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Microsoft Loses the Windows 7 Upgrade Battle

Consider Microsoft’s plight. Hundreds of millions of customers, ranging from home users to the enterprise, bypassed Windows Vista and chose to stick with XP. Worse, many of them actually downgraded computers equipped with Vista, because they didn’t want to deal with its problems, real or imagined.

Without having the exact figures on hand, I think I’m safe in saying that the R&D costs spent to create Windows 7 are in the billions of dollars. Microsoft has a huge development staff to feed, and projects routinely take years to complete, even if Vista’s successor is mostly a refresh with some revised eye candy and a new name to counteract the stench of its predecessor.

You would assume, then, that Microsoft’s executives would really want to do everything they can to encourage their user base to dump an eight-year-old operating system and embrace Windows 7. Instead, they have made the upgrade path as draconian as possible. Instead of just putting the DVD in your PC’s drive, you have to first backup all your stuff to an external drive — assuming you have one — because you’re forced to do a clean installation to get the latest and greatest version of Windows.

The setup process will actually erase your PC’s hard drive, meaning that once Windows 7 is up and running, you’ll have to restore all your documents, and each and every application, assuming you even have the installers anymore. It’s very much different from the Mac, where installation files, even if they stretch beyond the Applications folder, are usually easy to find and copy to another drive.

Yes, Microsoft does include a utility to migrate your own files, and there are third party products that promise to simplify the XP to 7 upgrade mess. But there are no guarantees any of this stuff will really work reliably in the real world. No wonder computer shops are going to make a bundle selling you upgrade services.

Or you can just buy a new PC and put that old box out to pasture. While Microsoft doesn’t earn near as much money from each user license if you get Windows 7 preloaded on your new computer, they won’t be peppered with near as many support calls from disgruntled users.

On the other hand, the upgrade from Vista to 7 can, theoretically, be done in place without having to do anything more than sit back, click a few prompts and get on with your business. Well, at least that’s the theory, but the real world doesn’t always match Microsoft’s “head-in-the-sand” expectations. Or maybe they would rather not tell you.

Now consider what I tried to do this week after receiving a copy of Windows 7 Ultimate from Microsoft. You see, my particular installation of Vista Ultimate was done with VMWare Fusion 3.0, the recent major upgrade to their Mac virtualization software. My test Mac, by the way, is an Early 2008 Mac Pro with 16GB of RAM, running 10.6.2.

After the Vista installation was complete, I changed very few system settings beyond screen resolution. I also installed the latest Firefox, Opera and Safari to check how our sites appear on the Windows platform, plus the special bundled version of McAfee’s security suite supplied by VMWare.

So you’d think that a straight in place upgrade ought to proceed without difficulty. Well it would on any Mac even after far more system and application changes, but Microsoft is nothing if not inscrutable about such matters. What this means is that my Windows 7 installation was interrupted several times to warn me of potential compatibility issues.

What compatibility issues? Well, after closing the Windows 7 installation, I discovered a prompt from, believe it or not, Apple, to install QuickTime and Safari upgrades. Once that was done, I started the 7 installer again, only to be admonished to restart my PC to complete the installation of some unknown updates before trying Windows 7 again. After three failures, the installation actually began in earnest.

I won’t bother describing the process in detail. Except for somewhat prettier status screens, it’s not terribly different visually from Vista. Every process is frequently interrupted with “Please Wait…” prompts. I also ran into a few “Gathering additional information before expanding files” that were just as peculiar. Just what information does Microsoft need on a system that’s only a few steps from stock?

There were also several restarts during the process plus a notice that “Setup is upgrading registry settings” that had the usual frightening implications. Indeed, the dreaded Registry is one of the “features” that persists in Windows, despite being an endless source of performance bottlenecks, instability and general customer confusion. You’d think that Microsoft could manage to set aside a few billion dollars to just get rid of it and devise a settings database scheme that actually works.

In all fairness, I suppose some of the peculiarities might be attributed to running Windows in a virtualized environment rather than the real thing. On the other hand, neither VMWare nor Parallels ever presented problems installing Windows XP or Vista, so maybe it is a 7 thing after all, or just the consequence of upgrading an existing Vista setup rather than creating a new virtual machine.

At the end of the process, which consumed well over 90 minutes after the initial interruptions, Windows 7 restarted as a nearly virgin system. As you know, it doesn’t even include such basics as contact, calendar and even email software until you actually download and install the Windows Live Essentials files from Microsoft’s site. Talk about dumb!

While it’s too early to say much about Windows 7, I do agree with the critics that it’s noticeably snappier than Vista, with a more attractive interface. That doesn’t necessarily make it easier to use, and while I suppose it is more Mac-like, it doesn’t come close to replacing Apple’s operating system.