I’ve been using Apple computers and OS X as my primary operating system since Mac OS X Leopard first launched in 2007. During that time, I’ve always kept Windows close by via Boot Camp and virtualization software. There are several Windows-only games I own, and I still use a small handful of Windows apps that I haven’t yet found a suitable Mac replacement for. Plus, being a programmer and techie are other good reasons to keep Windows around; I like to stay current and to keep my software options open.

So, in the name of staying current, I decided to preorder Windows 8 Pro even though I knew I wouldn’t be using it as my primary operating system. The price of entry was low enough to justify it.

I’m now tinkering with Windows 8 and am forming initial impressions, but that’s not what this post is about.

Preordering

When I first set out to preorder Windows 8, I figured I’d do it through Amazon since I had both an Amazon Prime membership as well as an Amazon gift card balance. I was delighted to see that Amazon and Microsoft had set up a promotion where preordering the retail boxed version of Windows 8 Pro for $69.99 would yield buyers a $30 Amazon gift card one month after purchase. This effectively brings the price down to $39.99, which is what Microsoft currently charges for the downloadable (non-boxed) version of Windows 8. Although I don’t have the gift card in hand yet, I figured it would be good to have an official, boxed copy of Windows 8 Pro for effectively the same price as the downloadable version, so I sprang for it. As I write this, Amazon’s promotion is still running.

I ran into two points of confusion when preordering Windows 8 Pro.

First Point of Confusion: Architecture

Amazon’s product page had no indication of whether I was preordering a 64-bit or 32-bit version of Windows; there was only a single “Microsoft Windows 8 Pro” product available for preorder. Because of this, I figured both versions were somehow included in the box, and I turned out to be right. Two installation DVDs are provided in the box, one for each architecture. I wondered how less technically-inclined users would know which disc to pick, but then I noticed that the included “Welcome” card tries to help:

1. Insert a disc. Choose 32 or 64-bit. If you’re not sure, start with 32. We’ll let you know if you need to switch.

I don’t know why Microsoft didn’t print that information on the paper DVD sleeves directly (all they say on them is “32” and “64”) in addition to the “Welcome” card. At least that information appeared somewhere.

But I digress.

Second Point of Confusion: License Type

Amazon’s product page also had no indication of whether I was preordering an “upgrade” or “full” copy of Windows 8 Pro; again, there was only one version available on Amazon. I figured there must be no longer be distinct “Upgrade” or “Full” versions like there have been for previous versions of Windows. To its credit, Amazon’s product page did indeed contain a lot of information about upgrading to Windows 8 from existing Windows installations, but nothing about installing Windows 8 from scratch. Amazon showed (and still shows) the list price of Windows 8 Pro as being $199.99, so I figured I was probably preordering a “full” version, except with a preorder discount or something like it.

BROKEN.

I believe the architecture and license information could have been made clearer. How could I truly have known what I was buying? Other Amazon customers apparently had the same questions since the product page now contains forum threads for both topics.

Neither of these questions stopped me from preordering Windows 8 Pro. I figured that since there was exactly one version of Windows 8 Pro available for preorder, it was the version I needed.

I was wrong.

Installing and Activating

I chose to install Windows 8 inside a Parallels virtual machine on my Mac. The installer prompted for and accepted the provided product key, and the installation appeared to go smoothly. Once Windows was installed and running, I figured it would have to be activated. (I’m not sure that the average user would be able to easily find the activation utility in Windows 8, never mind being aware of the activation concept, but that’s a different story.)

So, I typed my product key into the activation utility and double-checked that it was typed correctly. After pressing the “Activate” button, I was presented with this utterly, completely unhelpful error message:

This key didn’t work. Please check it and try again, or try a different key.

BROKEN.

What “didn’t work”? Did Microsoft somehow issue me an invalid key? Were there network issues? (I was able to use Internet Explorer inside the VM to reach the Internet so I doubted that was the problem.) What was I supposed to do now? There were no other instructions or contact information accompanying that error message.

So, I Googled for the contact information for Microsoft product activation support.

