Three days after Microsoft releases Windows 10 to the general public on July 29, I am making a special trip to my Mom’s house to personally upgrade her Windows 8.1 laptop.



I can’t wait, and neither can she. After spending years learning how to get stuff like online banking and email done in Windows XP and Windows 7, she’s been completely flummoxed by the radical changes in Windows 8.1, which removed that familiar Start menu and replaced it with a Start screen.

David Pogue called it “TileWorld” and pretty neatly summarized why my Mom’s not the only one who’s been confused by her Windows PC over the past couple years.

So consider Windows 10 Microsoft’s apology, and listen for the word “familiar,” in the video ads that you’ll see over and over for the next few months. Given the enormous marketing budget Microsoft has put together, you will hear a lot about it unless you check into a monastery at the top of a mountain.

On my week-long road trip, I’ll be visiting a lot of friends and family, and I fully expect to be peppered with questions about Windows 10, with “Should I upgrade?” at the top of the list. Here’s what I’ll be answering.

Here’s what you need to know to decide whether to upgrade.

1. Yes, it’s really a big deal. And yes, it’s really free.

Windows 10 is the next major release of Microsoft Windows. It is also, in a sense, the last major release of Windows, because with Windows 10 you’ll get updates and upgrades automatically, for free, for as long as that device is alive.

And those updates will be free, in an offer that’s good for a full year after that July 29 launch date, on your existing PC, unless you’re one of the few holdouts still clinging to Windows Vista or XP. You already get a deal like that with your smartphone, your web browser, and (ahem) your Mac. Apple stopped charging for upgrades a few years ago. Now your PC is joining the always-up-to-date crowd.

If you are running Windows 7 with Service Pack 1 or Windows 8.1, you’ve probably already seen the Get Windows Now notifications, which began popping up last month. Reserve your copy now, and the new version will download automatically sometime after July 29.

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I’ve checked the fine print carefully: There’s no catch, no secret gotcha. This is not a trial version, and you won’t get a bill next year or the year after that.

2. It has a Start menu.

No one knows just how big the I Hate Windows 8 Club is, but I suspect that the guy who developed the most popular Start menu replacement program for Windows 8 probably has two Teslas and might even have earned enough for a private jet by now.

So the mere fact that Windows 10 has a Start menu might be enough to win you back to Windows, or at least convince you to try the upgrade on your PC.

If you do, you’ll make TileWorld vanish. Well, almost. When you first start Windows 10, you’ll find yourself at the familiar (there’s that word again) desktop, where you can click the Start button and find all your old programs, plus a few new ones.

Yes, those tiles on the right side of the Start menu are an awful lot like those on the (shudder) Windows 8 Start screen, complete with live headlines that refresh as your day goes on. But you can make them smaller, or add your own, or completely ignore them and just use icons on your desktop and your taskbar, because on a regular PC that familiar desktop is where you start. If you really, really want the Windows 8-style Start screen, there are options you can dig through to enable it.

3. The upgrade is pretty easy, and you can roll back if you don’t like it.

Microsoft has been running its Windows Insider program since last fall, with a few million people using early editions of Windows 10. Over the 10 months or so since the first preview edition was released, they’ve gotten a lot of feedback from those Insiders—bug reports, feature requests, demands.

They’ve also had millions and millions of opportunities to test the upgrading process. (I’ve been personally responsible for a few dozen upgrades on test PCs.) The upgrade process is pretty fast, if you don’t count the time it takes to download the 3 GB or so in the Windows 10 installer. In general, you can expect it to take an hour, more or less, depending on your hardware. I’d suggest letting this part of the upgrade run overnight.

And if you try it for a few weeks and decide, “Nope, I liked my old PC better,” you can roll back to your old operating system. No kidding.

4. Yes, your old software will still work. Well, most of it, anyway.

Despite the new look and some new stuff under the hood, the parts of Windows that run your old familiar programs aren’t that different. When you sign up for the upgrade, you get a report that lists any programs or devices that might have trouble after the installation is complete. (You’ll probably have to get the latest version of your antivirus program, for example.)

I have run across a few very old programs that don’t work properly, but 99% of what I use daily runs just fine on Windows 10. And yes, that even includes familiar programs like Google Chrome and Apple’s iTunes. (Although you should at least check out Microsoft’s new Edge browser, which gets rid of everything you hated about Internet Explorer, and the Groove Music service, which gives Apple Music and Spotify a run for their money.)

5. Cortana is very, very cool.

Don’t tell Cupertino, but Cortana is basically Siri’s younger, smarter sister*, with a bit of Google Now tossed in. The “intelligent personal assistant” is built into every copy of Windows 10, and she’s capable of answering questions, booking appointments, setting alarms and reminders, keeping track of stocks and news headlines and upcoming travel, filling you in on sports scores, and much, much more.

You set up Cortana for the first time by going through a quick interview. After that, you can fine-tune her responses any time by reviewing and editing those entries in her notebook.

You can type your requests to Cortana if you’re using a standard PC, but she* is perfectly capable of understanding the spoken word if your laptop’s microphone is of sufficient quality. And, of course, you can ask Cortana to tell you a joke, which invariably results in a groaner like: “What do you call a dog who does magic tricks? A labracadabrador.”

*Cortana is unmistakably female, with many prerecorded responses voiced by Jen Taylor, who also provided the voice of the original Cortana character in the video game Halo.

And last but not least…

6. You can take your time about it.

You don’t have to decide right away. It’s never a bad idea to watch and wait.

Windows 10 is a work in progress. Although it’s likely to work just fine for many people on Day 1, it’s also likely to have its share of annoying bugs and features that don’t exactly work as expected. Many of those issues will be fixed over the next few months and delivered through Windows Update. Waiting means you get to watch other people struggle with those early issues while you wait for them to be ironed out.

Now, if you’ll excuse me, I’ve got to get packing for that road trip. “Hey Cortana, how’s the traffic on I-5 South right now?”

Ed Bott is the Obi-wan of Windows experts, with the same grey beard and calm demeanor. He’s currently celebrating the 20th anniversary of his first book by working on book #27. Not surprisingly, it’s called Windows 10 Inside Out. You can find out what Ed’s up to lately by following @edbott on Twitter.



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