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Bootstrap Vagrant and Rsync on Windows
Write-Host -ForegroundColor green "Bootstrapping machine"
Write-Host "Setting up package management and installing required packages for Dev."
# Install Choco (if not already installed) + required packages
if ( (Get-Command "choco" -errorAction SilentlyContinue) ) {
Write-Host "Chocolatey already installed. Skipping."
} else {
Write-Host "Installing Chocolatey"
$wc=new-object net.webclient; $wp=[]::GetDefaultProxy(); $wp.UseDefaultCredentials=$true; $wc.Proxy=$wp; iex ($wc.DownloadString(''))
Write-Host "Installing required packages."
choco install cyg-get
If ( -not ($env:path | Select-String -SimpleMatch "cygwin") ) {
Write-Host "Adding cygwin to path"
$userPath = [Environment]::GetEnvironmentVariable("PATH","User")
$userPath += ";c:\tools\cygwin\bin"
$env:PATH += ";c:\tools\cygwin\bin" # For this session..
[Environment]::SetEnvironmentVariable("PATH", $userPath, "User") # Permanently
Write-Host "Packages installed"
Write-Host "Configuring Cygwin for use with SSH"
# Setup SSH / Rsync for use with Vagrant
C:\tools\cygwin\cygwinsetup.exe --site --quiet-mode --packages openssh,rsync
# TODO: Add to Git Bash Path /c/tools/cygwin/...
Write-Host "Cygwin configuration complete."
$env:PATH += "c:\tools\cygwin\bin"
Write-Host "Installing Vagrant and friends... This will take a little bit of time"
if ( -not (Get-Command 'vagrant' -ErrorAction SilentlyContinue)) {
choco install vagrant
} else {
Write-Host "Vagrant already installed"
if ( -not (Test-Path 'C:\Program Files\Oracle\VirtualBox\VBoxManage.exe' -ErrorAction SilentlyContinue)) {
choco install virtualbox
choco install virtualbox.extensionpack
} else {
Write-Host "Virtualbox already installed"
Write-Host "Vagrant and friends installed, Installing required Vagrant plugins..."
vagrant plugin install vagrant-proxyconf vagrant-multi-hostsupdater vagrant-hostsupdater
Write-Host "Vagrant plugins complete. Pulling down 'talent-search-web' box and importing into Vagrant..."
vagrant box add MY_MACHINE_NAME file:////path\to\
Write-Host "Vagrant box downloaded."
Write-Host -ForegroundColor green "OK. If there were no exceptions above then you could open up a NEW powershell session and run a 'vagrant up' now!"

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@dragon788 dragon788 commented May 31, 2016

Surprised you don't use Boxstarter to do this yet as I see you have a repo for it. :)

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