Dear Diary: Windows 10 on 2008 vintage Macs

A local eRecycler is enabling me to develop kind of a thrilling computer-hording neurosis. I’ve managed to score 4 17″ MacBook Pros and 2 15″ units ranging from 2006-2008 vintages and it’s cost me very little. Some of these have serious problems, no matter, I’m having fun.

The 2008 Macs top-out at macOS 10.11, which is good for now. There’s some room to bump them over the edge in to Sierra, though I’m kind of pissed at Apple’s business model at the moment. I feel they’ve kind of abandoned the desktop entirely and the old machines are getting shafted the hardest. Granted they ARE old, Moore’s Law’s been on vacation for a while now. I guess we live in a sad world and anyone who buys a new Mac Pro will arrive in this well-populated sad space in about a year. 4,5,6 Apple. Seriously wtf? I know.. I know, it’s just business and the best margins are mobile. But I seriously digress.

These old machines that max out at 4-6GB of RAM. Microsoft sells new machines running Windows 10 on 2GB of RAM. I’m sure they lick the well-toned ass of satan (not a good thing, in my books). These wimpy new machines still have to at least pretend to work, which has a modicum of merit. So, disgustingly, Windows could become the best option for folks with ancient macs that won’t die. (Yes, there IS Linux. I’ve used Linux daily for ~17years, I love it. It’s complete shit on the desktop, if you wanna argue that, then you know, that’s cool, you’re welcome to be wrong. IT IS the Trump-era now, so anything goes)

I discovered that if you’re willing to commit a Windows License to a specific machine, then you can get a non-transferable license, called an OEM license for a vastly lower price. I actually talked with Microsoft’s online sales about this and they said they only sell the Retail version ($150) to end customers. The retail version has the notable merit of being a transferable license. I showed the Microsoft rep a kind of a greasy-looking OEM license vendor I found online. Microsoft’s rep didn’t call the OEM vendor a scam and said it is an actual option. So I think it’s fully legitimate, which actually matters to me. Ultimately, I found an OEM key from an ebay vendor that I think is legitimate for $7.50. I would think THAT would have to be scam, but there were hundreds of positive ebay reviews, guess we’ll see. $7.50 is a price I’ll actually pay, so here we go with Windows. My core hope is that Starcraft II run better enough under Windows to enable me to equip some friends who want to play with me, but lack systems that can swing it.

It’s been about 7 years since I goofed with native Windows on an Intel Mac, so I had to relearn a couple things and keep fighting. After many hours and lots of music, it seems I’ve got a nice dual boot setup going.

Here are my steps, if nothing else, I’m documenting them here so I can figure my way back through this shitshow again at a later date…

Get a viable installer

Get the Windows ISO from Microsoft. After much fuckery I realized my failures to get the installer to fully boot are a common pain-point, with common, decently-documented resolutions. For the 2008 vintage, installing from USB is probably possible, but I didn’t try it too hard, it certainly got no further than with DVDs.

I followed the steps from here to make an installer that actually worked. The steps are copy and pasted below in case that site dies:

1. Download Vista SP1/2008/Windows 7 x64 ISO from MSDN (Microsoft), or grab your CD
2. Create 3 folders c:\efi-iso c:\efi-exe c:\efi-dvd
3. Download oscdimg.exe from here and extract into c:\efi-exe
4. Extract iso using 7-Zip or WinRAR (Or copy the contents of the DVD) into c:\efi-dvd
5. Start up a command prompt (Start -> Run -> cmd)
6. Type: cd c:\efi-exe
7. Type: oscdimg -n -m -bc:\efi-dvd\boot\ c:\efi-dvd c:\efi-iso\windows7.iso

The oscdimg.exe has been copied here too, because I trust the internet to die and I want a copy in my blog archives.

