It’s Time to Upgrade Your OS, Isn’t It?

Apple, Google, and Microsoft are updating iOS, Android, and Windows

Updating OSes

Lifewire / Hilary Allison

I live fearlessly, updating my phone, laptop, and tablet as soon as a new operating system is ready. Sometimes, I don’t wait. Like a parachutist jumping out of the plane without checking his gear, I install the betas. I’m that kind of tech nerd.

Most of you, and for very good reason, are not. I’d wager that when software updates come along, you hit “no thanks,” pushing off the updates until they literally can no longer be avoided, or you decide to throw out the old hardware and buy a new gadget that comes with, you guessed it, the new software.

Weighing the Risks

Upgrade season can be stressful. Apple’s just launched all of its OS updates:

 Microsoft has its Windows 10 November 2019 update.

Google’s Android 10 is just starting to roll out to phones.

On the other side of all these updates stands a nervous populace weighing the risks of upgrading their precious hardware.

Reasons to Upgrade

Major operating system updates are not like bug fixes and performance enhancements. They’re system enemas for your devices, cleaning out the plumbing fully before pouring the new OS back in. It’s why when I see a phone, laptop, or tablet performing poorly—crashing repeatedly, not responding to taps or clicks—I consider taking the leap on that upgrade.

 When my wife complains that her phone or iPad isn’t working, I always ask, “Have you updated lately?” The answer is always a death stare.

 Operating system updates are also major feature enhancements, adding attractive capabilities you didn’t have before. In iOS 13, for example, you have:

On iPad OS, Apple is pushing its core mobile OS to a new, more productive space. iPadOS splits the difference between tablet content consumption and almost laptop-level productivity. There are things, like multiple instance of one app open, that are only available on the iPad if you update to iPad OS. 

Android 10 (a.k.a. "Q") brings:

  • dark theme
  • Multitasking bubbles
  • Much better privacy controls
  • Live, real-time video captioning

Ever since Microsoft re-positioned Windows as a service (it’s still an operating system but is updated in a more rolling service-like fashion) Windows 10 updates haven’t been quite as scary or disruptive. It’s not that each update doesn’t bring meaningful changes, but, if you have the latest version installed, you might not even notice the changes.

On the other hand, 32.8% of all Windows systems still run Windows 7, which points to another major reason why people still hesitate to update.

But first a true story.

Don’t Let This Happen to You

This week, Apple launched MacOS Catalina. I’d seen the update in action earlier this year at Apple’s Worldwide Developers Conference and even test-drove the beta. I was especially excited about Sidecar, which adds second-screen support for newer iPads.

I opened my office-supplied MacBook Air (it’s barely six months old) and started the upgrade process. It went smoothly until the very end when I was asked to log back into the system. The screen had a gorgeous new Catalina-infused background with my name near the top and a box where I could enter the password. I typed it in, and a progress screen appeared. Then the system audibly sighed (I’m not making this up), rebooted and returned to the same log-in screen. I tried to launch the system a half-dozen times to no avail.

Catalina Fail
This did not go as planned.  Lifewwire / Lance Ulanoff

A few hours later, a company memo from our IT department arrived urging all of us to NOT install Catalina on our Macs.

Corporate system and devices are often pre-loaded with system-level software, anti-virus, and VPNs that are usually out-of-step with the latest operating system updates. Cash-strapped companies sometimes wait years to update systems because they do not want to buy new hardware (not my issue), which is why so many are still on Windows 7.

Hubris and Worries

I’m not someone who subscribes to the view that all 1.0 software is bad, but I admit, I should’ve checked in with IT before I installed Catalina.

To be fair, the reasons for not installing Day One updates make some sense. 1.0 software has been proven so dangerous that the public usually doesn’t even get 1.0 software anymore. Apple released iOS 13.1 to the public and very quickly followed with iOS 13.1.2.

Not all aging hardware can handle these updates, though that’s easy-enough to check before you install.

Major OS updates are system enemas for your devices, cleaning out the plumbing fully before pouring the new OS back in.

Changes can be frustrating. Companies like Apple, Microsoft, and Google don’t just improve their operating systems, they move things around. Sometimes features disappear altogether. In the latest App Store, Apple moved the Updates button to make room for “Arcade.” Arcade is cool, but I miss my at-a-glance way to check if there are updates for all of my apps.

Going back is hard, sometimes impossible. Android phones often make doing so especially difficult, unless you’re willing to get technical. If you backed up your iPhone before an iOS update, you can usually restore from that. Windows, I think, does the best job of letting you roll back recent OS updates without too much fuss.

So What

I like progress; for baseline stability and security, having the most up-to-date operating systems across all your devices is usually the best way to go. Still, you need to weigh all the factors before you dive in. Are the new features "must have?" Can your device handle the new update? And does your company support it?

That last bit of advice is something I should’ve taken for myself.

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