tendency to prefer adding new features as supposed to cleaning up their existing codebase (I'm looking at you, Adobe. Case-sensitivity is a thing, it's almost 2020, get with the times.). If you're relying on Adobe products it's certainly in your best interest to follow a slower upgrade cycle — and consider supporting developers making alternatives, like Pixelmator.

When should you upgrade?

I personally try to avoid upgrading to major new versions until the first point update. The only time I made an exception to that was when new releases were very stable from the get-go; these were usually the upgrades that focussed almost soley on stability improvements as supposed to feature additions. Snow Leopard and High Sierra, for example. But even there, you might want to err on the side of caution, and at least give it a few weeks before you consider upgrading.

What next?

I will upgrade my main machine to Catalina a little while later. And when I do, I'm planning to document the process and create an addendum to my Keeping your Hackintosh Up-to-date article. I am not sure yet when exactly this will happen as I have been busy working on finishing the private beta phase of my project, but I will get around to it sooner or later.

I might also take this opportunity to take a look at OpenCore. My plan for 2020 is to (finally) buy new hardware and build a new machine, but even before that it might be interesting to experiment with that. I have also been pondering over how to handle my needs for both Linux and macOS. A Linux host with macOS virtual machine seems like an interesting approach, but I need more time to research this and see if it truly fits my needs and will work reliably. Right now I'm kind of clunkily dealing with virtual machines and Docker toolbox on my Hack which works for basic stuff, but not for heavier containers like the ones I am developing for my project.

Whatever route I decide to take, I'll be sure to document and share my discoveries (positive and negative alike) here, in case anyone else is in a similar boat.

And as always, thank you for reading.

Have a great day!