FreeDOS dual boot with Windows 7/8/10

Sat, 03 Dec 2022 16:55:11 GMT

Posted by: isaacschemm

I've got a Dell Dimension 4700. It's a 32-bit PC from the mid-2000s, and it's just barely new enough to have a PCI Express slot, which I used to add USB 3 ports, including a type-C, on a front panel (mostly because I thought it was funny).

The only actual work I do on this computer is writing, and the only way I can concentrate on writing is if my computer doesn't let me do anything else, and doesn't show anything else on the screen. That's why I do all my writing in Word 5.5 for DOS. For editing, I usually like to use Word 97 (with doswrd32.cnv), then export to HTML and copy to a thumbdrive.

I'd also like a Debian installation on there, just in case it comes in handy for some random project, but I don't want to commit to not touching it. There's a good chance I'm going to want to overwrite the installation at some point in the not-too-distant future - either by installing over it (maybe with a newer version), or removing it to make more space in my Windows partition for storing some big ol' files - and I don't want that to break my bootloader.

So I need to be able to:

Boot into FreeDOS
Boot into Windows (this computer's got a Windows 7 license, so that's what I'm using)
Boot into Debian on the rare occasion I need it
Delete the Debian partition without breaking the ability to boot into the other environments

In a normal triple-boot, you'd probably do something like this:

Install Windows 7
Install FreeDOS
Install Debian using the rest of the available space

In this situation, Debian installs GRUB 2, which allows you to boot Windows 7 or FreeDOS instead.

But I don't want to commit to my Debian installation - I'd like to be able to overwrite or remove it, and still boot the other two operating systems on the drive. So what I want is a system that asks if I want Windows 7 or FreeDOS, then gives me a sneaky way to boot to Debian instead if I'd like. Turns out there's a setup that works really well in this very specific situation, and doesn't need any external boot disks. I'll walk through it below.

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FreeDOS dual boot with Windows 7/8/10