diff --git a/images/win/Windows2016-Azure.json b/images/win/Windows2016-Azure.json
index 98d96feb95..5db5a4331a 100644
--- a/images/win/Windows2016-Azure.json
+++ b/images/win/Windows2016-Azure.json
@@ -217,10 +217,28 @@
                 "{{ template_dir }}/scripts/Installers/Install-ServiceFabricSDK.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Install-WSL.ps1"
+            ]
+        },
         {
             "type": "windows-restart",
             "restart_timeout": "30m"
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Install-UbuntuImage.ps1"
+            ]
+        },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Install-MSYS2.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
@@ -251,6 +269,18 @@
                 "{{ template_dir }}/scripts/Installers/Validate-ServiceFabricSDK.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Validate-WSL.ps1"
+            ]
+        },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Validate-MSYS2.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
diff --git a/images/win/Windows2019-Azure.json b/images/win/Windows2019-Azure.json
index 1b411672e3..9bda946be6 100644
--- a/images/win/Windows2019-Azure.json
+++ b/images/win/Windows2019-Azure.json
@@ -192,10 +192,28 @@
                 "{{ template_dir }}/scripts/Installers/Install-ServiceFabricSDK.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Install-WSL.ps1"
+            ]
+        },
         {
             "type": "windows-restart",
             "restart_timeout": "10m"
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Install-UbuntuImage.ps1"
+            ]
+        },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Install-MSYS2.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
@@ -220,6 +238,18 @@
                 "{{ template_dir }}/scripts/Installers/Validate-ServiceFabricSDK.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Validate-WSL.ps1"
+            ]
+        },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Validate-MSYS2.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
diff --git a/images/win/scripts/Installers/Install-MSYS2.ps1 b/images/win/scripts/Installers/Install-MSYS2.ps1
new file mode 100644
index 0000000000..8aa81034ba
--- /dev/null
+++ b/images/win/scripts/Installers/Install-MSYS2.ps1
@@ -0,0 +1,11 @@
+################################################################################
+##  File:  Install-MSYS2.ps1
+##  Desc:  Install MSYS2 via chocolaty
+################################################################################
+
+Import-Module -Name ImageHelpers
+
+$msys2Path = "C:\tools\msys64"
+choco install msys2 -y --params "/InstallDir:$msys2Path"
+
+Add-MachinePathItem $msys2Path
diff --git a/images/win/scripts/Installers/Install-UbuntuImage.ps1 b/images/win/scripts/Installers/Install-UbuntuImage.ps1
new file mode 100644
index 0000000000..ffa0d945a4
--- /dev/null
+++ b/images/win/scripts/Installers/Install-UbuntuImage.ps1
@@ -0,0 +1,33 @@
+################################################################################
+##  File:  Install-UbuntuImage.ps1
+##  Desc:  Install Ubuntu 18.04 Image for WSL
+################################################################################
+
+Import-Module -Name ImageHelpers
+
+$ubuntuTempDir = "$env:AGENT_TEMPDIRECTORY\ubuntu"
+
+if (-not (Test-Path $ubuntuTempDir)) {
+    New-Item -Path $ubuntuTempDir -ItemType Directory
+}
+
+Push-Location $ubuntuTempDir
+
+$ubuntuZipName = "ubuntu.zip"
+Invoke-WebRequest -Uri "https://aka.ms/wsl-ubuntu-1804" -OutFile $ubuntuZipName
+
+$ubuntuPath = "C:\tools\ubuntu"
+if (-not (Test-Path $ubuntuPath)) {
+    New-Item -Path $ubuntuPath -ItemType Directory
+}
+
+Expand-Archive -Path $ubuntuZipName -DestinationPath $ubuntuPath
+
+Add-MachinePathItem $ubuntuPath
+
+ubuntu1804 install --root
+ubuntu1804 run apt update
+ubuntu1804 run DEBIAN_FRONTEND=noninteractive apt upgrade -y
+
+Pop-Location
+Remove-Item $ubuntuTempDir -Recurse -Force
diff --git a/images/win/scripts/Installers/Install-WSL.ps1 b/images/win/scripts/Installers/Install-WSL.ps1
new file mode 100644
index 0000000000..bd255e81d0
--- /dev/null
+++ b/images/win/scripts/Installers/Install-WSL.ps1
@@ -0,0 +1,6 @@
+################################################################################
+##  File:  Install-WSL.ps1
+##  Desc:  Install Windows subsystem for Linux
+################################################################################
+
+Enable-WindowsOptionalFeature -Online -FeatureName Microsoft-Windows-Subsystem-Linux -NoRestart
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Validate-MSYS2.ps1 b/images/win/scripts/Installers/Validate-MSYS2.ps1
new file mode 100644
index 0000000000..957cc47d0c
--- /dev/null
+++ b/images/win/scripts/Installers/Validate-MSYS2.ps1
@@ -0,0 +1,14 @@
+################################################################################
+##  File:  Validate-MSYS2.ps1
+##  Desc:  Validate MSYS2 installation
+################################################################################
+
+$msysCommand = "msys2"
+
+Get-Command $msysCommand -ErrorAction SilentlyContinue -OutVariable commandInfo
+if ($commandInfo) {
+    Write-Host "$msysCommand is successfully installed"
+} else {
+    Write-Host "$msysCommand command unavailable"
+    exit 1
+}
diff --git a/images/win/scripts/Installers/Validate-WSL.ps1 b/images/win/scripts/Installers/Validate-WSL.ps1
new file mode 100644
index 0000000000..45ca376f6b
--- /dev/null
+++ b/images/win/scripts/Installers/Validate-WSL.ps1
@@ -0,0 +1,11 @@
+################################################################################
+##  File:  Validate-WSL.ps1
+##  Desc:  Validate Windows Subsystem for Linux installation
+################################################################################
+
+$FeatureInfo = (Get-WindowsOptionalFeature -Online | Where FeatureName -eq Microsoft-Windows-Subsystem-Linux)
+
+if ($FeatureInfo.State -eq "Disabled") {
+    Write-Host "Microsoft-Windows-Subsystem-Linux is Disabled"
+    exit 1
+}
\ No newline at end of file