Windows 10: A tale of 10 upgrades

If you're still unsure about upgrading to Windows 10, you have two weeks to do so for free. David Gewirtz leads a tour of how the upgrade went for 10 very different machines. The TL;DR version: mostly good, with one really rough upgrade.
Written by David Gewirtz, Senior Contributing Editor

We're about two weeks away from July 29, when Windows 10 upgrades will no longer be free. After a few months of on-again, off-again work, I've finished upgrading my stable of computers. I thought you might enjoy a walking tour of the upgrades -- the good, the bad, and the ugly.


Some of the machines I upgraded to Windows 10.

Quite obviously, my stable of machines is going to be different from yours. But you might find it instructive to see how the upgrade process went across a relatively wide range of machines, capabilities, and configurations.

I inventoried all the Windows machines here at Camp David. We have a total of 15 that are known to boot. In addition, I have three dead machines that I've kept around either to repair someday or salvage for project parts.

If you add in all the Macs, the tablets, the dedicated file servers, the random single board computers, and the occasional robot, the only conclusion possible is that we have way too many computers for just two adults and a puppy. Sigh.

The first thing we did was decide which machines to upgrade or leave with their existing Windows versions. Of the 15, we decided to upgrade 10 of them, and we left five alone. The three dead machines were also left untouched.

With that in mind, let's dive in.

The 10 Windows 10 upgrades

All told, nine of the upgrades went quite smoothly. One was a royal pain. I'll run you through the list in the order I did the upgrades.

Sager 9150 laptop - In 2012, this was the most high-performance laptop I could find, with dual SSDs, dual high-performance graphics systems, 32GB of RAM, and the fastest Intel mobile CPU available.

This was my first upgrade to Windows 10 from Windows 7, and I ran into a bunch of problems that I eventually attributed to an application I forgot was running on the machine. Unfortunately, the in-place Windows upgrade sparked a ton of reliability problems with games. I'm going to do a fresh install when I get a chance, making sure I pay particular attention to video driver updates.

Parallels VM running Windows 8 - The first of a series of virtual machine upgrades, my main Windows 8 VM, went quickly and with no hassles at all.

Parallels VM running Windows 8 with 1GB - The upgrade on this test VM failed initially, with a warning that I didn't have enough memory. The VM was running 64-bit Windows on a 1GB VM. When I reconfigured the VM to run 2GB, the Windows 10 upgrade proceeded smoothly.

Parallels VM running Windows 8, also with 1GB - Since I'd experienced the need to reconfigure the previous VM to 2GB, I did that first with this one. The upgrade was reasonably quick and painless.

Parallels VM running Windows 7 - This is my primary teaching machine, which I use to test and grade student programming assignments. It has a Visual Studio install.

This upgrade initially failed, providing me with the following error message: "Windows 10 will not run on this PC due to an issue with Parallels Display Adapter (WDDM)." Because I had already successfully updated three Windows 8 VMs running on the same Parallels VM foundation, I knew the problem couldn't really be a problem with the underlying virtual hardware.

After a little digging, I found a knowledge base article on the Parallels website with some guidance. The article advised making sure Windows 7 was fully updated before attempting the upgrade. I'd already done that. The article also advised downloading the Windows 10 Media Creation tool from Microsoft, which I discussed last week in my migration steps article.

I've noticed in the past that Windows 7 seems to like upgrading using a version of Windows 10 installed on a USB stick, rather than just installing directly from the Microsoft website. In any case, once I ran the installer off the USB stick, the upgrade to Windows 10 ran smoothly. Visual Studio has been rock solid and fast on Windows 10.

Asus Eee Box - This is an old 1.66GHz Atom processor-based machine from 2010 that I used to run as a dedicated-purpose server monitor. With 1GB of RAM and a 5400RPM drive, we're not talking speed demon. It was still running Windows XP.

Having not been smart enough to follow Ed Bott's advice, as I discussed in my updated article last week, I first upgraded this machine to Windows 8. I was required to provide an unused Windows 8 upgrade license code. Once I finally convinced the Asus to boot off the USB stick, the process went smoothly.

I then did a fresh install of Windows 10, which also went smoothly. Later on, I learned I could have installed Windows 10 directly using the Windows 8 license code. That tidbit of information saved some time on subsequent upgrades.

Two Zotac MAG PCs - I also have two 2010-vintage Zotac MAG boxes -- each running Intel Atom N330, Nvidia Ion, and 2GB DDR2 RAM, along with slow 5400RPM drives from back in the day. These had already been updated to Windows 8 sometime in the past. The Windows 10 upgrades were successful and without incident.

Dell netbook (who we call Della) - Della did not want to upgrade. In fact, it took me four days to get Della to upgrade from Windows 7 to Windows 10. This was not fun.