Now you should have a viable installer. I’ll add that in my case my 15″ unit’s DVD drive was struggling and I think it was a hardware fault. I temporarily swapped-over a drive from a 17″ unit and that worked, but I had to operate the drive physically raised out of the machine body. NOTE that these slot loading drives don’t obscure the internals and you can see the laser inside. Most of these drives are class III lasers that CAN cause eye damage, so, you know, be careful and proceed at your own risk and with caution. Safety above all else.

Also, I figured putting in an SSD is smart. I like SSDs for not dying when you use your computer to chop-down a tree (while it’s running); they handle blunt-force trauma very well. On these older machines, you’re limited to SATA 1, so that sucks a lot, but that’s still faster than what I’d expect to get for throughput from a mechanical drive, especially a shitty 5400rpm one. That’s right, I bought a $20 computer and then put in a $100 drive. Look, I told you this is a neurosis. So. Moving on..


I still like macOS and wanted a dual boot. The Boot Camp Assistant will tell you to suck on a rotten egg at this point, so forget about using it. Though I did use it to fetch me the Windows Boot Camp drivers.

To make room for Windows, I booted from a macOS installer and used the Disk Utility to non-destructively add a partition. I used to boot a Live Linux environment and use GParted for that purpose, so that probably would also work.

Tangent: During my quest to boot a vanilla DVD, I installed refind. It can help a lot of pretentious boot situations. However with my patched DVD, refind didn’t even see this as a bootable volume.

Pressing and holding the option key at power-on led to the Apple EFI boot menu, which saw the DVD and called it “Windows”. This actually booted the installer.

With the Windows installer going, I reformatted the Windows partition I’d just made and the install was fine. After installation, I still had to use the Option key to select Windows to boot. I’m sure that can be changed to the default through the Target Disk gui in macOS (maybe it’s called something slightly different, whatever).


Out of the box, Windows sorted enough crap out that I didn’t strictly need boot camp drivers. But I wanted them because in the past, they’ve smoothed over some stuff significantly. Things like the keyboard back lighting, display brightness, trackpad settings, etc. Well, naturally, Windows wouldn’t run the Boot Camp setup program because it has a bunch of conditions no longer being met. (Some older Boot Camp drivers can be downloaded from here)

This is also a documented pitfall, the main thing that got me through was this. However, I still had to do something extra. Here’s what I did, which let the installer run:

  1. Open Explorer and navigate to the Boot Camp drivers, go in to Drivers\Apple and right-click on the BootCamp64.msi file. In Properties, assert that the Compatibility mode is for the version of Windows that the drivers were actually for. Make sure you make these settings apply to all users. I actually had to do this a few times, it was as if I’d cancelled out, though I had not.
  2. Run CMD as Administrator. (You may need to connect an external mouse just to right-click)
  3. Navigate the shell to your Boot Camp driver folder that the Boot Camp Assistant gave you.
  4. Enter the sub-directory Drivers\Apple and run msiexec /i BootCamp64.msi

That got the Boot Camp driver installer to run for me. Others may then get stuck where I did, where the SigmaTel driver installation never completes. I got around this by just getting rid of the IDT SigmaTel directory in the Drivers directory. (I actually just moved it out of Drivers and in to a new directory I made called Drivers-PenaltyBox)

Here’s proof I got the drivers installed. This was probably most valuable to me for getting tap to click (and two-finger tap to click working with the trackpad).

Living with Windows

So the first thing I did once I was using my setup was to go get Firefox. I opened up Edge and typed in to the search/address bar “Firefox”. The first thing that comes up looked right at a glance, but then I promptly realized it was a phishing site peddling adware. So, you know, great job Microsoft Bing & Edge. The very first site you take me to tries to shit on my desktop maliciously. Sigh. Still totally worth $7.50 to have a modern OS, even if it does hate itself, just a little.

Thankfully, I caught it before running the fake Firefox installer.

Sigh.. Right.

Is it worth it? We’ll see. Nevertheless, that’s what it took to get me up and running. For the hourly rate I work for, I could have just put in extra hours and used the proceeds to buy a new computer, but I don’t at all need that one bit. It’s about the deranged journey.

Tee hee…

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