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When Is the Right Time to Upgrade Your Operating System?

By Bradley Chambers in · End Users · October 6, 2016

In the good-ole days, we saw significant operating systems updates every 18 to 24 months. In today’s world of “what have you done for me lately?” it is much faster, with Apple, Microsoft, and Google undergoing major updates to their operating systems at least once a year.

A question I often get after these updates are released is: “Should I upgrade to version __ since it just came out?” My response is always: Eventually, you’ll have to upgrade because there will be a new-device purchase, or an application you want to use will require it.

Here are the things you should consider when facing an iOS, Windows, Android, or macOS upgrade.

1. Hardware Dependencies

Will any of my existing external hardware break? This includes printers, scanners, IoT hardware (watches, fitness gear, etc), custom display applications. Before upgrading, be sure to check the manufacturer’s websites for information on compatibility and potential bugs. As an example, the ScanSnap scanners have a significant flaw with macOS Sierra. You can read more about it on their website

2. Software Dependencies

As with hardware, check with each vendor of your key software. If your CRM application doesn’t support the new operating system, then upgrading will shut your work down. If your key Outlook or Mail.app plugins don’t work on the new OS, then your workflows will be impacted. While many of the major OS upgrades have private and public betas, all software vendors don’t take part in them. It’s important to do your research ahead of time.

3. What Benefit Is There?

As with any major upgrade, there is a learning curve. With macOS Sierra, it was a pretty minor interface upgrade. With Windows 8/10, Windows 7 users were pretty confused, though. Before upgrading, look at the feature list. Is there a compelling reason for you to upgrade in the early days of a major release? One thing to consider is that you are often going from the most stable version of the current OS to the least stable version of the newest one. Is there a key impact to your workflows to warrant any potential early bugs?

4. Security Vulnerabilities

On another angle, security is often a benefit of new OS upgrades. If a new zero-day vulnerability is discovered for your OS, will the manufacturer patch older versions of the OS or simply patch the newest one? If you are in Corporate IT, be sure to pay attention to information from your resellers and other vendors. If you aren’t in IT, be on the lookout for security bulletins from your IT department. In the latter situation, you won’t likely initiate the upgrade, but be aware that there may be a security-related reason for a forced upgrade (which may affect some of your hardware and software needs).

There is often a lot of excitement around a new version of iOS, Windows, Android, and macOS. As the excitement dies down, a lot of little bugs are uncovered. Take your time, and do your homework before you press the upgrade button. Even if most of the upgrades are free, there is still the chance your workflows will be impacted, or bugs will slow you down.

One last thing, be sure to backup your data before you begin the update process.

Bradley Chambers (@bradleychambers )

Bradley Chambers has been the Director of Information Technology at Brainerd Baptist School since 2009. At BBS, he manages a network of Apple and Chrome OS devices. He also writes at Tools & Toys and The Sweet Setup.