Della was a $492 purchase in 2009, with all of 1GB of RAM, a 1024x600 display, and an Atom N270 1.6GHz processor. But what makes Della so special was my wife's cherished Passion Purple color scheme. Over the years, we updated Della twice, opening her up about four years back to add another gigabyte of RAM, and then about two years ago, to put in an SSD.

When I sat down to update Della to Windows 10, she was already running Windows 7, which was an upgrade from the original Windows XP Della shipped with.

I twice tried updating Della from the Microsoft website, which had been a relatively successful practice, at least with the Zotacs. Della hung both times.

The first time, she got all the way through the Windows 10 upgrade circle and stopped at 76 percent. The second time, she stopped at 96 percent. Della is slow, so this took a full day.

Next, I tried using the Windows Migration Tool from a USB stick. This also failed at 76 percent. There was clearly something Windows 10 didn't like sometime through the install process.

I decided to boot off the USB, and do a custom install. I chose to not delete the existing partitions, and to keep our old files. After chugging for a while, Windows 10 generated an error saying it could not reinitialize the deployment engine. I did some research and determined that this error tends to come up when there's an issue with partitioning, or with the disk. Since we'd replaced the drive a year or so ago with a random aftermarket SSD, I figured that was the problem.

The next time, I booted off the USB and deleted the OS partition, keeping the protected partition. I got the same error.

Windows 1.0 to 10: The changing face of Microsoft's landmark OS

In my penultimate attempt to get Windows 10 on this machine, I deleted all the partitions. This time the installation completed, but it wouldn't activate. Because all the partitions were gone, Windows 10 did not recognize that this was an upgrade. As a result, I had to sacrifice one of my fresh Windows 8 keys.

But there was a problem. I'd installed Windows 10 Home on the machine and all my Windows 8 keys are for Windows 8 Pro. Windows responded with "You are running Windows 10 Home. The Product key you entered cannot be used to activate this edition. (Error code: 0xC004F210)".

Sigh. I did it again. I booted off the USB stick, installed Windows 10 Pro, and completed the installation, this time with a successful activation.

For those keeping track, it took seven tries to update Della, and that included sacrificing one paid-for Windows 8 key, because the upgrade process lost the Windows 7 license that was already installed on that machine (no, for some reason, I don't have that old license key written down).

It took four full days to get this install to work, going back and forth to check on the machine every hour or so throughout the days. Fortunately, Della was the only real problem we had.

ZDNet's resident Windows 10 guru Ed Bott informs me that I did one install too many. Rather than reinstalling to go to the Pro version, I could have used a special license key that enables version switching. Ed has a very helpful FAQ that might save you some time.

Samsung Series 9 Ultrabook - Our Samsung Series 9 Ultrabook was purchased in 2012, and other than a fan failure and a battery failure, it has served us well. It's fast, running 8GB RAM and an i7 processor on it's very slim 15-inch screen. After the hassles involved with getting Della updated, updating this machine was a breeze.

The five that remained legacy

Now that you've seen how the Windows 10 upgrades went, I'll run you down the list of the five that didn't get upgraded. They are all towers:

My old main desktop, a Vista machine I haven't booted for at least five years - It uses a ton of power. It's loud, and at some point, I'll just strip it and scrap it.


Four of the five towers in storage.

Two early media tanks - One still runs Windows XP, and the other runs Windows 8 with a pooled-storage array. Both use relatively obscure hardware to get so many drives into the cabinet. A Windows upgrade could break the very delicate system that works now, and since they stay powered off and exist simply as an ancillary backup of older media, there's no reason to take a chance on an upgrade.

A four-disk CD ripper - This is also based on Windows XP. We used this as our rip-monster to be able to digitize all our CDs. It doesn't have a network card, so there's no risk with putting it online. It, too, uses a very custom configuration. If we ever needed to batch rip more CDs, we have a system that can do it. We still have the actual CDs in storage.

A cassette tape digitizer - This thing was fussy even when we built it, but we finally were able to make it work. It was primarily used to rip some of my wife's very valuable recorded performances and vintage mix tapes. Since this machine is super-custom, totally special-purpose, and entirely unlikely to work after an upgrade, we left it as-is.

And there you go. That's my Windows inventory. All told, the Windows 10 upgrade went relatively smoothly. Even if you have a bunch of machines, you still have time to do your upgrades, as long as you start now.

You can follow my day-to-day project updates on social media. Be sure to follow me on Twitter at @DavidGewirtz, on Facebook at Facebook.com/DavidGewirtz, on Instagram at Instagram.com/DavidGewirtz, and on YouTube at YouTube.com/DavidGewirtzTV.

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