I'm still getting used to living in a small town. This time, it's the neighbors. I've lived in much bigger cities where I never even met my neighbors during my entire residence there. Here, the neighbors are more sociable, sometimes bringing cookies or fudge, sometimes complaining about Windows, and sometimes offering tips on my power tool posture when fixing my porch.
It's kind of delightful, in a "How did this happen to me?" kind of way.
In any case, one neighbor came over to say "Hi" when I took Pixel pup outside, and then a guy from down the street who was walking by also decided to meander over for a visit. Neighbor One had asked my plans for the day, and I explained I was about to go in and start testing a review product using a Windows 10 VPN.
That got him started on a rant about Microsoft, Windows, Amazon, Jeff Bezos' peccadillos, the President, whether Tilly is getting too much screen time on Star Trek, and then all the way back to Windows 7. He doesn't want to upgrade to Windows 10.
This comment seemed to light a fire inside Neighbor Two, who resented Windows 10 "being shoved down our throats." That's a direct quote. It turns out that the crux of the objection was, "I like Windows 7, why should I pay to move to Windows 10?"
You (probably) don't have to pay
Because Microsoft did a big push to get folks to upgrade to Windows 10 by July 29, 2016, many people mistakenly believe that the only way to upgrade to Windows 10 now is to pay.
As it turns out, that's not true -- for individuals, anyway. If you have a machine that's compatible, and if you have a valid Windows 7 or Windows 8.1 license key, you can still upgrade to Windows 10 for free. Microsoft just doesn't actively promote that fact.
As with many things Microsoft, the confusion is understandable. On Microsoft's Windows 10 page, it lists the price of Windows 10 at $139, an amount that clearly offended both Neighbor One and Neighbor Two.
I explained to them that if you initiate the update on a currently valid machine and follow these instructions, you can probably do an in-place upgrade to Windows 10 without spending a penny.
That's for individuals. If you're at a larger company, your costs will depend on your Windows contract with Microsoft.
Our conversation continued. Even after I showed that they might be able to upgrade their older Windows 7 machines for free, they had objections. Since they're objections you also might have, I'm sharing them with you here.
"Name one thing that I actually care about that Windows 10 will do for me."
There's one key feature that makes Windows 10 a must-do upgrade: Security. Windows 10 has far better intrinsic security features than Windows 7. This makes sense, because when Microsoft introduced Windows 10, it had six years more experience fighting off cyberattacks than it had when Windows 7 was introduced.
Patches have closed up some Windows 7 weaknesses, but Windows 7 (even patched) is nowhere near as secure. Mainstream support for Windows 7 ended a few years ago. Microsoft will stop issuing free Windows 7 security updates in less than a year.
Some corporate installations can pay (an ever increasing price, actually) for ongoing Windows 7 security updates, but Microsoft is neither making it easy nor cheap -- and it's not available for consumers and small businesses.
I explained that identity theft is a billion-dollar problem and that the cost, time, and stress involved in recovering from identity theft can be overwhelming.
I also shared some of Ed Bott's salient points about the cost to businesses: Recovering from ransomware or regulatory violations as a result of poor security can result in big loses and even bigger fines.
Windows 10 was designed with a much deeper level of security in mind. Windows 10 is very different internally from Windows 7. Windows 10 was developed for the modern computing world, with all the threats and issues we face every day. Windows 10 has a huge number of architectural features that improve security. That's not patches. That's core design.
Clearly, it's time to move to Windows 10. Microsoft built a lot into Windows 10 beyond security. The entire OS was built with a tremendous number of performance improvements, better memory management, and far fewer crashes.
Microsoft catalogs a whole bunch of other Windows 10 benefits, including Cortana, Windows Ink, and even the Edge browser (which they're replacing, so go figure). Microsoft calls it the best Windows ever, which although is as generic a marketing answer as you can get, is actually true. Windows 10 is an exceptional OS.
"But, I don't go to dangerous websites. I'm smarter than that."
My discussion of improved security prompted this objection. But the world has changed and threats are more universal.
