Everyone in the Windows world is sitting on a bit of a time bomb: On July 29, Windows 10 upgrades cease to be free. Let's be clear. While some of you die-hards might not want to move off of Windows XP, that OS is no longer safe to run on the internet. So, unless you intend to keep your machine offline, it's worth considering an upgrade.
For many of you, particularly those with older machines running older versions of Windows, if you haven't upgraded yet, you're probably not going to pay for an upgrade later. So that gives you just about two weeks to get it together and do the upgrade now, while it's still free.
For those running Windows 7 or Windows 8, the upgrade is straightforward. Heck, it's impossible to ignore. Microsoft has gone out of its way to make upgrading to Windows 10 easy. Some might call it nagging, but let's not quibble.
In my case, I had a few machines sitting in my garage that still had Windows XP on them (and one with, I kid you not, Vista). There were a few reasons I decided to do the upgrades. First, of course, I write about this stuff. But I often press old machines into service for some project or another.
Then, there's the good-deed side of things. I sometimes bump into people in my community who desperately need a computer. If I can hand-me-down something that's growing weeds in my garage, but would be a true help to someone else, why not? That said, while I don't mind giving someone an old, slow machine, I will not give them an unsafe one. That means moving to Windows 10.
Another reason is that newer versions of Windows have been able to breathe new life into these old machines. Both Windows 8 and Windows 10 run on old hardware really nicely. In fact, some folks have reported that newer OS versions actually increase the performance of those old machines.
Before you start to gather the materials and supplies you'll need to do the upgrade, you should make sure your machine can actually run Windows 10.
Here's a helpful guide on what you'll need to do, including links to the Microsoft compatibility checker. The key, I found, was to make sure you have at least 1GB of RAM for a 32-bit upgrade or 2GB for a 64-bit upgrade.
Getting started, what you'll need
So, let's get started. Here are some of the things you'll probably need to make the jump.
A thumb drive with at least 4GB of space. I recently bought a 16GB thumb drive from Amazon for about $5, and most of us have some spare USB sticks laying around.
An unused, sacrificial Windows 7 or Windows 8 license code. This could be the sticking point for some of you. You're actually going to be upgrading to Windows 7 or Windows 8, and then to Windows 10. To get the free Windows 10 upgrade, you need to sacrifice a Windows 7 or Windows 8 license.
Many of us have a bunch of licenses left over from machines we've taken out of service, so dig around. I purchased a bunch of cheap Windows 8 licenses, so I had a few I could pull from. But this is important: Your XP or Vista license won't do it. You need an actual code from 7 or 8.
If you have a Windows 8 license, I'd recommend starting with that instead of Windows 7. You'll actually be upgrading to Windows 8.1. I found that a bit less fussy than upgrading to Windows 10 from Windows 7.
A spare, modern computer. You could just do the whole process on the machine you're upgrading, but, as I said above, I don't recommend going online with Windows XP. So, to download files and set up the thumb drive, a working, modern machine will help.
A DVD burner and blank DVD (optional). If you don't want to go the thumb drive approach, you can burn your Windows image to DVD. I won't be discussing this, because I've done my absolute best to forget DVDs ever existed. But you have that option.
A Netflix subscription (optional). This process takes time. I found that re-watching old Top Gear episodes made the time pass more pleasantly. But then again, I use re-watching old Top Gear episodes the way some people use Xanax, so, you know...
An old machine running Windows XP (or Vista, I guess). This point is probably obvious, but for the sake of completionism, I'm including it.
Fast track to Windows 10 upgrade
Update: Ed Bott tells me there's a better way than what I described (and did myself) below. Back in November, he wrote about how you could do a clean Windows 10 install using Windows 7 or 8 license keys. At the time he wrote that, you had to be opted into the Windows 10 insider channel, but he tells me it's now available to everyone.
To make this work, you'll need to head over to Microsoft's Windows 10 Disk Image (ISO) page and download the ISO. If you're using a helpful, modern machine (anything Windows 7 and above), you can simply right click on the ISO and burn the image to a DVD.
