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@eddieh
Created December 17, 2019 02:10
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Build Your Own Windows Vagrant Box

Intro

I have found myself needing to test on Windows frequently. I need to be able to spin up fresh virtual machines—Vagrant seems to be the perfect solution.

I primarily use Macs for development and am currently using a cross compiler to develop native Win32 apps (and eventually Win64 apps). On the Mac side, basics like Homebrew are assumed to be installed.

Vagrant needs a virtual machine package like VirtualBox or VMWare installed to function. Vagrant does not install the VM software. You need to install the VM software yourself. In Vagrant parlance the VM software is called the “provider.” I strongly recommend using VirtualBox and for now ignoring that you can use any other provider.

The next assumption is that you own recent version of Windows 10 that has OpenSSH as an installable feature. That is, Windows 10 1809 or newer.

I found the Vagrant documentation to be entirely unhelpful and difficult to follow for getting a Windows 10 box up and running. I generally find Windows to be annoying to use at best and downright unusable for serious work. As such, I don’t care about doing anything the Windows way, I’m going to go out of my way to use CMD or PowerShell for everything. And I’ll be cursing at every dumb little aspect of Windows along the way. You’ve been warned.

Installing the Necessary Software

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