Failing to install Windows on your Mac, after Bootcamp let you down, part 1

Where we take the world down with us, and burn it all to the ground. All to play Portal 2. Seems oddly fitting.

Failing to install Windows on your Mac, after Bootcamp let you down, part 1
Windows - Photo by Rob Wingate / Unsplash

Hi! So, long story short, my girlfriend and I wanted to play Portal 2 together. Sadly, Valve never bothered releasing a 64 bits version, so 'recent' macOS versions won't run it. Heck. Steam won't even let us install it.

Running Windows

So what are our options here?

Run the Windows versions using Cross-Over. Sure, why not. But here laptop is a 2015 Macbook Pro, and those already have a hard time running games actually made to run on macOS. Let alone a Windows one on top of a compatibility layer.

So that means Parallels & co are out of the question, because adding all the extra load of a fully-fledged VM isn't going to make things better.

What's left? Good old Bootcamp! Dual-booting macOS & Windows! So let's retrieve that dear old Windows 7 iso, and it's license key...

Oh, no, Monterey is picky. Only Windows 10 or 11. Nothing older. Ok... so let's get ourselves a Windows 11 license then.

Ok, let's start again. The ISO isn't rejected by Bootcamp, good. It even wants to download some Windows support software. Great. Always hated drivers and loved how Bootcamp made it all so easy... Oh, wait.

"Download could not continue. The Windows support software is not available online."

Ok, so what do people suggest?

Manually download the Windows Support Software

The first suggestion appears to be to download the Windows Support Software separately, through the Action submenu in BootCamp's menu bar. Supposedly, downloading it and putting it in the right place will let the BootCamp utility find out it's already been downloaded, and go right to the next step.

Downloaded it. Put it in the same folders as everyone. To no avail.

"Download could not continue. The Windows support software is not available online."

Right. So, what's next?


Brigadier is a nice tool that makes it easy to download the appropriate drivers and software for a Windows install on your Mac. How? Well, first you've got to make a bootable Windows USB drive, then install Windows, then use Brigadier...

Oh. But we don't have a USB key. I mean, we could put her Android phone in disk mode, burn the Windows ISO onto a partition on it and boot from there, but... last time I did something similar, I lost 10 years of pictures, and their backup. So I'd rather avoid it.

What's next? Burning the ISO onto a partition, booting from that, and then installing Windows? Sounds a lot like what Bootcamp must do. But I have no idea how to burn an ISO onto a partition, and couldn't find anything reliable on macos.

Windows 10 BootCamp Error - Apple Community
How to use bootcamp without a usb - Apple Community
Bootcamp windows 10 without a USB - Apple Community

Next? Setup Windows in a VirtualBox VM, but on an actual partition. Sounded like a good idea, at first. But really, avoid it if you can. This requires using one of your hard drive's very own partition to install your Windows virtual machine onto, through a feature called "raw disk access". So I did just that.

First, create a FAT partition, then found it's identifier, and finally setup my .vmdk file for raw disk access.

Except it didn't work. Virtualbox wouldn't set up the raw disk access

Because the command had to be run as sudo. Of course it did.

But even then it wouldn't mount the .vmdk file. Because since it's been created using sudo, it is owned by root. So let's change that too. And... VirtualBox VERR_ACCESS_DENIED. Ok, sure, why not. What is that? Ah, macOS' good old System Integrity Protection is apparently getting in the way. So we can either disable it, or reassign the partition and .vmdk file ownership and group at each boot.

Now, let's start the VM! Starting... aaand... nope, crashed. Some write error. Why? Because the VM's host I/O cache is disabled by default. Let's fix that too.

And, finally, Windows 11 wouldn't install, either because of the SecureBoot or the TPM check. No kidding; it's a damn VM. Let's fix that too.

And now, let's reboot, hold Alt ⎇, and.... !!!

Screwing up the whole drive

Nothing. Just the good old MacintoshHD. Why? Well, the BootCamp partition is probably corrupt. Or somehow not correctly set up as bootable. So let's dive into that. And accidentally screw up the whole partition table by accident.

Good thing I had her move all her hard work into ~/Documents, which is (semi) backed up using iCloud Drive, right? ... right? Oh, no. Looking on the web app, it seems iCloud Drive apparently hadn't been enabled. Well. That's a good way to learn the importance of backups if there ever was one.

Fixing the Mac

(Internet) Recovery Mode

Let's boot the mac into recovery then, and at least get macOS installed and setup before going to bed.

