My Windows 8.1 comedy misadventure

On Monday evening, just after 9 o'clock, I decided to finally replace my Windows 7 installation on my main desktop PC with Windows 8.1. I assumed the upgrade process would be relatively straightforward, taking a couple of hours at most and requiring minimal effort on my part other than putting the DVD in the drive and clicking "Next" where necessary. I should add that I had no burning NEED to install Windows 8.1 -- I just fancied a change after all these years, and am one of those people who likes to be running the latest version of any software. I've been running Windows 8.1 on the secondary partition on my MacBook Pro and have had no complaints about it, once Charms and other annoyances have been disabled and Start8 is installed. And besides, Windows 8.x has a nifty file transfer dialogue.

More fool me.


9:30 PM

My problems started when I discovered that, despite Windows 8.1 being a free upgrade available to all Windows 8 owners, I couldn't actually install Windows 8.1 using my Windows 8 license key. That's right, it demands a specific Windows 8.1 key. No problem, I thought -- I'll install Windows 8, then install the Windows 8.1 update afterwards. After all, it's basically just a service pack, right?

More on that later. First, however, a more immediate problem.


10:00 PM

I updated to Windows 8 successfully and found myself with over 100 Windows updates to install... one of which, I assumed, would be the Windows 8.1 update. I promptly elected to install all 100+ updates in one go and sat back to wait for it to do its thing.


10:30 PM

"Failure configuring Windows updates. Reverting changes. Do not turn off your computer".

Oh.

Obviously, the system had decided to crap itself when faced with so many updates at once. No biggie, I thought. I'll wait for it to roll back, then install them in blocks of, oh, say, 20 at a time. Problem solved.

Except not.


00:30 AM

Two hours(ish) later, after several reboots and the same error message continuing to appear, it began to dawn on me that this wasn't going to be plain sailing. Realising that there was nothing for it, I pulled the plug and booted into the recovery menu, intending to make use of the system refresh utility that made its debut with Windows 8.

To explain, you have three options when you do this. The first and least invasive of these is a system restore, which takes you system back to an earlier point in time with a minimum of hassle. This has been a standard feature in Windows for many years now, and I've used it on a few occasions in the past without any problems.

Error message telling me there are no usable system restore points. Strike 1.

The second, more invasive option, is a system refresh, which scrubs all your settings and installed programs but keeps your files intact. Not ideal, but oh well. I decided to try that.

"There was a problem refreshing your PC. No changes were made." Strike 2.

Option three is the nuclear option: what Microsoft calls a reset, which is essentially the equivalent of wiping your entire hard drive and reinstalling from scratch. Microsoft claims this means you'll lose your files, though obviously if, like me, you keep all your files on a secondary hard drive anyway, that's not the case.

"There was a problem resetting your PC. No changes were made." Strike 3.

At this point I realised the whole system was goosed to the point that Windows couldn't even nuke itself, meaning I'd have to do the job for it. By this time, it was approaching...


01:00 AM

Not a problem. I've reinstalled Windows more times and on more computers than I care to remember. It doesn't faze me, and it's not as if there's anything irreplaceable on my C: drive.


01:30 AM

And the process of installing a fresh copy of Windows 8 was straightforward enough. Once I'd got myself into a fresh desktop, I set about downloading the 100+ Windows updates all over again and installing them in chunks.


02:30 AM

Success! Windows was fully updated and ready for action. Only... where was the Windows 8.1 upgrade? There was no download showing up in Windows Update, where you'd logically expect to find it.

A quick visit to Google told me that, contrary to all logic, you do not in fact download the Windows 8.1 update through Windows Update, but rather through the dreaded App Store. OK, then. It was easy enough to find: a big button reading "Update to Windows 8.1 for free." Which I dutifully clicked.

And then got this message:

HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA
HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA
HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA
HAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHAHA.

So that's it? No explanation? Just "Something happened." Great going, Microsoft. Really fantastic job with the error message there.

Back to Google once again, and it turned out I was far from the only person having this problem. It appears to be a widespread issue with multiple possible causes, and nothing I tried, from multiple reboots to deleting the Windows Update cache, could fix it.


03:30 AM

By this time I was, to put it mildly, a little ticked off and having trouble keeping my eyes open. However, faced with the choice of admitting defeat and calling it a night, or staying up and persevering, I chose the latter. During my Google search for solutions to the aforementioned cryptic error message, I'd inadvertently discovered that it's actually possible to install Windows 8.1 without owning a Windows 8.1 key. Microsoft provides generic keys for use by businesses which are installing Windows on multiple machines at once, with a 30-day grace period after that to acquire and input a legitimate key in order to fully activate the installation. And, it turns out, you can activate using your Windows 8 key.

That's right. You can activate Windows 8.1 using a Windows 8 key, but you can't INSTALL Windows 8.1 using a Windows 8 key. Oh, Microsoft.

So I performed a complete reinstall of Windows. AGAIN.


05:00 AM

Seven and a half hours after I started what I thought would be a seamless and fast operating system update, I finally had a working, fully updated copy of Windows 8.1... with none of my programs and settings, of course, but by this time I was grateful just to have a functioning computer. I'll no doubt end up spending much of today reinstalling things, tweaking the OS to my tastes and so on.

So, at the end of the day, I guess the question has to be "Was it worth it for that fancy file transfer dialogue?" I'll leave you to figure that one out. For now, all I'll say is that this was a somewhat different experience to upgrading my MacBook Pro from OS X Mavericks to Yosemite, a process which took all of 25 minutes and required no user input whatsoever beyond restoring the privileges for a couple of tools I've installed to help OS X make more sense to my poor Windows-infused brain (Karabiner and ShiftIt).