Every one of the half-dozen Windows 8 machines I've upgraded to Windows 10 has transitioned smoothly. One even did it by itself while I was traveling. So I have been pretty impressed by the upgrade process, and have said so. But each time we write about Windows 10, the comment threads feature lots of horror stories from readers attempting to upgrade all the way from Windows 7, which is something Microsoft really wants to have happen. So, being a full-service journalist, I decided to bite the bullet and upgrade my work-a-day desktop from Windows 7 -- the machine I read my email on daily, and have kept my financials and personal records on since the day I built it five years ago.
It is exactly the sort of machine that deserves to live on with a new OS: 6-core AMD CPU, lots of RAM, an SSD for booting, dual monitors, and more. What better test of the upgrade process? So, after making a full backup, I plunged in -- and my experience here couldn't have been more different from my experience upgrading from Windows 8.
First, I checked and found not all of my applications were compatible. In particular, I needed to upgrade my PGP software. No small thing, since PGP was bought by Symantec years ago. Nothing wrong with that, but a reminder that, unlike machines that were updated in the last year or two to Windows 8, most machines that have been sedately running Windows 7 for many years are more likely to have old software that needs updating -- and more likely to have software that is no longer supported.
Once I had the PGP issue sorted, I optimistically began the upgrade. There are two pretty compelling reasons for Windows 7 users to want to do an upgrade in place instead of a clean install. The first is that you have to do it that way at least once to get your free upgrade. The second is you've probably got quite a number of old applications on your machine by now, and it wouldn't be a small task to track them all down and re-install them again. That said, an upgrade is almost always going to be more troublesome than a clean install.
Unfortunately, as I've written about before, Microsoft has not fixed any of the horrible parts of Windows Update -- and that goes for the Windows 10 Upgrade process as well. The error messages are still completely inscrutable. I used to curse the long hex codes that Windows Update spewed out, until I experienced several errors this time with no code at all -- only a Vonnegut-esque "Something Happened" in the error dialog. After receiving one of these errors, the familiar rabbit hole of debugging starts: running the troubleshooter, renaming system folders based on vague tips from the web, unplugging devices, re-trying everything, updating the BIOS, changing BIOS settings, and so on.
At no point in this process was there any truly useful information provided by clicking on any error links or provided officially by Microsoft that dealt with the issues. In fact, so many of the error codes have been re-used, or are generic, that looking one up often resulted in tips for installing Quicken or Office, instead of Windows. This is the part I don't understand. Why hasn't Microsoft -- if it really wants customers to move forward -- provided the kind of support information they need? I can't imagine any "normal user" being patient enough to fight through the arcane techniques for hunting down update logs, and the voodoo necessary to try and set things right.
So, after nearly a day of this (a day in the life of the machine, since each step took time, probably an hour or three of my time), I finally got the upgrade to run. Yay! Now I was sure I was on my way. Windows 10 went through its happy dance, and encouraged me to log in. Except I couldn't. For some reason my Microsoft wireless keyboard & mouse weren't being recognized. I needed to remote desktop into the system to work on it. Even sticking an old-fashioned USB keyboard and mouse on the machine didn't seem to help. I'm nearly certain there is some type of funky interaction with my system's motherboard.
I don't envy Microsoft the task of making new code run on over a billion old machines. But that's what Windows 10 needs to do if it really will be the OS that gets customers to move off of Windows 7.
After fiddling around, I noticed that the machine would alternate each boot. Half of the reboots were super-quick, but with no mouse or keyboard support, and the other half took over ten minutes, but the mouse and keyboard worked. That brings me to the next insane thing Microsoft has done that will drive Windows 7 users crazy: Any semblance of communication about whether the system is making progress or merely stuck while booting is replaced with an endlessly spinning set of little balls. There is no way to tell if you are seconds away from a running system, or destined to spend the next day getting dizzy or wanting to take up juggling. In the latter case it is just a question of man versus machine -- as eventually you feel like you either need to punch the screen or hit the reset button.
Windows 10: The pot of gold at the end of the rainbow
At some point during this cycle of fixes and reboots, I realized that when Windows 10 was running, it was a great replacement for Windows 7. Sure, I'd upgraded a bunch of ugly Metro-based Windows 8 machines, so of course Windows 10 was better than Windows 8, but I was expecting Windows 10 to seem somehow foreign on my beloved Windows 7 desktop. It wasn't. The Start menu is still pretty wonky, but it's mostly harmless. The Taskbar works at least as well as it did before, and adds some new features. All my desktop icons were happily in their places. My gadgets were gone, but a quick download of 8GadgetPack fixed that quickly.
The upgrade process unfortunately disabled most of my third-party startup services -- such as my non-stop backup and spam filters. Fortunately, adding them back to startup (Using Run->shell:startup and adding shortcuts) fixed the problem.Life in the fast lane: Becoming an insider
By this point, as happy as I was with the system while it was running, the crazy reboot issues were still driving me a bit nuts. As an eternal optimist, I was hopeful that Microsoft might be well on its way to fixing this type of issue as part of the run-up to its expected large November update (code named Threshold 2). So, I rolled the dice and registered the machine to get Insider builds, and on the "Fast" ring, of course (why not?). After a couple checks, that got me Build 10547 (which I'm running on several other machines already). Sure enough, after the update installed, my machine booted quickly, and happily-recognized my keyboard and mouse. Huzzah!
The progress in these interim builds is an encouraging sign. Hopefully, it means Microsoft will be able to deal with the issues in a more-polished manner for its big November update. In the meantime, if you want to try to make the jump from a healthy Windows 7 install to Windows 10 in its current form -- and have hardware that is more than a couple years old -- make sure to have good backups, and be prepared to spend some time wrestling with drivers, software upgrades, and possibly even replacing some older devices. Otherwise, waiting until Microsoft rolls out its Threshold 2 update (which would have been called SP1 in the old days) is likely your best course of action.