Since I promised that I was avoiding DVDs entirely, here's Adrian's guide to creating a bootable thumb drive from an ISO.
Safely remove the drive from your main computer, insert it in the XP machine, reboot. Then keep an eagle eye on the boot screen, because you'll want to hit the magic key that will drop you into the machine's BIOS. Once you're in the BIOS, make sure you boot off the USB stick.
Go ahead and install Windows 10. If everything works, you can skip the rest of this article. If the process doesn't pan out, here's the longer process using an intermediate OS to take you the distance.
Preparing for the first upgrade
This is going to be your first step. I know, it seems like a pain to first upgrade to an earlier version of Windows, and it is. But, if you have a bunch of Top Gear reruns to watch, it's not really that bad. You do a few clicks, and go back to fast cars. Rinse, wash, and repeat.
I went through the Windows 8 upgrade process in some detail in this article: 8 lessons learned from upgrading a dog-slow Windows XP machine to Windows 8.
Key among the lessons learned was making sure Windows XP was updated to SP3 before doing anything else. If you're running an old Windows XP install and need to get it up to SP3, it might take a few more reboots.
Now, switch over to your modern Windows machine, plug in the USB stick, and point your browser to Microsoft's Create Installation Media page. This is how you get good install images for Windows 7 or Windows 8.
Click in, then choose Windows 7 or Windows 8.1 at the bottom of the page, and follow the directions.
Here's an important tip. Don't try to install 64-bit Windows 7 or Windows 8 if you are running 32-bit Windows XP. Everything will fail if you do. Be sure to match bitness. In most cases, you're probably upgrading Windows XP 32-bit, which means you'll need the 32-bit version of Windows 7 or Windows 8.
Note that if you have a Windows 8 (rather than Windows 8.1) license key, you're fine. Download the Windows 8.1 installation, then enter your license key, and Bob's your uncle.
Run the media creator and send that install to your thumb drive. Make sure you don't mind torching that drive, because the media creator will zero it out to create a bootable image.
Finish up, and then properly unmount the drive. You'll move it to your old Windows XP machine next.
Installing Windows 7 or 8
Before you shut down your old Windows XP machine, make sure you back up anything you care about. You're going to be nuking the drive. Okay, now shut down.
Plug in the USB stick and turn on the computer. Keep an eagle eye on the boot screen, because you'll want to hit the magic key that will drop you into the machine's BIOS. Once you're in the BIOS, make sure you boot off the USB stick.
I found that one of my machines had both hard drive priority and boot priority, and I had to set both to get the USB stick to boot, so you might want to keep that in mind.
Go ahead and normally install Windows. There are the usual cornucopia of options, and I'm guessing you know enough about Windows installs to get those options correct. If you're unsure, Ed Bott has a helpful list of Eight things to do right away after you set up Windows 8.
One thing you can avoid doing is updating Windows 7 or Windows 8. This will save a lot of time and a lot of reboots. Because you're going straight to Windows 10, you (probably) won't need to run intermediate updates.
I say probably because I had no problem on one machine, but on one Windows 7 machine, I had to take it all the way through the update cycle before Windows 10 would properly install.
Once you're able to boot into your intermediate, but reasonably modern Windows, it's time for the next step.
Installing Windows 10
Let's get one thing out of the way. Even if you can't make it all the way to Windows 10, you've just completed a massive upgrade to your machine - and made it safe to use online. But, if you've done the compatibility check phase I recommended earlier, you should be just a few hours away from running brand new Windows 10 on your old box.
Here's something I discovered. I found that going to Microsoft's site and doing the web-initiated update failed on me with some regularity. Instead, I directly downloaded the Windows 10 download tool from Microsoft and ran it on the target machine.
I just let these tools download to my Downloads folder and then executed them. From that point on, I mostly found things to be smooth sailing, especially from Windows 8.
There you go. How many reboots did you have to get from Windows XP to Windows 10? Let me know in the comments below.
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