My awful experience installing Windows 10 in VMWare Fusion 8

In reviewing Lance’s performance at the Spanish national championship this past weekend, the GM trainer from Andalucia strongly encouraged us to buy “ChessBase” as a tool to keep up with the latest in opening theory. Since Lance already runs Windows 7 in VMWare Fusion—in order to run PlayChess and TeamSpeak—I didn’t expect there to be any issues installing ChessBase (which is only available for Windows.)

I was wrong. Trying to install ChessBase in Windows 7, I got an error that some C++ runtime was missing. I downloaded the runtime from the link included in the error message, but it wouldn’t install either.

Not wanting to waste time on all this, I figured the best way forward would be to just update to the latest Windows—i.e. Windows 10. And so began the following nightmare:

1. When you go to the Microsoft store to buy Windows 10, you’re presented with three options—(1) Free upgrade for Windows 7, 8, or 8.1 (2) Buy Windows 10 (Download), and (3) Buy Windows 10 (USB – English). (I’m not sure why “English” is listed on the USB option…)
2. Here’s what you see when you click the free upgrade option—a screen that suggests you buy a new PC, and provides zero information about how to upgrade. Heavy sigh, but having to jump through hoops to get something free didn’t strike me as surprising.
3. Again not wanting to waste time, I decided to just buy the thing. And the purchase process turned out to be a lot more straightforward than the free upgrade process, as expected.
4. After my purchase, I had to choose which version to download: Windows 10, Windows 10 N, Windows 10 KN or Windows 10 Single Language. Of course, there’s no explanation of what the differences are, so I just rolled the dice and chose the first.
5. Then you have to choose “Home” vs “Pro”. Again, no explanation of the differences, so I just chose “Home”.
6. Then you have to choose 32-bit or 64-bit. You’d think Google could help with this, but not really. Rolling the dice again, I just went with 64-bit. Bigger is better, right?
7. I was then given a download link to an .iso file, and product number. I downloaded the .iso file, and used it to start the process of creating a new VM in Fusion 8. Fusion asked for the username, password and product number—all of which Windows later asked for again.
8. When the Windows 10 installation window opened, it asked for the product number. I entered mine, and was told the number was invalid. Of course. After a bit of Googling, I learned that you actually don’t need a product number to install Windows 10 (Was my purchase for nothing?) so I clicked, “I don’t have a product number”.
9. The next screen asked if I want to do an “Easy Install” or a “Custom Install”. According to Google, one shouldn’t touch the Custom Install!
10. Clicking “Easy Install” led me to a screen saying that I’d booted my Windows machine from “Windows Installation Media”, and that I needed to disconnect that, reboot windows, and then re-insert the media when prompted. WTF!?! Now, you would think that somebody else would have ran into this, and you’d also think that VMWare Fusion themselves would have run into this while installing Windows 10, but the internet offers no solution to this problem.
11. In desperation, and feeling I’d hit a complete dead end, I decided to give the dreaded “Custom Install” a try. I clicked that, surprisingly wasn’t asked to make any custom choices, and the Windows 10 installation proceeded to complete successfully. Un-believ-able.
12. In order to get reasonable integration with your Mac, the first thing you have to do when a new VM boots is install “VMWare Tools”. Unfortunately, for me, the “Install VMWare Tools” menu item was grayed out. Google said the problem is that VMWare Tools requires a virtual CD-ROM device to be attached. (Why on earth?!?…) Unfortunately, in my case, there was no way to add a CD-ROM to the VM, because neither my MacBook Air nor Lance’s iMac have a physical CD-ROM! Trying to add one anyway using the “Auto-Detect” setting led to a boot error, “Can’t attach to the Sata 0.0 device”. And again, unthinkably, neither the VMWare website nor Google could seem to help!
13. The solution, as I eventually discovered, was to manually download VMWare Tools (which of course comes with no README; just a bunch of .iso files), attach the Windows 10 VM’s CD-ROM device to the “Windows.iso” file included with the VMWare Tools manual download, boot the VM, and then install VMWare Tools manually from the attached “virtual CD-ROM”. Apparently, this was only needed on the first installation of VMWare Tools, and that in the future it’ll be able to upgrade itself without a virtual CD-ROM attached. We’ll see…

At this point, almost five hours later, I could finally install ChessBase under Windows 10, and provide it access to our shared network device.

To me, it seems absolutely crazy that it hasn’t occurred to anyone at VMWare to write up a tutorial documenting what I imagine is a common use case of someone wanting to purchase Windows 10, and then create a Fusion VM, with VMWare Tools installed.

Update—After posting this article, a couple other observations came to mind, illustrating just how crazy this Windows world is:

• When you install MacOS, you’re shown a progress bar. The progress might not be accurate, but at least you’re shown the visual indication that something is happening. When you install Windows 10, you get a screen that shifts between dark and light blue (is it breathing?) and says, “We’ve got some great features waiting for you.” It’s not really clear that something is going on in the background. In fact, at some point, I clicked the screen just to make sure it wasn’t waiting for me to do that to continue!
• The biggest hilarity happened when installing ChessBase. The first time you launch the app, it asks you to enter its product code. That’s normal. What’s not normal, though, is that it also asks you to respond, on the same screen, to a CAPTCHA! Can you imagine? An installer with a CAPTCHA! But it gets worse. All the letters in the CAPTCHA are capitalized, and the input field auto-capitalizes whatever you type in, which, OK, seems to make sense if they want to remove case-sensitivity from the operation. But here’s the thing—if you type in a lowercase letter, even though it gets upper-cased in the input-field, the lower-case letter gets sent to the validation, and IT IS case-sensitive! So even though it looks like you’re submitting an upper-case letter, you’re not! Insane!