diff --git a/Vagrantfile b/Vagrantfile
index 183888b1fd0d..68792c791a6d 100644
--- a/Vagrantfile
+++ b/Vagrantfile
@@ -1,20 +1,21 @@
 ### Documentation
-# This is a Vagrantfile for Beats development.
 #
-# Boxes
+# This is a Vagrantfile for Beats development and testing. These are unofficial
+# environments to help developers test things in different environments.
+#
+# Notes
 # =====
 #
-# win2012
-# -------
-# This box is used as a Windows development and testing environment for Beats.
+# win2012, win2016, win2019
+# -------------------------
+#
+# To login install Microsoft Remote Desktop Client (available in Mac App Store).
+# Then run 'vagrant rdp' and login as user/pass vagrant/vagrant. Or you can
+# manually configure your RDP client to connect to the mapped 3389 port as shown
+# by 'vagrant port win2019'.
 #
-# Usage and Features:
-#   - Two users exist: Administrator and Vagrant. Both have the password: vagrant
-#   - Use 'vagrant ssh' to open a Windows command prompt.
-#   - Use 'vagrant rdp' to open a Windows Remote Desktop session. Mac users must
-#     install the Microsoft Remote Desktop Client from the App Store.
-#   - There is a desktop shortcut labeled "Beats Shell" that opens a command prompt
-#     to C:\Gopath\src\github.com\elastic\beats where the code is mounted.
+# The provisioning currently does no install libpcap sources or a pcap driver
+# (like npcap) so Packetbeat will not build/run without some manually setup.
 #
 # solaris
 # -------------------
@@ -25,38 +26,93 @@
 #   - Use gmake instead of make.
 #   - Folder syncing doesn't work well. Consider copying the files into the box or
 #     cloning the project inside the box.
+###
 
+# Read the branch's Go version from the .go-version file.
 GO_VERSION = File.read(File.join(File.dirname(__FILE__), ".go-version")).strip
 
