Windows 7 Upgrade experience – A tale of woe

I thought I’d post my upgrade experience from XP 32 bit to Windows 7 64 bit.

I had read that I’d need to install over a clean XP, so I formatted a 500MB drive in my Mac pro and installed XP last night. That failed, because the drive was formatted as a Mac volume, and XP only reformatted the partition. My bad.

So I ran the Boot Camp Assistant and let it wipe the drive and prepare it for Windows. That install went fine.

1:30pm Today I receive my Windows 7 Home Premium Upgrade from Amazon. On the front of the box, it says “Windows 7 Upgrade designed for Vista.”

Uh, I have XP. Hmm. Ok I look on the back. On the back it says:

“This version of Windows 7 is designed as an upgrade for Windows Vista(r). If you are upgrading from Windows XP, you will need to back up your files and settings, perform a clean install and then re-install your existing files, settings and programs. Visit for important information.”

Ok, so I have to perform a clean install. Of what? XP? 7? Can I do a clean install with this version?

Now on the side of the box it reads:

Attention: All editions of Windows XP and Windows Vista qualify you to upgrade. You must accept the enclosed license … go to”

Ok so that is two URLs so far.

Now on the bottom of the box it reads:

Windows 7 Upgrade Advisor can help you determine which features and editions of Windows 7 will run on your computer; visit

lol, so three URLS and two having “windows.” has the root and the other having “www.” as the root.

1:50pm So in XP I go to the upgrade advisor, which makes me install an ActiveX control, which in turn makes me install .Net 2.0. I still haven’t opened the box, mind you.

I’d be done installing Snow Leopard by now, for whatever that is worth.

Now the “advisor” is saying that I can only install Windows 7 32 bit. Which is nonsense, because I had used Windows 7 64 bit betas all year. And it says my graphics adaptor, an nVidia 8800GT can’t handle AERO, the Windows UI answer to Apple’s Aqua. But I know it does!

Ok that was a total waste of time and a total failure.

Anyway, forget that, I’ll just stick the disk in and see what it does.

The package comes with two DVDs, one 32 bit, one 64 bit. The DVDs are covered in holograms and includes “Windows Anytime Upgrade” whatever that is.

Let’s try the 64 bit disc, because I need that to access all of my memory.

The instruction manual says if I am upgrading from XP, I need to take special steps and choose Custom (Advanced) upgrade.

So let me get this straight? Most of their user base is still on XP, and they made that upgrade path the hardest?

I insert the 64 bit disc and it says:

This disc isn’t compatible with your version of Windows. For more information, check your computer’s system information. (For what? lol) To install a new copy of windows, restart (boot) your computer using the installation disk and then select Custom (advanced)

Let’s see what happens if I boot off the 64 bit installer DVD.

1:58pm I see a Windows XP screen. Oh it booted into my XP. Sigh.

Am I having fun yet?

Well, it won’t let me boot into 64 bit, when I Windows 7 beta did.

Awesome, now I get to call Microsoft.

Amusing, on the cover of the included literature it reads:

Welcome to your PC, simplified. Windows 7

Ok now I am on the phone with Microsoft.

2:17pm Ok wow, just wow. The guy opened a case number for me, didn’t give it to me, transferred me and then it said, and I am not joking, “Oh oh! Received data error!” and hung up!

So now I am calling them back. Now I have someone asking me for my 9 digit installation code? She asks if I am trying to authorize Windows. I say “No, I am trying to install” So then she tells me she’ll connect me to technical support. Sigh. Then she gives me an 800 number to call in case I am disconnected. Oh wait, that number is wrong, she gives me the following number: 866-613-0270 5am-9pm PST

2:28pm Ok, now I am being transferred, again.

2:31pm Now they are figuring out what support I am entitled to, again. This time they took my product key and are validating it. I’m sure someone at Apple is chuckling, or maybe crying, by now, at what Microsoft puts its customers through.

2:39pm Now this person authorized my retail copy of windows, given me yet another 800 number and has transferred me.

2:49pm After explaining 5 times what I am doing, I was put on hold. But while on hold, I figured it out.

I used the Windows Boot Camp Startup Panel to choose the DVD to boot from, and now it is booting off the DVD.

Ok the guy came back and informed me that they don’t support installation onto Macs.

However, he did go ahead and tell me how to complete the install, because it will fail he said.

2:56 pm First, I have to choose custom install. So I did and chose my drive. It warned me a previous Windows existed, and I said ok.

3:04pm Windows reboots. Setting up registry settings. Starting services.

3:07pm Completing installation. It informs me the computer will reboot several times during installation.

3:19pm It is now asking me to enter my user info.

Next, he said when it asks for a product key to skip entering the product key. So I do. I answer a few more questions and it continues.

Next, he said once windows boots, try to install windows a second time and then do a upgrade install (not custom), and then enter the product key, as the product key I have is only for upgrades.

Yow. So he told me how to work around their DRM. Why even have this crap in the first place?

3:28pm At the desktop, second install started, this time an upgrade.

Another amusing anecdote. I just got an email from MS about my case:

It was my pleasure to work with you on your Windows service request XXXXXXXXXXXX. Unfortunately, we were unable to resolve your issue. However, I hope that you were happy with the service provided to you.


Back to the second install. Still copying files.

3:39pm Rebooting to finish install.

3:52pm Another reboot, it’s transferring files and settings, I guess from the previous empty install. Maybe it is keeping my user, I don’t know.

4:04pm It’s rebooting again. It had to copy over more settings. Which it had just installed.

4:08pm Entering the product key now. That seemed to have worked ok. Logging in.

4:11pm Finally, I’m at the desktop.

I am not going to install any Boot Camp software, as Apple said support will be coming before the end of the year.

Two Hours, Forty-One minutes. Excellent user experience, Microsoft.

Aero works and I am in 64 bit. So the advisor is a pile of trash. Don’t trust it!

Snow Leopard has one installer. One. It installs both 32 and 64 bit OS and apps. It took 30 minutes to install. It does upgrade or full installs. You can change the kernel with 3-2 and 6-4 at boot time. That’s it.

These experiences are good for me as a Mac user. They truly make me appreciate how much hard work Apple does under the scenes that we take for granted. Macs are not perfect, but they’re no Microsoft OS, either. Count your blessings, Mac users.