My Windows Upgrade Battle

Warning: This is a long-winded article recounting my battle to replace Windows Me with a copy of Windows XP on my wife’s desktop computer. As such, it’ll probably only interest those who are facing a similar upgrade war.

A few years ago, I was having problems with my Windows 98 desktop machine. It was a Pentium III 450 Mhtz machine, and it would crash at the drop of a hat, even when doing simple tasks, like trying to surf the web while checking e-mail. When Windows Me came out, I quickly upgraded, without waiting six months (as I normally do).

Years later, I now realize that this was folly; as bad as Windows 98 2nd Edition could be, Windows Me was much, much worse. Yet wiping out the OS and starting over again was a time consuming task, and one that I was extremely hesitant to undertake.

My wife Sue inherited the machine when I got my PowerMac last year, and up until two weeks ago, it was still working well enough for me to keep putting off the inevitable re-install. And then it suddenly decided it didn’t want to send e-mail messages via Outlook any more — even though those accounts still worked just fine on my PowerMac. Something funky was going on with the machine’s network settings, and I reluctantly concluded it was time to take drastic action.

After doing a little research, I determined that Windows XP Professional Edition would be able to run on the machine, and ordered the new OS. It arrived Monday, and I began installing it Tuesday night. I didn’t finish until 11 p.m. on Wednesday.

To say it was a grueling process would be a massive understatement. Prior to XP’s arrival, Sue and I backed up everything on the machine. I wasn’t going to take any prisoners this time around — screw upgrading, I was going to do a clean install of XP and completely exorcise any Me ghosts lurking about.

Ah, the optimism of youth.

This particular machine has a 12 gig hard drive, which Windows 98 partitioned into two six gig drives. The first time I tried to install XP, it said there wasn’t enough space on the C: drive. I didn’t care, since I wanted to blow away what was there anyway, but alas, Windows wouldn’t let me do that. So I decided I’d install it to D: instead. I’m not sure why I did that — I think at that point I was starting to get desperate, and figured I could just re-arrange the drives when I was done, killing off the C: drive and re-allocating that space for something else.

Yeah, right. Once XP was installed, I couldn’t re-format the C: drive, presumably because of the existing Windows Me installation there. Worse yet, the machine was now dual booting, allowing me the choice of which OS to use rather than allowing me to say, nuke the Windows Me installation entirely.

Realizing the folly of my earlier decision to install to D: I decided to re-boot into Me, kill out extraneous files, and free up enough space to do the XP installation. I was momentarily tempted into doing an upgrade of Me to XP, but fortunately, Me crapped out on me before I could — as soon as I removed Office XP and re-booted, Me had a hissy fit and decided to start crashing shortly after it loaded.

Ok, no problem, I thought, I’m planning on overwriting Me anyway. So I re-booted into XP and decided to start the installation over again. After putting the installation files on the D: drive, I rebooted. After re-entering the installation process, I discovered that I now had enough space to install XP on the C: drive … but now I got an warning message informing me that I attempting going to install two operating systems on the same hard drive partition. I was immediately concerned — I didn’t want to OSes on the freaking drive — I only wanted one! Chagrined, I aborted the installation attempt.

Now I learned a couple of interesting things that night, most of them by reading this article on

First off, Microsoft is now assuming that people are using computers that allow you to boot from a CD. Under that scenario, you can simply through your Windows XP CD into the drive, re-boot, and run the whole installation from disc. That’s great … but my computer couldn’t boot from CD.

Second, I could take a few steps backward and download a program that would allow me to create set-up floppy discs. This would allow me to install XP as I did 98 and Me — basically, these floppy discs install very basic operating system functions like CD support, and then allow you to do a full installation. I also learned that Microsoft is planning on phasing out this capability, so when Longhorn finally arrives, everyone’ll need to have bootable CD-ROM drives (though honestly, at that point I’m sure most older machines will be incapable of running the latest version of Windows). At first I was a bit peeved by this, but then again, Macs have been booting from CD for years and don’t even ship with floppy drives any more.

Third, Microsoft recommends that people always do a clean installation onto their computers, rather than upgrade from the previous OS. Now that’s all well and good, but you know what? Microsoft may recommend doing that, but they seem to go out of their way to do make doing that as difficult as humanly possible.

On Thursday night, after fortifying myself with a Sam Adams, I returned to the fight. I decided that I would try to install XP to the C: drive one last time. If it didn’t work, I’d have to create the installation discs and do it that way.

I started off by destroying the D: drive partition — after all, I didn’t need two versions of XP residing on the same computer. I then went ahead with the install. This time, when I hit the “Two Windows” warning message, I ignored it and pressed on … at which point I discovered that the Installer was going to allow me to overwrite the existing Windows Me installation. Now why it couldn’t have just told me that on the earlier screen, I have no idea, but I happily agreed to destroy Me and proceed with the XP installation.

An hour later, XP was successfully installed on the machine, and it was glorious. Despite the fact that it was a more modern operating system with higher system requirements, it ran much faster on the PIII machine than Windows Me ever did. I was somewhat surprised to discover that all the installer did was overwrite the Windows directory with the new operating system; it didn’t format the drive first, so all of my old data files were still on the C: drive (which made restoring the machine easier, but I’m still glad we did the earlier back-ups.

There was only one problem — no D: drive … and no readily apparent way to re-create it. Since the C: drive only had a gig of space left, and I had plenty of programs left to install, I went hunting for a way to re-create the drive via XP. That’s when I found Disk Management, a FDISK like program buried deep within XP’s Computer Management control panel (why this wasn’t included in the more logical “System Tools” menu on the task bar, I have no idea … save perhaps they were trying to keep newbies from accidentally nuking their drives). You can read about it here.

Using that program, I was able to restore the D: drive. After that, it was just a question of getting my programs re-installed and re-enabling printer sharing. After a bit of tinkering, I was able to get the Mac printing to the laser printer shared by the Windows XP machine, and all was well and good within the Newquist home office again.

All of this was horribly time consuming — I managed to watch two episodes of Alias while waiting for XP to install, and another two while I re-installed all of our software. While I like Windows XP well enough — its far more stable than anything that came before, at least on the consumer side — the entire process has intensified my dislike for Microsoft’s OS. Now admittedly, I was doing all this on an older machine, but that said, it should not take me two freaking nights of hard work and research to install a new operating system.

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