Windows 8 Upgrade Purchase Nightmare (and Solution)

I decided to upgrade my Samsung Series 7 slate to Windows 8. I was a bit concerned about the upgrade process. However, I figured Microsoft would make it easy for me to give them my money. I was wrong.

Initial Steps

I first went to the Microsoft Store its Windows 8 upgrade page. I chose the $39.99 download option vs. the $69.99 ship media option. I also paid about $19.00 for a DVD.

Upgrade Assistant

I was prompted to download and run the Windows 8 Upgrade Assistant. The program checks the compatibly of my apps and devices with Windows 8. It took several minutes to run. When done, it told me that some of my apps and devices (or more accurately programs which enable me to manage those devices) either may not be compatible with Windows 8, or may have to be reinstalled in Windows 8.

Undeterred, I clicked Next. I then was asked if I wanted to migrate:

  • Windows settings, personal files, and apps
  • Just personal files
  • Nothing

I chose the first option.

Show me the money

Now the upgrade assistant hit me up for money. $39.99 for a 2 GB download, optionally another $14.99 for a Windows DVD. I filled out my billing and shipment addresses. I could pay by credit card or PayPal.

Initializing Checkout Failed

Here’s where the nightmare began.

I tried PayPal on my first two attempts. Both times program said initializing checkout failed.

Each time I tried to pay, I had to re-enter my billing info. However, the compatibility results “stuck” so at least that didn’t have to run again.

Tired of repeatedly entering my billing info, I chose credit card. Same error.

I didn’t bother calling Microsoft Store customer support. I had found them clueless on far simpler issues. So instead I checked with Mr. Google. Turns out I had company. A lot of company. All very frustrated.


Following suggestions in some of the multitude of threads:

  • I made IE my default browser. I am dealing with MS after all.
  • Emptied cache. Seems like a wise precaution.
  • Restarted. Ditto
  • Set up a VPN connection so I was downloading from a different IP address (since I don’t use a split tunnel for obvious security reasons). This step is critical per the threads.
  • Bowed to the East while chanting (three times) “Bill Gates is great.” (May not be necessary but took little time or effort).
  • Again went to the Microsoft Store and downloaded and ran the Windows 8 Upgrade Assistant.

It worked! WTF? Steaming mad

OK … started downloading Windows 8. Paused download. Switched back to my usual Internet connection. Resumed download. Downloaded completed and checked. We’ll see how the upgrade goes, but at least the purchase nightmare is over.

Double Billing?

Well maybe. Not sure if I got charged more than once (as others reported they did).

On PayPal, the prior failed attempt was reversed:


The credit card website does not show an attempt, but then again, it may not be updated in real time.

Closing Thoughts

Microsoft, get your act together.

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