Windows 10 has been out for almost 2 years now. If you’re still running Windows 7 or Windows 8.1, is it time for you to upgrade? Maybe.

A little background first. If you’ve been reading this blog or listening to my podcast for the past couple of years or longer, you know that I did not take kindly to Microsoft’s rollout of Windows 10 back in the summer of 2015. They were forcing the “free upgrade” on Windows 7 or 8 users, even if people specifically opted to NOT take it. And many of those that ended up with Windows 10 had all kinds of problems with it. It was a nightmare, and Microsoft lost a lot of credibility with their users because of it. During that first year, I voiced my disgust with Microsoft and Windows 10 loudly and often to my readers and listeners.

As a result, many of those that follow me online are still using Windows 7. And I still get the question sometimes, “Should I upgrade to Windows 10 now? Is it safe?”. This is especially compounded by the fact that my OWN computer now is running Windows 10. But that came about rather unexpectedly. My previous computer died and its replacement happened to be running Windows 10. I didn’t intentionally just do the upgrade.

Should you upgrade now?

If you’re using Windows 7 – you probably don’t need to yet – but there are some disclaimers. Frankly, there’s nothing wrong with Windows 7. It works great. So if your computer is working okay (and the hard drive has been tested and is not showing signs of failure), you can stick with Windows 7 for now. But keep in mind, sometime in the next couple of years, you’ll need to start thinking about either upgrading your computer to Windows 10, or replacing that computer (and the new computer would have Windows 10).

Windows 7 will be supported until January 2020, but you DON’T want to wait until December 2019 to start thinking about this. There’s no big hurry at the moment, but get it done before the rush.

If you’re using Windows 8.1 – you probably should upgrade – but there are some disclaimers here too. This is not because Windows 10 is so great, but rather because Windows 8 or 8.1 is just so awful. It was a goof-up by Microsoft. They screwed up the whole Start button and Start menu, making Windows confusing and difficult to navigate. Of course, if you’re used to using it and it’s no big deal, then don’t worry about upgrading right away. But in my opinion, Windows 10 is working well enough that you would probably like it better than the crummy design of Windows 8.1.

Windows 8.1 will be supported until January 2023 so you’ve got lots of time to make that decision. But for me, I’d much rather be using Windows 10.

And, it’s not like the upgrade is perfect either. Windows 10 still has issues, and not all of them are just bugs in the software – some are built right in to the operating system intentionally by Microsoft. Some of the things I don’t like:

That might seem like a lot of bad features, but in reality most can be reconfigured and avoided, either with a third-party program or by a setting in Windows 10 itself. And these things are nothing compared to the problems I saw when Windows 10 was first introduced – printers stopped working, peripheral items like keyboards, mice and optical drives weren’t compatible, etc. Those things are pretty much taken care of now, unless your printer is really old. You can check your printer’s manufacturer website to make sure it will work with Windows 10.

So the bottom line is this: If you’re using Windows 7 and everything is working fine, you don’t need to upgrade to Windows 10 – yet. If you’re using Windows 8.1, you can upgrade to get a version of Windows that’s easier to use. And if you buy a new PC now, it’s going to come with Windows 10 anyway (including some of those bad “features” I listed), but it can be customized and it’s a lot better than it used to be.