Windows 8 was broadly available on October 26. I was trying to upgrade one of my laptops from Windows 7 to Windows 8 Pro using Windows.com for $39.99. I got this error “initializing checkout failed” error on the Windows 8 Upgrade Assistant final screen.
Windows 8 Pro upgrade is very cheap. It is just $39.99. Most people may want to upgrade to Windows 8 Pro. I tried to upgrade it today. I was able to run Windows 8 Upgrade Assistant. It displayed Compatibility Issues. It’s all good. I was ready to upgrade. I entered payment information etc. When I was ready to upgrade on the final screen, I get this error “initializing checkout failed” error.
Frustrating Part was there is no back button or retry button. I had to start it all over again & enter payment information etc again. I got the error again. It seems Windows 8 upgrade payment processor was having issues. Solution was to try to upgrade little later. I think everyone was trying to upgrade and payment processor was working. That was a bad thing.
Finally I was able to start the upgrade process later in the day when I tried it again. You may want to take note of below things
1. Make sure your computer or laptop does not have option to turn it off automatically. Windows 8 upgrade download is about 2GB. It will take some time to download it. You may want to turn off “Put the computer to sleep” option in Power Option. Just double click on your battery icon in the system tray to get to it.
2. If you don’t have good internet speed, you may want to order Microsoft Windows 8 Pro