Fun fact. The text might be in French, and the physical keyboard AZERTY, but the keyboard layout is still QWERTY. Always nice when the passwords you type in "secure" input fields that won't display their content contain some of these characters that change places.

Oh, crap, right. The recovery partition is gone too. Ok then. We'll recover the recovery partition using internet recovery. On a hotel WiFi in Western Africa. Because it obviously is the best way to do that.

Or not.

The error code used to be -1008F. Then we removed the Activation Lock. And it still was -1008F. But now it's -2003F. Go figure.

And no. Even though the internet connection isn't great, I still manage to have video calls with my clients (most of which don't drop), play Control on a remote server (with decent-ish input and visual lag), and download a whole Windows 11 ISO in a couple hours. As well as the macOS Monterey installer we'll talk about soon, in less than an afternoon.

Target Disk Mode

So, what's left? We could try to put the screwed up mac in Target Disk Mode. Bet you didn't know your Mac could do that trick, did you? There used to be a Target Display Mode too, but that one's long gone now. Anyway, back on track: Target Disk Mode! Let's see if we could, perhaps, recover some files.

Well, no. Nothing. Don't know if it's because we're using a USB-C cable instead of a Thunderbolt 3 one. Or if there just isn't anything left of that Mac's SDD (which would really be worrying).


See how fast we went from trying to install Windows to trying to recover a royally screwed Mac? That's what you get sometimes when you try to get creative. Sometimes it's wonderful. Sometimes you wish you hadn't thought yourself so smart. What can I say? That's also why those TikTok videos are quite clear about not trying to imitate actual professionals' stunts at home. Except here, improperly prepared (read: without any external backup) and overly-confident people only risk losing one or three decades worth of pictures and side-projects. Good thing there wasn't any of that on that laptop.

Back to fixing the Mac

Reinstalling from an external media (ie, a USB stick)

Get a memory stick

Finding a big enough USB stick in Dakar can be quite an interesting endeavour.

Get a macOS installer (and wait) and follow Apple's instructions

How to create a bootable installer for macOS
You can use an external drive or secondary volume as a startup disk from which to install the Mac operating system.

Setup everything on the USB key, plug it in, boot, hold Alt ⎇, pick "Install Monterey", and...

Why does it go into Internet Recovery? Oh, because T2 Macs won't boot from an external media, unless we have explicitly set it in, you get it... recovery mode!

Ok, well, let's give it a try.

I forgot to take a picture of this one. But I'm pretty sure you won't hold it against me and should be able to easily visualize a black screen, with a gray and black globe, a warning sign in front of it, and an error code below.

Nope, still nothing. But this time it took much longer to fail. And the error code changed too! Considering this to be more or less encouraging, especially since some comments online state that just retrying solved their issue, let's try again! But using the hotel's WiFi instead of the more or less reliable 4G router.

Nope. We're even back to the "-1008F" error code. One last time, for the road?

Did shoot this one though

Still nothing. Ok, what's left?

DFU and restoring the EFI

So, we could... wait to find an Apple Repair center, somewhere in Senegal. Of which Apple says there are none.

We also could entrust our Mac into the hands of some random, anonymous, self-confident repairman, that will obviously promise he won't brick anything. Hoping that he won't simply unsoldier et resoldier some chip somewhere using paperglue or something.

Or, we could ship our Mac back to Apple, and wait for a month.

Or... wait, someone online says that they managed to get around the "-1008F" error by booting in DFU (Device Firmware Update) mode, and restoring their EFI using Apple Configurator. Ok, sure, why not, let's try that! I mean, by this point I'd be willing to try dark magic. Thanks to Xcode, it's not like it'd be that much out of my comfort zone anyway. Thank you, Xcode.

Back to Internet Recovery

Reinstalling macOS Mojave

It all went smoothly. Except the 4 or 5 times I had to start it all over again because the macOS install utility didn't find my internet connection suitably fast enough. Quite a picky one, this utility. But it finally worked... Only to fail by going to sleep. In the middle of downloading an OS, yes. Of all times. Absolutely.

So, let's figure out how to run a terminal in parallel of the installer in Recovery mode, in order to prevent the mac from going to sleep. Done.

And it worked!

Reinstalling Monterey

From the USB stick. Since we have it, we might as well save ourselves a few hours of downloading.

First, enable booting from an external media. For which we need to setup a macOS administrator account. I'll spare you the whole user setup.

So, we create our user. Then, reboot, holding alt.

Pick "Installer Monterey".


Back to square one, with all our data gone.

Wait. Didn't Mojave support 32 bit apps? Ugh.