 # Provisioning for Windows PowerShell
 $winPsProvision = <<SCRIPT
-echo 'Creating github.com\elastic in the GOPATH'
-New-Item -itemtype directory -path "C:\\Gopath\\src\\github.com\\elastic" -force
-echo "Symlinking C:\\Vagrant to C:\\Gopath\\src\\github.com\\elastic"
-cmd /c mklink /d C:\\Gopath\\src\\github.com\\elastic\\beats \\\\vboxsvr\\vagrant
-
-echo "Installing gvm to manage go version"
-[Net.ServicePointManager]::SecurityProtocol = "tls12"
-Invoke-WebRequest -URI https://github.com/andrewkroh/gvm/releases/download/v0.1.0/gvm-windows-amd64.exe -Outfile C:\Windows\System32\gvm.exe
-C:\Windows\System32\gvm.exe --format=powershell #{GO_VERSION} | Invoke-Expression
-go version
-
-echo "Configure environment variables"
-[System.Environment]::SetEnvironmentVariable("GOROOT", "C:\\Users\\vagrant\\.gvm\\versions\\go#{GO_VERSION}.windows.amd64", [System.EnvironmentVariableTarget]::Machine)
-[System.Environment]::SetEnvironmentVariable("PATH", "$env:GOROOT\\bin;$env:PATH", [System.EnvironmentVariableTarget]::Machine)
-
-echo "Creating Beats Shell desktop shortcut"
-$WshShell = New-Object -comObject WScript.Shell
-$Shortcut = $WshShell.CreateShortcut("$Home\\Desktop\\Beats Shell.lnk")
-$Shortcut.TargetPath = "cmd.exe"
-$Shortcut.Arguments = '/c "SET GOROOT=C:\\Users\\vagrant\\.gvm\\versions\\go#{GO_VERSION}.windows.amd64&PATH=C:\\Users\\vagrant\\.gvm\\versions\\go#{GO_VERSION}.windows.amd64\\bin;%PATH%" && START'
-$Shortcut.WorkingDirectory = "C:\\Gopath\\src\\github.com\\elastic\\beats"
-$Shortcut.Save()
-
-echo "Disable automatic updates"
-$AUSettings = (New-Object -com "Microsoft.Update.AutoUpdate").Settings
-$AUSettings.NotificationLevel = 1
-$AUSettings.Save()
+$gopath_beats = "C:\\Gopath\\src\\github.com\\elastic\\beats"
+if (-Not (Test-Path $gopath_beats)) {
+    echo 'Creating github.com\\elastic in the GOPATH'
+    New-Item -itemtype directory -path "C:\\Gopath\\src\\github.com\\elastic" -force
+    echo "Symlinking C:\\Vagrant to C:\\Gopath\\src\\github.com\\elastic"
+    cmd /c mklink /d $gopath_beats \\\\vboxsvr\\vagrant
+}
+
+if (-Not (Get-Command "gvm" -ErrorAction SilentlyContinue)) {
+    echo "Installing gvm to manage go version"
+    [Net.ServicePointManager]::SecurityProtocol = "tls12"
+    Invoke-WebRequest -URI https://github.com/andrewkroh/gvm/releases/download/v0.2.1/gvm-windows-amd64.exe -Outfile C:\\Windows\\System32\\gvm.exe
+    C:\\Windows\\System32\\gvm.exe --format=powershell #{GO_VERSION} | Invoke-Expression
+    go version
+
+    echo "Configure Go environment variables"
+    [System.Environment]::SetEnvironmentVariable("GOPATH", "C:\\Gopath", [System.EnvironmentVariableTarget]::Machine)
+    [System.Environment]::SetEnvironmentVariable("GOROOT", "C:\\Users\\vagrant\\.gvm\\versions\\go#{GO_VERSION}.windows.amd64", [System.EnvironmentVariableTarget]::Machine)
+    [System.Environment]::SetEnvironmentVariable("PATH", "%GOROOT%\\bin;$env:PATH;C:\\Gopath\\bin", [System.EnvironmentVariableTarget]::Machine)
+}
+
+$shell_link = "$Home\\Desktop\\Beats Shell.lnk"
+if (-Not (Test-Path $shell_link)) {
+    echo "Creating Beats Shell desktop shortcut"
+    $WshShell = New-Object -comObject WScript.Shell
+    $Shortcut = $WshShell.CreateShortcut($shell_link)
+    $Shortcut.TargetPath = "powershell.exe"
+    $Shortcut.Arguments = "-noexit -command '$gopath_beats'"
+    $Shortcut.WorkingDirectory = $gopath_beats
+    $Shortcut.Save()
+}
+
+Try {
+    echo "Disabling automatic updates"
+    $AUSettings = (New-Object -com "Microsoft.Update.AutoUpdate").Settings
+    $AUSettings.NotificationLevel = 1
+    $AUSettings.Save()
+} Catch {
+    echo "Failed to disable automatic updates."
+}
+
+if (-Not (Get-Command "choco" -ErrorAction SilentlyContinue)) {
+    Set-ExecutionPolicy Bypass -Scope Process -Force
+    iex ((New-Object System.Net.WebClient).DownloadString('https://chocolatey.org/install.ps1'))
+}
+
+choco feature disable -n=showDownloadProgress
+
+if (-Not (Get-Command "python" -ErrorAction SilentlyContinue)) {
+    echo "Installing python2"
+    choco install python2 -y -r
+    refreshenv
+    $env:PATH = "$env:PATH;C:\\Python27;C:\\Python27\\Scripts"
+}
+
+if (-Not (Get-Command "pip" -ErrorAction SilentlyContinue)) {
+    echo "Installing pip"
+    Invoke-WebRequest https://bootstrap.pypa.io/get-pip.py -OutFile get-pip.py
+    python get-pip.py -U --force-reinstall 2>&1 | %{ "$_" }
+    rm get-pip.py
+    Invoke-WebRequest
+} else {
+    echo "Updating pip"
+    python -m pip install --upgrade pip 2>&1 | %{ "$_" }
+}
+
+if (-Not (Get-Command "virtualenv" -ErrorAction SilentlyContinue)) {
+    echo "Installing virtualenv"
+    python -m pip install virtualenv 2>&1 | %{ "$_" }
+}
+
+if (-Not (Get-Command "git" -ErrorAction SilentlyContinue)) {
+    echo "Installing git"
+    choco install git -y -r
+}
+
+if (-Not (Get-Command "gcc" -ErrorAction SilentlyContinue)) {
+    echo "Installing mingw (gcc)"
+    choco install mingw -y -r
+}
 SCRIPT
 
