Upgrading a user to Windows Vista from Windows 2000

If you're like me, you prefer to install your operating system upgrades on a clean and formatted hard drive instead of simply upgrading from the current operating system. It provides a much cleaner and stable install, and it gives the opportunity to later install only the programs you want, eliminating a lot of the junk that seems to accumulate along the way. Well, what happened to those good ol' days when you could upgrade your current operating system onto that clean (or brand new) hard drive, simply by being prompted to provide the CD from a qualifying product during the installation process? With a Windows Vista upgrade from Windows 2000, that's apparently a thing of the past.

I proceeded with my first Windows Vista installation just like I've done with past versions. I'd copy the user's documents and other necessary local files onto a networked drive, and then format the hard drive either before or during the installation process, or in many cases, simply start with a brand new hard drive. And with this particular upgrade (from W2K), installing larger hard drives might be more the rule for some people than the exception. This Vista upgrade started normal enough, booting from the DVD with the installation program asking for the Windows Product Key. After entering the key, however, I received a message stating, To use the product key you entered, start the installation from your existing version of Windows. What the heck is this all about, I wondered?

Oh well, I wanted to get the first one installed, so I simply decided to forgo the drive format and install from my existing version of Windows. So from Windows 2000, I inserted the Vista DVD and ran the setup program. A screen appeared that apparently gave the option of an upgrade or a clean install, just like I wanted; however, the upgrade option was not available. The Windows prompt said, Upgrade has been disabled. The upgrade cannot be started. To upgrade, you must be running Windows XP with Service Pack 2 (SP2), or Windows Vista. Again, I thought this was rather strange. Windows 2000 is a qualifying upgrade product, so why was the upgrade disabled? Even considering the different architecture used in Vista, it seems to me that Microsoft could have figured out a way to get it to upgrade.

I did have that option of a clean install, however. That's what I wanted in the first place, it seemed I only had to get there a bit differently. So I made my one and only available choice of a clean install, but ran into a couple if glitches. First of all, downloading the installation updates was highly recommended, but Vista couldn't connect to the Web - even if I opened a Web connection myself. The second thing was that I still did not have a drive format or partition option. Nonetheless, I went ahead and installed, pretty much without a hitch.

But I still wanted to install all my upgrades on either a freshly formatted drive or a new one, so did I have any other options? I did, and I could describe several different scenarios (and I think I experimented with all of them), but the key to installing Vista Upgrade from Windows 2000 is the product key, or perhaps, in this case, the lack of one, and when Windows Vista can be activated. Basically, here are the installation options for a Vista upgrade from Windows 2000:

•1. Install the upgrade from your current Windows 2000 installation using the product key: If you choose this option, you cannot format the hard drive, your current program and data files will not be transferred (but rather will have to be reinstalled), and Vista will create a folder called Windows.old for all your old files, although Windows 2000 cannot be run from that location. (If you choose this option, I'd still backup those data files.) With this option, you can activate windows as soon as you establish an Internet connection. (Since this isn't a true upgrade, all your configuration settings will be lost.) •2. Install on a new or freshly formatted hard drive (my preferred method): Boot from the Vista DVD, and do not enter the product key when prompted to do so; and say no, you really don't want to enter it, when asked to confirm. You can both partition the drive (delete and/or add), and/or you can format the drive. The installation will go fine, but when you try to activate the software by entering your product key after the installation, you'll be denied. For this option, when you try to activate the software, you'll be told, The Software Licensing Service determined that this specific product key can only be used for upgrading, not for a clean install. At this point, all you'll have to do is install Vista again, but this time you'll be upgrading to Vista from Vista. That sounds strange, I know, but it's true. When you install Vista a second time, you'll want to do it from the new installation of Vista, not by booting from the DVD. You do want to enter the product key the second time around, and you do want to choose the upgrade option. •3. Upgrade to Windows XP first: You could, I suppose, upgrade Windows 2000 to Windows XP, and then upgrade your XP to Vista. But if most current W2K people are like me, they simply skipped XP all together, which is why they decided to upgrade to Vista in the first place. Besides, it would be much cleaner installing Vista over Vista than over XP, or at least it seems so.

Now that you have your Vista Upgrade installed and activated (or in my case, close to twenty of them), and you begin to weed through all the glitches and idiosyncrasies, you'll still long for those good ol' days, but the ones when you were running Windows 2000 Professional without a hitch and loving every minute of it. And I won't even try to understand how Microsoft engineered a product that told me during various stages of different upgrade attempts, that upgrade has been disabled AND the product I purchased must be installed as an upgrade. I'm still scratching my head over that one.