WWDC25 is coming – should you upgrade to the newest software?

Each year, Apple releases updates to its core operating platforms. Next week, as part of WWDC25, we’ll get our first look at new versions of macOS, iOS, iPadOS, tvOS, visionOS, and watchOS. All will get the same version number, 26, with some very significant changes to the look and feel of the applications expected.

Along with the changes to the look of these platforms, there will be under-the-covers changes as well. In some cases, applications we’ve come to rely on will either stop working as expected or need to be updated or upgraded. Such is the life of all computer users. At some point, the hardware and software you rely on fall out of support.

So, when is the best time to upgrade your software?

Whenever I have this conversation with someone, the response I hear from people who don’t want to keep software regularly updated is that the combination of hardware, operating system, and applications they have is working reliably and they don’t want to risk making their system less stable. This makes great sense, but there are some issues to consider.

Let’s talk security

At some point, the maker of that operating system will stop providing security updates. In today’s world, where cybercrime runs rampant, keeping a system secure is critical. Today’s cybercriminals don’t rely on viruses. Their goal is to steal data and make money. 

They do this in a few main ways.

1 – Ransomware: Criminals trick people into clicking a link or installing a malicious app that encrypts all your data and then ask for money, usually in the form of untraceable cryptocurrency, to unencrypt your data. 

2 – They log in: Stolen or guessed credentials are a common attack tool used by criminals. Once a criminal logs into a service you use, they use that access to steal from you or impersonate you. 

3 – Vulnerable software: Software is made by humans, and people make mistakes. That can lead to vulnerabilities in software that are exploited by criminals. And the time between vulnerability being disclosed can be just hours. 

The first issue can be addressed by using endpoint security software. We used to call this anti-virus, but it is more sophisticated these days. 

The second issue can be minimised by using a password manager (Apple’s Keychain or Passwords app do a great job of this) so you can generate and use unique, complex passwords for every different service you use. And, wherever possible, use either multi-factor authentication (where you enter a second code to log in) or a passkey. 

Vulnerable software is remedied, to a large extent, by keeping your software up to date. Apple releases security updates for all its platforms regularly. But, eventually, older software is longer supported. As a general rule, Apple offers updates for about five to eight years after a new platform is released, with newer software versions typically updated faster than old ones.

Big changes can be hard

There’s an old fable about a lumberjack and their favourite axe. That axe had the head and handle changed many times over the years. But it remained the lumberjack’s favourite axe. Of course, after so many changes, it was no longer the original axe, but the changes happened incrementally, so they were easier for the lumberjack to adapt to. 

The same goes with software. Apple’s annual changes are usually quite subtle, but over a few years, they accumulate. I have a 2010 MacBook Air that still works. But when I try to use it, the differences in the software to what I’m using today are massive. 

Staying up to date, or close to it, ensures that when changes are made, they won’t be as jarring.

Legacy software

It’s a sad fact, but eventually, software developers abandon apps. Sometimes, this is a commercial decision not to continue developing an app, or the developer has moved on and neglected to keep the application working. Over the years, popular software like the Eudora email client or Bento by FileMaker have ceased to be maintained or released. 

In other cases, developers make the decision to only support a limited number of operating system versions. Typically, this might be the most recent release and two or three previous releases. If you don’t keep your operating system up to date, you may find you can’t update if you don’t upgrade a few apps along the way. 

There will likely be financial and operational costs with this. Not only will you need a paid upgrade, but you may have to upgrade files or learn new features and functions. But these costs are likely to be incremental if you stick with supported software.

Should you upgrade to Apple’s latest releases?

I don’t think you need to upgrade to the latest versions of any of Apple’s platforms on the first day they are released. But I do think being more than one or two versions behind can be risky.

Waiting any longer means you won’t get the latest system security updates as fast as possible, you may find your software is no longer compatible, and you miss out on the benefits that come with newer software.

I tend to upgrade my software quickly so I can get used to the changes as quickly as possible and find any unsupported or broken apps quickly. 

For most people, I suggest not being more than one operating system release behind.

But if you have a legacy app or peripheral that won’t work on newer software, I suggest isolating that to a Mac that does not have an internet connection. You can do that either with an older Mac you keep or through virtualisation software.