 # Provisioning for Unix/Linux
@@ -83,158 +139,148 @@ fi
 SCRIPT
 end
 
-Vagrant.configure(2) do |config|
+# Provision packages for Linux Debian.
+def linuxDebianProvision()
+  return <<SCRIPT
+#!/usr/bin/env bash
+set -eio pipefail
+apt-get update
+apt-get install -y make gcc python-pip python-virtualenv git
+SCRIPT
+end
 
+Vagrant.configure(2) do |config|
   # Windows Server 2012 R2
-  config.vm.define "win2012", primary: true do |win2012|
-
-    win2012.vm.box = "https://s3.amazonaws.com/beats-files/vagrant/beats-win2012-r2-virtualbox-2016-10-28_1224.box"
-    win2012.vm.guest = :windows
+  config.vm.define "win2012", primary: true do |c|
+    c.vm.box = "https://s3.amazonaws.com/beats-files/vagrant/beats-win2012-r2-virtualbox-2016-10-28_1224.box"
+    c.vm.guest = :windows
 
     # Communicator for windows boxes
-    win2012.vm.communicator = "winrm"
+    c.vm.communicator = "winrm"
 
     # Port forward WinRM and RDP
-    win2012.vm.network :forwarded_port, guest: 22,   host: 2222,  id: "ssh", auto_correct: true
-    win2012.vm.network :forwarded_port, guest: 3389, host: 33389, id: "rdp", auto_correct: true
-    win2012.vm.network :forwarded_port, guest: 5985, host: 55985, id: "winrm", auto_correct: true
+    c.vm.network :forwarded_port, guest: 22, host: 2222, id: "ssh", auto_correct: true
+    c.vm.network :forwarded_port, guest: 3389, host: 33389, id: "rdp", auto_correct: true
+    c.vm.network :forwarded_port, guest: 5985, host: 55985, id: "winrm", auto_correct: true
+
+    c.vm.provision "shell", inline: $winPsProvision
+  end
 
-    win2012.vm.provision "shell", inline: $winPsProvision
+  config.vm.define "win2016", primary: true do |c|
+    c.vm.box = "StefanScherer/windows_2016"
+    c.vm.provision "shell", inline: $winPsProvision, privileged: false
+  end
+
+  config.vm.define "win2019", primary: true do |c|
+    c.vm.box = "StefanScherer/windows_2019"
+    c.vm.provision "shell", inline: $winPsProvision, privileged: false
   end
 
   # Solaris 11.2
-  config.vm.define "solaris", primary: true do |solaris|
-    solaris.vm.box = "https://s3.amazonaws.com/beats-files/vagrant/beats-solaris-11.2-virtualbox-2016-11-02_1603.box"
-    solaris.vm.network :forwarded_port, guest: 22,   host: 2223,  id: "ssh", auto_correct: true
+  config.vm.define "solaris", primary: true do |c|
+    c.vm.box = "https://s3.amazonaws.com/beats-files/vagrant/beats-solaris-11.2-virtualbox-2016-11-02_1603.box"
+    c.vm.network :forwarded_port, guest: 22, host: 2223, id: "ssh", auto_correct: true
 
-    solaris.vm.provision "shell", inline: $unixProvision, privileged: false
+    c.vm.provision "shell", inline: $unixProvision, privileged: false
   end
 
   # FreeBSD 11.0
-  config.vm.define "freebsd", primary: true do |freebsd|
-    freebsd.vm.box = "https://s3.amazonaws.com/beats-files/vagrant/beats-freebsd-11.0-virtualbox-2016-11-02_1638.box"
-    freebsd.vm.network :forwarded_port, guest: 22,   host: 2224,  id: "ssh", auto_correct: true
+  config.vm.define "freebsd", primary: true do |c|
+    c.vm.box = "https://s3.amazonaws.com/beats-files/vagrant/beats-freebsd-11.0-virtualbox-2016-11-02_1638.box"
+    c.vm.network :forwarded_port, guest: 22, host: 2224, id: "ssh", auto_correct: true
 
     # Must use NFS to sync a folder on FreeBSD and this requires a host-only network.
     # To enable the /vagrant folder, set disabled to false and uncomment the private_network.
-    config.vm.synced_folder ".", "/vagrant", id: "vagrant-root", :nfs => true, disabled: true
-    #config.vm.network "private_network", ip: "192.168.135.18"
+    c.vm.synced_folder ".", "/vagrant", id: "vagrant-root", :nfs => true, disabled: true
+    #c.vm.network "private_network", ip: "192.168.135.18"
 
