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Windows 7 upgrade problems

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Today, I attempted to upgrade Vista ultimate to Windows 7. What a disaster. When will I ever learn?

It all sounds so convenient: “simply” pop the Windows 7 disk into the DVD, follow the wizards to upgrade windows to the latest version.

At this point, I should mention that I am incredibly lazy when it comes to installing the latest operating system and perhaps my experience with Windows over the last 17 years hasn’t helped my reluctance to upgrade.

Installing operating systems and software is a time consuming, non productive activity in my opinion. To install an operating system from scratch and load the software that I need to run my business can easily take a day or more. This is a day that could be spent designing, coding or marketing my software and services.

Upgrading an operating system sounds like the most time efficient way of doing this thankless but sometimes necessary task. A successful upgrade can take just minutes compared to a full installation that can take hours or even days. Therefore, I tend to always give the upgrade option a shot.

My latest experience with Windows 7 upgrading Vista is one of complete failure. Windows 7 hit a BSOD fault at around 80% installation progress and decided to automagically revert me to Vista. On the plus side, I suppose at least I was left with a working operating system.

Now I’m left with having to do yet another full installation from scratch if I want Windows 7. I could well do without the day or so downtime so will probably end up sticking with Vista until such time as I’m forced to build a Windows 7 system from scratch.

The interesting thing for me is in reflecting on my experience with attempting upgrades with various Windows systems over the last 17 years. Here’s a summary:

  • Windows 3.1 to Windows 95 – failed
  • Windows 95 to Windows 98 – failed
  • Windows 98 to Windows ME – failed
  • Windows ME to Windows XP – failed
  • Windows XP to Windows Vista – I don’t even know if this was possible and went for a fresh install
  • Windows Vista to Windows Visa SP1 – failed big time with continuous boot BSOD. The worrying thing here was SP1 came over on auto-update. One day my PC works and the next it’s a pile of useless junk thanks to auto update that runs on someone else’s schedule.
  • Vista Ultimate 64 to Windows 7 64 Ultimate – failed.

Wow! This is quite a record when looking at it written down. Had I have looked at this earlier today, I wouldn’t have even bothered trying the upgrade route.

What conclusions can be drawn from my experience then?

Well, either I am just plain unlucky or perhaps it may be the case that Windows upgrades just simply don’t work in most real world situations.

I realize that, from a technical perspective, operating system upgrades are incredibly complex in having to deal with the endless variations in hardware and software on any single PC. However, I cannot beleive that anywhere a majority of Microsoft customers experience a successful experience with upgrading Windows.

With my cynical hat on, I would suggest that there is very little tangible value in the facility to upgrade to latest versions of Windows. For me, it hasn’t worked for the last 17 years. I’m always optimistic but the reality is that the upgrade functionality simply does not work for what I suspect to be most people for most of the time.

The best thing from a customer perspective would be for Microsoft not even to provide it’s consistently disappointing upgrade features. At least this way, thousand of collective wasted hours could be saved from abortive upgrade attempts. Is this likely? I suspect not. Providing “easy” upgrade paths is a fundamental sales hook.

Ultimately, I would sum up Windows upgrades like this:

  • It just doesn’t work for most people in most cases.
  • Don’t believe the marketing hype.
  • Backup your data, wipe the system hard drive and go for a fresh install.
  • Upgrade might sound like a time saver but by the time you’ve grappled with multiple failures, you burn more valuable time.
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