Headless Windows Setup (WSL + OpenSSH)

0.create_vm.sh

#!/bin/bash

# Run this on the VM host

DOWNLOAD_URL=<download url> # Go to https://developer.microsoft.com/en-us/windows/downloads/virtual-machines to get the latest download url
VMNAME=UniversitySite
CPUS=6
RAM=10240

# Download VM from Microsoft
aria2c -s 16 -x 16 $DOWNLOAD_URL -o WinDev.zip

# Extract zip
7z e WinDev.zip

# Import virtual appliance
vboxmanage import WinDev.ova --vsys 0 --vmname $VMNAME --cpus $CPUS --memory $RAM

# Configure networking
#
# Setting the mac address isn't necessary, but it will ensure that recreating the VM on the same host will maintain the same DHCP assignments (i.e. IP)
vboxmanage modifyvm $VMNAME --nic1 bridged --bridgeadapter1 enp2s0f0 --macaddress1 080027B514B5

# Enable remote desktop
vboxmanage modifyvm $VMNAME --vrde on

# Clean up
# rm -f WinDev.zip WinDev.ova

# Start it up
vboxmanage startvm $VMNAME --type headless

1.configure_wsl.sh

#!/usr/bin/env bash

# RDP into the VM and run this in the WSL.
#
# The default password is "password"

# Configure port to 2222
sudo sed -i -e 's/Port 22/Port 2222/' /etc/ssh/sshd_config

# Enable password-based authentication (recommended to set up keys once you're able to use ssh-copy-id,
# see the comment at the bottom of the last script).
sudo sed -i -e 's/PasswordAuthentication no/PasswordAuthentication yes/' /etc/ssh/sshd_config

# Generate new server certs
sudo dpkg-reconfigure openssh-server

# Start ssh
sudo service ssh start

# Append Windows PATH (so you can run native Windows exes. You usually get this by default
# with the WSL when launched with `bash` or `ubuntu` from a powershell session because it
# will inherit the existing path, but you lose out on it when logging in via SSH due to no
# parent powershell session).
echo "WINPATH=\$(/mnt/c/Windows/System32/WindowsPowerShell/v1.0/powershell.exe -Command \"echo \\\$Env:Path\" | sed \"s/C:/\/mnt\/c/g\" | sed \"s/\\\\\/\//g\" | sed \"s/\ /\\\\\ /g\" | sed \"s/;/:/g\")" >> ~/.profile
echo "PATH=\"\$WINPATH\$PATH\"" >> ~/.profile

2.configure_vm.ps1

# Run this in an elevated (administrator) Powershell session in the VM

# Punch a hole in the firewall for the SSH server we installed in the WSL (which shares the host's networking)
Import-Module NetSecurity
New-NetFirewallRule -Name WSL_SSH -DisplayName "Allow SSH access to WSL" -Enabled True -Profile Any -Action Allow

# While we're here, set the hostname to something nicer and reboot to apply
$(Get-WmiObject Win32_ComputerSystem).Rename("<hostname>")
Restart-Computer

# If all was successful, you should be able to ssh into your VM from the LAN (provided the VM host firewall permits it)
#
# `ssh -p 2222 user@<hostname or ip>`
#
# If that doesn't work, check the VM host firewall, and ensure the SSH server is running in the WSL (`service ssh status` and `service ssh start`)

# From here, it is recommended to do basic linux setup and hardening. If you don't know how to do this, see here:
# https://www.digitalocean.com/community/tutorials/initial-server-setup-with-ubuntu-16-04

README.md

Headless Windows VM Setup

These scripts contain the basic procedure to import a new Windows development VM to VirtualBox and set it up for headless usage via SSH.

It is not a headless or unattended install; don't run these and walk away expecting to come back to a ready to use setup. You will be prompted for input as times.

To use, read each script, and run it in the specified environment.