-    freebsd.vm.hostname = "beats-tester"
-    freebsd.vm.provision "shell", inline: $unixProvision, privileged: false
+    c.vm.hostname = "beats-tester"
+    c.vm.provision "shell", inline: $unixProvision, privileged: false
   end
 
   # OpenBSD 5.9-stable
-  config.vm.define "openbsd", primary: true do |openbsd|
-    openbsd.vm.box = "https://s3.amazonaws.com/beats-files/vagrant/beats-openbsd-5.9-current-virtualbox-2016-11-02_2007.box"
-    openbsd.vm.network :forwarded_port, guest: 22,   host: 2225,  id: "ssh", auto_correct: true
+  config.vm.define "openbsd", primary: true do |c|
+    c.vm.box = "https://s3.amazonaws.com/beats-files/vagrant/beats-openbsd-5.9-current-virtualbox-2016-11-02_2007.box"
+    c.vm.network :forwarded_port, guest: 22, host: 2225, id: "ssh", auto_correct: true
 
-    config.vm.synced_folder ".", "/vagrant", type: "rsync", disabled: true
-    config.vm.provider :virtualbox do |vbox|
+    c.vm.synced_folder ".", "/vagrant", type: "rsync", disabled: true
+    c.vm.provider :virtualbox do |vbox|
       vbox.check_guest_additions = false
       vbox.functional_vboxsf = false
     end
 
-    openbsd.vm.provision "shell", inline: $unixProvision, privileged: false
-  end
-
-  config.vm.define "precise64", primary: true do |c|
-    c.vm.box = "ubuntu/precise64"
-    c.vm.network :forwarded_port, guest: 22,   host: 2226,  id: "ssh", auto_correct: true
-
     c.vm.provision "shell", inline: $unixProvision, privileged: false
-    c.vm.provision "shell", inline: linuxGvmProvision, privileged: false
-
-    c.vm.synced_folder ".", "/vagrant", type: "virtualbox"
   end
 
   config.vm.define "precise32", primary: true do |c|
     c.vm.box = "ubuntu/precise32"
-    c.vm.network :forwarded_port, guest: 22,   host: 2226,  id: "ssh", auto_correct: true
+    c.vm.network :forwarded_port, guest: 22, host: 2226, id: "ssh", auto_correct: true
 
     c.vm.provision "shell", inline: $unixProvision, privileged: false
     c.vm.provision "shell", inline: linuxGvmProvision("386"), privileged: false
-
-    c.vm.synced_folder ".", "/vagrant", type: "virtualbox"
+    c.vm.provision "shell", inline: linuxDebianProvision
   end
 
-  config.vm.define "centos6", primary: true do |c|
-    c.vm.box = "bento/centos-6.9"
-    c.vm.network :forwarded_port, guest: 22,   host: 2229,  id: "ssh", auto_correct: true
+  config.vm.define "precise64", primary: true do |c|
+    c.vm.box = "ubuntu/precise64"
+    c.vm.network :forwarded_port, guest: 22, host: 2227, id: "ssh", auto_correct: true
 
     c.vm.provision "shell", inline: $unixProvision, privileged: false
     c.vm.provision "shell", inline: linuxGvmProvision, privileged: false
-    c.vm.provision "shell", inline: "yum install -y make gcc python-pip python-virtualenv git"
-
-    c.vm.synced_folder ".", "/vagrant", type: "virtualbox"
+    c.vm.provision "shell", inline: linuxDebianProvision
   end
 
-  config.vm.define "fedora27", primary: true do |c|
-    c.vm.box = "bento/fedora-27"
-    c.vm.network :forwarded_port, guest: 22,   host: 2227,  id: "ssh", auto_correct: true
+  config.vm.define "ubuntu1804", primary: true do |c|
+    c.vm.box = "ubuntu/bionic64"
+    c.vm.network :forwarded_port, guest: 22, host: 2228, id: "ssh", auto_correct: true
 
     c.vm.provision "shell", inline: $unixProvision, privileged: false
     c.vm.provision "shell", inline: linuxGvmProvision, privileged: false
-    c.vm.provision "shell", inline: "dnf install -y make gcc python-pip python-virtualenv git"
-
-    c.vm.synced_folder ".", "/vagrant", type: "virtualbox"
+    c.vm.provision "shell", inline: linuxDebianProvision
   end
 
