The Heroic Saga of Upgrading to Windows 8, Guest-Starring: Microsoft Live Support!

By Commenter Jack Butterworth on at

Six days, 22 hours and 9 minutes later, I've finally managed to install Windows 8. I don't know what I did to upset the god of Windows Vista. Maybe he'd thrown a tantrum at getting fired on his birthday. Maybe somehow he knew I was going to write this column. Maybe there just Is No God of Windows Vista (that kinda figures actually.) All I can tell you is that it took me a week to get from Vista to 8.

I nearly couldn't buy it in the first place -- I'm in Colombia, South America at the moment, and it wouldn't let me pay with VISA, or AMEX, or Paypal -- it turns out Microsoft South America will only accept payment in the heads of rival operating system bosses. Or possibly dollars. Because it's impossible to change money into another currency, right?

I eventually got my Dad (bless him) to download it in the UK and send me the link. It came, in a blaze of purple and white glory, and I set it running. Then it crashed. So I set it running again. And it crashed again. No error code, no report, no information why, apart from a giant unhappy emoticon which appeared on the blue screen of death and made me feel a lot better, definitely.

(Actually, there was some text which appeared on the blue screen of death, but I will remain forever in the dark as to what it said, as it appeared for about a gazillionth of a second, and unlike the average Microsoft user, I don't possess the ability to freeze time. I even went through the whole installation process again, just to try and read the text, and say hello to the unhappy emoticon again of course, who was still really helping.)

With no options left, I was forced to turn to Microsoft Live Help. Enter Sheryl G; her winning smile, and her dubious command of English. She took control of my machine, and four hours later, she signed off, having achieved nothing. Yes, four hours. Four. Enough time to watch two films. Or listen to four albums. Or two and a half tracks, if you're a Pink Floyd fan.

During our time together, she tried updating Windows, and when that didn't work, started looking through the online help pages to see what might be wrong (reassuring, I know). She tried uninstalling all my anti-virus software, while I cringed as she saw Peggle Deluxe under my installed programs. She installed a Fixit utility, while (I hope) cringing as much as I had. She disappeared for a fag break for over an hour, while I discussed with a friend whether she was just hanging around forever to try and seduce me. We slowly invented an elaborate story of how she was desperately in love with me, and had just disappeared for an hour to pluck up the courage to ask me out. We discussed where she sat on the hotness scale, and what she was into in the bedroom. We quietly hoped she hadn't turned the webcam on.

She eventually came back; fiddled with my registry, then left, but not without this touching email:

You can smell the sexual tension.

So I tried again the following day, with Vanryn, who burst into my life with a name like an extra from Game of Thrones and a profile picture like Oddjob. Just like Oddjob, in fact, he was a man of few words. He demanded control. He took control. He took one look around. Decided that I should install Windows from an external flash drive. I did. It didn't work.

I was getting annoyed, so I wrote to Microsoft in my politest, Britishest tone, and copied it to Bill Gates and Steve Ballmer, just because.

Three days later, I got this (this time from Cheryl with a C): 

Boy, that escalated quickly. I mean, that really got out of hand fast.

And then, a day later, this:

DAMN! You got me, Microsoft. Beaten. Out-thought. Snookered. I actually sent you the angry email because the problem was FIXED! I thought it would be fun. A valuable use of my time. I just wanted to try and hook up with one of your operatives again. Of course Vanryn was right. The installation HAD worked. It was just Windows 8 looked exactly the same as Vista and was just as shit. (I'm only two days in, reserving actual judgement on this for now.) Wait.

In fairness to MSFT, the guy who eventually fixed it was a bit of a boss. He took one look at a long text file with lots of numbers in it that detailed about everything my computer had ever done (you can tell my technical knowledge has run out here, right?) He changed the DNS server and I was away; it worked fine. The fact that I was on the phone to him the whole time he was looking was the only awkwardness. I thought of asking him whether he knew Sheryl to break the ice, but decided against.

I don't really know what to think of the service in general. On the one hand, they did spend seven hours of their time trying to fix the thing, which is very committed (by the last operative, if we assume the US minimum wage per hour, they were actually losing money on the sale.) Then again, it did take me a week to upgrade to Windows 8. I'll give them a very hesitant thumbs up. Windows 8 doesn't look too bad either. Though Peggle Deluxe better still work.

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