Apple’s latest Mac update, macOS Catalina, was released earlier this week, and with it came a flurry of complications both minor and major.

For one, this update is the first for Apple to drop 32-bit application support, which is causing all sorts of headaches for users of smaller apps, plug-ins, and other software that may not be updated for quite some time or may have been created by a company that no longer exists. There are also a fair number of other issues with Catalina, like Adobe software incompatibility problems and unforeseen hurdles related to the removal of iTunes.

That leads us to a series of important questions for Mac users who may be at risk of having important workflows disrupted by Catalina. What exactly might go wrong if you do upgrade? Should you upgrade now, and what should you do before pulling the trigger? Or should you hold off for now, and if so, what’s the best way to do that and also monitor when it might be safe to make the jump?

Apple first announced that it would ultimately wind down support for 32-bit apps more than a year and a half ago, when it began pushing alerts to macOS High Sierra users that 32-bit software was “unsupported.” The apps still worked, but with Catalina’s official unveiling back in June at WWDC, Apple made the eventual discontinuation official. With the launch of Catalina, 32-bit apps no longer function.

That has resulted in some understandably messy problems. For instance, legacy versions of Adobe products like Photoshop use some 32-bit licensing components and installers, meaning they won’t work after you upgrade. Not even Adobe’s uninstaller will work post-Catalina upgrade because that, too, is a 32-bit component.

Adobe recommends you not update your Mac if you rely on this older, pre-Creative Cloud version of Photoshop or Lightroom. It also says that, even if you do upgrade, you should probably uninstall that software first or else it will be difficult to get rid of once its rendered inoperable.

Other popular pieces of software ensnared by this 32- to 64-bit transition include older versions of Microsoft Office, numerous legacy versions of Mac apps like GarageBand, and discontinued apps like iPhoto. For those who do play games on a Mac, it’s likely quite a few are 32-bit and there’s no way to salvage them after upgrading to Catalina.

Over at The Tape Drive, Apple blogger Steve Moser has compiled a list of 235 apps and counting that aren’t supported in Catalina. That includes some versions of Transmit, 1Password, QuickBooks, VMWare Fusion, and Parallels.

But the issues extend beyond the loss 32-bit app support. Due to incompatibility issues, even newer versions of Photoshop installed and managed using Creative Cloud are having file naming issues, plug-in verification problems, and video rendering hiccups. Adobe says on its support page for the issue that droplets, ExtendScript Toolkit, and Lens Profile Creator will flat-out fail to run.

Because Catalina marks the official end of iTunes as a standalone app, third-party apps that relied on iTunes as a repository for music files and for the features it offered for linking with other software are also running into issues. This has mainly affected DJ apps like Rekordbox and Traktor that offer the ability to sync XML files generated from iTunes, which breaks that link between the software and DJs’ music libraries, a feature crucial for live performances. For those who depend on that software, Apple is telling them not to upgrade to Catalina, either.

There are bound to be more issues that pop up as more users upgrade to Catalina and run into new, unforeseen issues. But for now, if any of the above mentioned pieces of software are vital to your job or your daily computer use, it’s likely a good idea to hold off on upgrading.

Should you upgrade now?
If you do want to upgrade, there are some easy ways to figure out if your machine will be hit hard by the loss of 32-bit support. Apple has gone out of its way to ensure that when you do choose to install the new OS, you’ll be made aware of the software installed on your machine that won’t be supported post-update.

But if you want to do that ahead of time, before downloading Catalina and getting to the final stages of the install process, you can use Spotlight search on your Mac to open the System Information tool. From there, scroll down to “Software” and click on “Legacy Software.” At the top of the window you’ll find all the software that will become inoperable once Catalina is installed. On my work machine, it was only one app - an old piece of software for recording Skype calls. But on my home machine, a years-old Mac mini, I have loads of legacy software.

I have an old version of Microsoft Office on that machine, a 32-bit version of Valve’s Steam launcher I never uninstalled, and what appears to be old versions of iMovie and pre-Creative Cloud Adobe apps. I’m using my Creative Cloud subscription on this machine, so I can uninstall that Adobe software. But had I not heeded Adobe’s warning to do so pre-Catalina, the company says I would have had to resort to using its manual cleanup tool, which can be annoying to troubleshoot and time-consuming to perform.

The question of whether you should upgrade largely rests on whether you’re okay taking the risk that some apps might no longer function or you might run into issues you were unaware of even in supported 64-bit software.

If you’re like me, you don’t use highly specialized apps and you’re not using a four- or five-year-old Mac. You mostly use your newish laptop or desktop for web browsing, general productivity stuff (calendar, notes, file management, etc.), light media creation, and editing and writing. In that scenario, upgrading to Catalina is reasonable and likely won’t cause you too much trouble.

Why you might want to hold off
There are plenty of reasons not to upgrade to Catalina. Apple says the OS will run on computers from as far back as 2012, but that, of course, means you may have tons of 32-bit software lying around that you use from time to time without realizing it.

Forgoing those apps just to use Catalina is, in my option, not worth it when the upgrades you’re getting are mostly centered on new devices. For instance, you can’t use the new Sidecar mirroring feature without a Skylake Mac and a newer iPad.

Another reason why you may want to hold off on upgrading is if you’re a creative professional, someone who uses Photoshop or any of the above mentioned music software affected by the iTunes removal. It’s always safer to work on a machine that’s integrated into your existing workflow, instead of risking breaking something and hitting a roadblock on a project that has a due date.

As The Verge’s Dieter Bohn argues in an article aptly titled, “You don’t need to update your operating system right away,” consumers, and especially Apple fans, have been lulled into a sense of complacency over software updates because of how stable the mobile variety have typically been. He calls it a low-risk, high-reward decision to update a new app or move to the latest version of iOS because, while you might run into a bug here or there, you do get access to cool new features, nice wallpapers, and generally speedy third-party app adoption of new capabilities.

The same is not true for the Mac, which as a much more open platform, can involve more complications, and carries a higher risk in the event of a serious bug or incompatibility issue. “You probably depend on your Mac or PC for ‘real work,’ and so updating on day one could threaten that real work - literally threaten your livelihood,” Bohn writes. “It’s better to wait and see how things shake out, to let other people experience the problems and report them.”

In the event you do end up holding out, there is one thing you’ll want to do: head over to Settings, click Software Update, and uncheck the box for “Automatically keep my Mac up to date.” That will ensure that your Mac doesn’t try to sneakily install the update on your behalf. Most Mac users have this box checked by default, so you’ll have to manually turn off the setting to avoid a forced Catalina install.