-  config.vm.define "archlinux", primary: true do |c|
-    c.vm.box = "archlinux/archlinux"
-    c.vm.network :forwarded_port, guest: 22,   host: 2228,  id: "ssh", auto_correct: true
+  config.vm.define "centos6", primary: true do |c|
+    c.vm.box = "bento/centos-6.10"
+    c.vm.network :forwarded_port, guest: 22, host: 2229, id: "ssh", auto_correct: true
 
     c.vm.provision "shell", inline: $unixProvision, privileged: false
     c.vm.provision "shell", inline: linuxGvmProvision, privileged: false
-    c.vm.provision "shell", inline: "pacman -Sy && pacman -S --noconfirm make gcc python-pip python-virtualenv git"
-
-    c.vm.synced_folder ".", "/vagrant", type: "virtualbox"
+    c.vm.provision "shell", inline: "yum install -y make gcc python-pip python-virtualenv git rpm-devel"
   end
 
-  config.vm.define "ubuntu1804", primary: true do |c|
-    c.vm.box = "ubuntu/bionic64"
-    c.vm.network :forwarded_port, guest: 22,   host: 2229,  id: "ssh", auto_correct: true
+  config.vm.define "centos7", primary: true do |c|
+    c.vm.box = "bento/centos-7"
+    c.vm.network :forwarded_port, guest: 22, host: 2230, id: "ssh", auto_correct: true
 
     c.vm.provision "shell", inline: $unixProvision, privileged: false
     c.vm.provision "shell", inline: linuxGvmProvision, privileged: false
-    c.vm.provision "shell", inline: "apt-get update && apt-get install -y make gcc python-pip python-virtualenv git"
+    c.vm.provision "shell", inline: "yum install -y make gcc python-pip python-virtualenv git rpm-devel"
+  end
 
-    c.vm.synced_folder ".", "/vagrant", type: "virtualbox"
+  config.vm.define "fedora29", primary: true do |c|
+    c.vm.box = "bento/fedora-29"
+    c.vm.network :forwarded_port, guest: 22, host: 2231, id: "ssh", auto_correct: true
+
+    c.vm.provision "shell", inline: $unixProvision, privileged: false
+    c.vm.provision "shell", inline: linuxGvmProvision, privileged: false
+    c.vm.provision "shell", inline: "dnf install -y make gcc python-pip python-virtualenv git rpm-devel"
   end
 
   config.vm.define "sles12", primary: true do |c|
     c.vm.box = "elastic/sles-12-x86_64"
-    c.vm.network :forwarded_port, guest: 22,   host: 2230,  id: "ssh", auto_correct: true
+    c.vm.network :forwarded_port, guest: 22, host: 2232, id: "ssh", auto_correct: true
 
     c.vm.provision "shell", inline: $unixProvision, privileged: false
     c.vm.provision "shell", inline: linuxGvmProvision, privileged: false
     c.vm.provision "shell", inline: "pip install virtualenv"
-
-    c.vm.synced_folder ".", "/vagrant", type: "virtualbox"
   end
 
-  # Windows Server 2016
-  config.vm.define "win2016", primary: true do |machine|
-    machine.vm.box = "elastic/windows-2016-x86_64"
-    machine.vm.provision "shell", inline: $winPsProvision
-
-    machine.vm.provider "virtualbox" do |v|
-      v.memory = 4096
-    end
-  end
-
-  config.vm.define "centos7", primary: true do |c|
-    c.vm.box = "bento/centos-7"
-    c.vm.network :forwarded_port, guest: 22, host: 2231,  id: "ssh", auto_correct: true
+  config.vm.define "archlinux", primary: true do |c|
+    c.vm.box = "archlinux/archlinux"
+    c.vm.network :forwarded_port, guest: 22, host: 2233, id: "ssh", auto_correct: true
 
     c.vm.provision "shell", inline: $unixProvision, privileged: false
     c.vm.provision "shell", inline: linuxGvmProvision, privileged: false
-    c.vm.provision "shell", inline: "yum install -y make gcc python-pip python-virtualenv git"
-
-    c.vm.synced_folder ".", "/vagrant", type: "virtualbox"
+    c.vm.provision "shell", inline: "pacman -Sy && pacman -S --noconfirm make gcc python-pip python-virtualenv git"
   end
-
 end
-
-# -*- mode: ruby -*-
-# vi: set ft=ruby :