早 The Price of Upgrading to Catalina

So, time to upgrade toCatalina or is it?

I usually get excited about the yearly Apple update cycle, but this year has left me cautious. Lets look at why you might want to hold off on hitting the upgrade button.

Looks like a harmless upgrade, doesnt it?

Safari 13 Extensions

Safari 13 is a nice update to the stock web browser. But, Apple have completely reworked how Safari extensions integrate, putting an onus on app developers to rewrite them and distribute them via the App store. Extensions which havent been updated will cease to function following the upgrade.

Unfortunately, you may have already been impacted by this, as older versions of macOS will attempt to install Safari 13 during the regular system update process. This means you may have already been upgraded without realising the impact.

One such app I rely on a lot is the excellent1Password. Ive been on an older version for a few years, but the changes in Safari 13 forced the developers to rewrite their browser extension from the ground up. Thats a lot of work, and understandably theyre asking for a paid upgrade of their product to get the new extension.

Of course, not all developers have the time and money to rebuild their extensions from scratch, so chances are some people will have to go looking for alternatives to the extensions theyve relied on for years.

The Reminders App

One of the biggest changes to iOS 13 and macOS Catalina is a reworked Reminders app. Part of the process requires an upgrade to the back-end data, which youll already have been prompted to do on iOS 13 (although on Catalina, I believe you dont have the option to keep using the older data format).

This can leave you in a position where iCloud syncing breaks in Reminders between different versions. If youre someone whos highly dependant on macOS / iOS Reminders syncing, youll need to be careful here until all your devices are on iOS 13, iPad OS 13 and Catalina.

Dont press that button!

32-bit Applications

The most impactful change is seeing support for 32-bit applications become fully deprecated. To be fair on Apple, theyve been warning us about this for at least the last two iterations of macOS. Developers have been given a reasonable amount of time to update their applications to the modern 64-bit standard.

To give you an idea of the kind of apps which can be affected, here are some of my personal bugbears (spoiler:Mostof them are old apps).


Some of my favourite games and game managers will no longer function under Catalina. One example isBoxerwhich allows me to play DOS games.

Another favourite of mine is a game calledEscape Velocity Override. Mac owners of yore will know this series of games well, but sadly the creators are long-gone and the chances of seeing a 64-bit update to this game and games like it stands at 0%.

If youre a Steam gamer, you may see warnings for the Steam client, but fear not; Just manually re-download the app fromtheir websiteto get the full 64-bit experience.

Citrix Receiver

This is somewhat of a niche app to say the least, although you may have heard of it. Its an enterprise desktop virtualisation solution (sounds as boring as it is), and I use the desktop client in my job to access customer live environments.

The issue we have is the desktop client is provided by our customer, and sothey have to upgrade the server side of their architecture to allow me to use a newer Citrix Receiver version. Until then, I simply cant upgrade to Catalina or else the app wouldnt run and I wouldnt be able to do part of my job.


This classic Linux vector art tool is perfect for people like me who dont need to invest in a professional product like Illustrator, and dont mind the clunky Linux-derived interface. Unfortunately, this one wont survive an upgrade.

How Can I Tell Which Apps are 32-bit?

Although prior versions of macOS should have been warning you when launching 32-bit apps, there are a couple of ways to check which of your apps wont be Catalina compatible.

The simplest tool to check which of your appswontrun on Catalina isGo64.

Problematic apps

The other way is touse the System Report featurebaked into macOS.

Running Older Apps under Catalina with Virtualisation

If youre stuck with 32-bit apps you need to keep using, and for whatever reason youve no choice but to upgrade to Catalina, then your only play is to create a virtualised environment to run these older apps in.

If youre not familiar with the idea of Virtual Machines, theyre really cool and allow you to create a sandboxed environment running an older version of macOS within which you can run your older apps.

There are three main players in the Mac Virtualisation market these days, which are:

Since I have no experience with VMWare, Ill just cover VirtualBox and Parallels here.


The de-facto standard for cheap virtualisation, VirtualBox is fantastic for running Windows on a Mac, or a Linux server on a Mac.

Unfortunately, where it falls down severely is with any kind of Mac virtualisation. The reason for this is there arent any VirtualBox Mac drivers available, presumably because Apple doesnt want people running macOS on other platforms.

Building a working Mac VM under VirtualBox is incredibly difficult, although people have already done the hard work for you if you leverage tools such as Vagrant topull down a pre-generated image. But even then, the experience is pretty dreadful.

On my MacBook Air, the VM would crash my entire machine. On my more powerful MacBook Pro at work, its just about good enough to debug things in Safari, but I certainly wouldnt feel comfortable doing any kind of work on it, and playing games would be out of the question.

Sadly, VirtualBox isnt a valid solution here.


This is hands-down the best solution for running older apps. Parallels seamlessly integrates with your Mac, even to the point of running unobtrusively in the background and showing apps as if they were natively running in the main OS.

As with all virtualisation software, the main issues are it eats up disk space and impacts performance and battery life. This is obviously going to be more of a problem for users like myself who have a humble MacBook Air with limited disk space.

The other problem is its not free. Even if you have an older version, you might well need to pay for the latest incarnation in order to run it on Catalina. This is a nice sedge-way into the next section where we talk about paid upgrades.

So, out of some of the 32-bit apps you have, there may be newer versions you can upgrade to. But when you add up the costs, it doesnt come cheap. If you add Parallels into the equation to manage the 32-bit apps which dont have any upgrades available at all, youre talking about spending even more.

An example of such an app my wife relies on isAntidote. Used widely in academia especially in the Francophone world it helps with the notoriously difficult French grammar and punctuation rules needed in academic writing.

And weve already talked about 1Password and other Safari extensions which require paid upgrades.

For a developer to upgrade their app to be compatible with Catalina is a time consuming, and its perfectly reasonable that app creators should expect their effort to be compensated appropriately. Often, these paid upgrades also include new features as well so we shouldnt direct any of our frustration towards the people and companies that build the great apps weve come to rely on.

Do I ReallyNeedto Upgrade to Catalina?

Anyone with the misfortune to follow me on Twitter will have seen far too many ranty iOS 13 tweets from in my feed of late. Apple seem to have hadquality control issueswith their big 2019 OS upgrades. However, whilst on iOS you have to upgrade to the latest version, the silver lining for Mac users is that macOS doesnt force you to upgrade until youre truly ready.

Unless youre lusting after some of Catalinas killer new features, such as Sidecar (which I admit is pretty cool), theres probably not much of a reason to rush to Catalina right away. Apple always provides at least a couple of years of support for versions of macOS, so you can still stick with Mojave for another 2 years and rely on security updates and patches coming down the line.

Writing this article helped me reach a conclusion on what I plan to do with my little dilemma, which is to stick with Mojave for the time being and slowly pay to upgrade the apps I need over a period of time, beginning with the ones impacted already by the Safari upgrade. By this point, I hope Apple will have also ironed out the worst of the bugs weve been hearing about.