After calling the 888 number, I had to answer a bunch of automated prompts, none of which had to do with Windows 8. I kept having to answer “other” to all of the prompts. After completing the prompts and being on hold for 10 minutes, I was finally connected to an agent who thanked me for calling the support line for “Microsoft Volume Licensing” (a red flag.) After explaining the problem to the agent, he said he’d have to connect me to another agent. After 2 minutes on hold, another agent picked up. Unfortunately, it was impossible to figure out what she was saying. The audio was so severely distorted that I could just barely make out her voice telling me that she couldn’t understand what I was saying. I hung up in exasperation.

BROKEN.

Why were the automated support prompts not updated for a brand new, high-profile product launch, so I could have been connected to the correct agent on the first try? Why, after finally getting connected to someone who supposedly could have helped, were there severe audio issues that appeared to be on Microsoft’s end?

I called back a second time, angrily went through the same unhelpful prompts again, and waited on hold some more.

I was eventually connected to an agent with an Indian accent who introduced himself as “John”. He didn’t mention anything about Volume Licensing like the previous initial agent had. He asked if I was doing an upgrade install, and I told him I wasn’t. He asked if there was any error code that started with “0x” on the screen, and I told him there wasn’t. I read my product key to him, and he told me it looked valid and that he’d have to transfer me to someone else to get the issue resolved.

Fine.

Maria, who was the fourth and final Microsoft support agent I ended up talking to, finally set the record straight: Full retail keys for Windows 8 Pro are not yet available for purchase at all. I had purchased an upgrade key which would only activate Windows 8 Pro after having upgraded from a previous version of Windows.

In spite of that, Maria was able to walk me through manually activating Windows via the mstd.exe utility, entering a single-use code that she gave me.

OH-SO-VERY BROKEN.

How was I supposed to know I had purchased an upgrade-only license?

I eventually figured out that I should have gone to Microsoft’s page for purchasing Windows 8 instead of Amazon’s product page, and I should have read the fine print at the bottom:

* Offer valid from October 26, 2012 until January 31, 2013 and is limited to five upgrade licenses per customer. To install Windows 8 Pro, customers must be running Windows XP SP3, Windows Vista, or Windows 7. Get the full details on our special offer.

Thanks for making it so obvious, Microsoft.

Discounting that, how was I supposed to know that was what the specific activation problem was, based on the error message I saw? One of the agents I spoke with had been asking about a “0x” code, and Microsoft’s “Why Activate Windows” page revealed why:

You upgraded to Windows 8, but didn’t have a previous version of Windows installed (error 0xC004F061)

If you see error 0xC004F061 when you try to activate Windows 8, it means that you’re using a product key for an upgrade version of Windows 8 and a previous version of Windows wasn’t on your PC when Windows 8 was installed. To install an upgrade version of Windows 8, you must already have Windows 7, Windows Vista, or Windows XP installed on your PC.

If you formatted the drive before the upgrade version of Windows 8 was installed, you won’t be able to use your upgrade product key to activate Windows 8. To activate Windows 8, you’ll need to install your previous version of Windows, and then reinstall Windows 8. For help with the activation process, contact support.

That code never appeared for me.

It took four different Microsoft support agents to even figure out the root cause of the issue, even though I had told one of the intermediary agents that I wasn’t doing an upgrade install after being asked.

Buying Windows 8 is Broken.

In doing some quick research for this post, it appears that many bleeding-edge techies who use Windows as their primary operating system were aware that the initial Windows 8 release would only involve upgrade licenses, and I even found a guide that explains how to trick the activation mechanism into allowing activations using an upgrade product key after a clean install.

However, it’s clear that there were also many people who weren’t aware of this.

Maybe Amazon is partially to blame for not making the license information clearer on their product page. At least Microsoft’s page had fine print.

I now know the problem can be resolved by installing a previous version of Windows (wasting time, for the sole purpose of upgrading it to Windows 8), or via workarounds like calling Microsoft or using the hack mentioned above.

Either way, I didn’t buy what I thought I was buying, and the entire experience was frustrating and shouldn’t have been necessary.

BROKEN.