Ten years ago or so, it was the case that pretty much only sketchy websites were rife with malware. But that's no longer the case. Fully legitimate websites can be penetrated and attacked with malware.
Some of them quietly download trojans to visitors' machines, to be activated later or just run in the background. Some sites get infected when they run their normal upgrade process and a component of the site, like a plugin, has been infected and that infection is downloaded via the automatic update.
As a user, your personal care about which sites you visit is no longer a reliable protection against malware. You now need to be sure to run a fully patched operating system. Since Windows is the biggest target for malware, and since enemy actors have become intimately familiar with Windows 7's flaws, running it leaves a big, gaping security hole on your computer.
It's bad, very, very bad.
"My machine works perfectly now, if it ain't broke, don't fix it."
If you're running Windows 7, your machine ain't "ain't broke." It's a wide open giant malware-sucking vacuum. You are bound to get p0wn3d. Upgrade.
Beyond that, if you're running a machine designed for Windows 7, it's at least seven years old. That's like 50 years in dog/computer generation years. Every element in a modern PC, from storage to CPU, memory, network, chipset, and graphics have been subject to Moore's law for all those years.
A low to middle-of-the-road 2019 PC that costs $500 will blow the doors off that seven-year-old Windows 7 PC. It well might be worth the cost of the upgrade.
"I know new hardware won't be supported on Windows 7, but I have no intention of adding new hardware. My machine is perfectly fine as it is."
Quite frankly, this was where I was when Windows 10 first came out. I had a number of very carefully tuned, highly optimized machines that, after years of tweaking, finally worked like a dream. I did not want to mess with perfection.
But... they were connected to the internet. I've had to clean up my share of viruses and malware over the years, had to get credit cards reissued after credentials were stolen, and helped others clean up identity theft and ransomware attacks. It's just not pretty.
Also: How to prepare your organization for the end of Windows 7 support TechRepublic
If I could have guaranteed those machines would be permanently air-gapped from the internet, maybe then I could have turned them into museum exhibits of a bygone OS era, but everything I use connects online. So, yes, I upgraded. You need to, too.
"I don't even know if Windows 10 will work on my machine."
This is a legitimate concern. Windows 10 does have some issues with ancient hardware, but so does Windows 7. In the next section, I'll include a bunch of great articles that will walk you through the process of finding out if your machine can support Windows 10.
There is, of course, another option: Getting a new machine. I know that can be costly, but there are actually a number of under-$200 Windows 10 notebooks available on Amazon with modern processors, and even a free year of Office 365.
Also: Windows Update for Business: A hands-on look at how to take control TechProResearch
I'm not including the link to these machines, because they change constantly. If you're looking, go to Amazon, select the Computer section, then Laptops, then Windows 10, and enter between $100 and $200 for your price.
If your current hardware won't support Windows 10, it's bound to be a lot slower than even low-end modern hardware that does. This might be a good time for a cheap, higher-performance upgrade in your gear.
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Upgrading to Windows 10:
Here at ZDNet, we have written extensively on the Windows 10 upgrade process, tips, and lessons learned. Here's a set you might find helpful as you go on your upgrade path.
Microsoft's much-hyped free upgrade offer for Windows 10 ended in 2016, right? Not exactly. If you want to move from Windows 7 to Windows 10 without spending a penny, read Ed Bott's how-to.
Adrian Kingsley-Hughes provides a helpful guide for checking your machine's compatibility
This is Ed's ongoing FAQ about Windows 10 upgrades. It's a good first place to start.
You've got a new PC running Windows 10 Home. You want to upgrade to Windows 10 Pro. Ed shows to get that upgrade for free. All you need is a Pro/Ultimate product key from an older version of Windows.
This is my guide for folks moving all the way from Windows XP to Windows 10. It's also got some good hints even if you're just moving from Windows 7.
It's often easy to blame Microsoft for every flaw and failing in our Windows update experience. The fault, dear reader, may not be in the updates, but in our own installs. This is a must-read by Yours Truly discussing how we diagnosed and found a rather frustrating upgrade problem.
This is my tour of how the upgrade went for 10 very different machines. The TL;DR version: mostly good, with one really rough upgrade.