diff --git a/README.md b/README.md
index 5ccfdf2e..69b0c920 100644
--- a/README.md
+++ b/README.md
@@ -25,6 +25,11 @@ In general, these are the guidelines we consider when deciding what to pre-insta
 - Tools and versions will typically be removed 6 months after they are deprecated or have reached end-of-life.
 - If a tool can be installed during the build, we will evaluate how much time is saved
  and how much space is used by having the tool pre-installed.
+- MIT, Apache, and GNU licenses are ok, anything else we'll have to check with lawyers.
+- If a tool takes much space we will evaluate space usage and provide a decision if this tool can be pre-installed.
+- If a tool requires the support of more than one version, we will consider the cost of this maintenance, how often new versions bring dangerous updates.
+
+**Note:** For new tools, please, create an issue and get an approval from us to add this tool to the image before creating the pull request.
 
 ## Updates to virtual environments
 *Cadence*
diff --git a/images/linux/scripts/helpers/etc-environment.sh b/images/linux/scripts/helpers/etc-environment.sh
index 9637f242..24801723 100644
--- a/images/linux/scripts/helpers/etc-environment.sh
+++ b/images/linux/scripts/helpers/etc-environment.sh
@@ -26,7 +26,7 @@ function replaceEtcEnvironmentVariable {
     variable_value="$2"
 
     # modify /etc/environemnt in place by replacing a string that begins with variable_name
-    sudo sed -ie "s%^${variable_name}=.*$%${variable_name}=\"${variable_value}\"%" /etc/environment
+    sudo sed -i -e "s%^${variable_name}=.*$%${variable_name}=\"${variable_value}\"%" /etc/environment
 }
 
 function setEtcEnvironmentVariable {
diff --git a/images/linux/scripts/installers/1604/php.sh b/images/linux/scripts/installers/1604/php.sh
index 44f2ad3b..d2209041 100644
--- a/images/linux/scripts/installers/1604/php.sh
+++ b/images/linux/scripts/installers/1604/php.sh
@@ -283,6 +283,9 @@ prependEtcEnvironmentPath /home/runner/.config/composer/vendor/bin
 # Add composer bin folder to path
 echo 'export PATH="$PATH:$HOME/.config/composer/vendor/bin"' >> /etc/skel/.bashrc
 
+#Create composer folder for user to preserve folder permissions
+mkdir -p /etc/skel/.composer
+
 # Install phpunit (for PHP)
 wget -q -O phpunit https://phar.phpunit.de/phpunit-7.phar
 chmod +x phpunit
diff --git a/images/linux/scripts/installers/1604/preparemetadata.sh b/images/linux/scripts/installers/1604/preparemetadata.sh
index 45cfcabf..a26e1096 100644
--- a/images/linux/scripts/installers/1604/preparemetadata.sh
+++ b/images/linux/scripts/installers/1604/preparemetadata.sh
@@ -7,6 +7,7 @@
 
 source $HELPER_SCRIPTS/document.sh
 
+WriteItem "<!--- DO NOT EDIT - This markdown file is autogenerated. -->"
 AddTitle "$(lsb_release -ds)"
 WriteItem "The following software is installed on machines with the $IMAGE_VERSION update."
 WriteItem "***"
diff --git a/images/linux/scripts/installers/1804/basic.sh b/images/linux/scripts/installers/1804/basic.sh
index 29cb15b4..36a316f4 100644
--- a/images/linux/scripts/installers/1804/basic.sh
+++ b/images/linux/scripts/installers/1804/basic.sh
@@ -139,6 +139,10 @@ for cmd in curl file ftp jq netcat ssh parallel rsync shellcheck sudo telnet tim
     fi
 done
 
+# Workaround for systemd-resolve, since sometimes stub resolver does not work properly. Details: https://github.com/actions/virtual-environments/issues/798
+echo "Create resolv.conf link."
+ln -sf /run/systemd/resolve/resolv.conf /etc/resolv.conf
+
 # Document what was added to the image
 echo "Lastly, documenting what we added to the metadata file"
 DocumentInstalledItem "Basic CLI:"
diff --git a/images/linux/scripts/installers/1804/containers.sh b/images/linux/scripts/installers/1804/containers.sh
index 0ccf746a..547707e2 100644
--- a/images/linux/scripts/installers/1804/containers.sh
+++ b/images/linux/scripts/installers/1804/containers.sh
@@ -18,7 +18,9 @@ echo -e "[registries.search]\nregistries = ['docker.io', 'quay.io']" | tee /etc/
 
 ## Add version information to the metadata file
 echo "Documenting container tools version"
-PODMAN_VERSION='podman --version'
-BUILDAH_VERSION='buildah --version'
-SKOPEO_VERSION='skopeo --version'
-DocumentInstalledItem "Podman ($PODMAN_VERSION)\nBuildah ($BUILDAH_VERSION)\nSkopeo ($SKOPEO_VERSION)"
+PODMAN_VERSION="$(podman --version | cut -d " " -f 3)"
+BUILDAH_VERSION="$(buildah --version | cut -d " " -f 3)"
+SKOPEO_VERSION="$(skopeo --version | cut -d " " -f 3)"
+DocumentInstalledItem "Podman ($PODMAN_VERSION)"
+DocumentInstalledItem "Buildah ($BUILDAH_VERSION)"
+DocumentInstalledItem "Skopeo ($SKOPEO_VERSION)"
diff --git a/images/linux/scripts/installers/1804/php.sh b/images/linux/scripts/installers/1804/php.sh
index 8ab10d78..cbf25393 100644
--- a/images/linux/scripts/installers/1804/php.sh
+++ b/images/linux/scripts/installers/1804/php.sh
@@ -200,6 +200,9 @@ prependEtcEnvironmentPath /home/runner/.config/composer/vendor/bin
 # Add composer bin folder to path
 echo 'export PATH="$PATH:$HOME/.config/composer/vendor/bin"' >> /etc/skel/.bashrc
 
+#Create composer folder for user to preserve folder permissions
+mkdir -p /etc/skel/.composer
+
 # Install phpunit (for PHP)
 wget -q -O phpunit https://phar.phpunit.de/phpunit-7.phar
 chmod +x phpunit
diff --git a/images/linux/scripts/installers/1804/preparemetadata.sh b/images/linux/scripts/installers/1804/preparemetadata.sh
index 45cfcabf..e3304945 100644
--- a/images/linux/scripts/installers/1804/preparemetadata.sh
+++ b/images/linux/scripts/installers/1804/preparemetadata.sh
@@ -7,6 +7,7 @@
 
 source $HELPER_SCRIPTS/document.sh
 
+WriteItem "<!--- DO NOT EDIT - This markdown file is autogenerated. -->"
 AddTitle "$(lsb_release -ds)"
 WriteItem "The following software is installed on machines with the $IMAGE_VERSION update."
-WriteItem "***"
+WriteItem "***"
\ No newline at end of file
diff --git a/images/linux/scripts/installers/Install-Toolset.ps1 b/images/linux/scripts/installers/Install-Toolset.ps1
new file mode 100644
index 00000000..518a1f9b
--- /dev/null
+++ b/images/linux/scripts/installers/Install-Toolset.ps1
@@ -0,0 +1,55 @@
+################################################################################
+##  File:  Install-Toolset.ps1
+##  Team:  CI-Build
+##  Desc:  Install toolset
+################################################################################
+
+Function Install-Asset {
+    param(
+        [Parameter(Mandatory = $true)]
+        [object] $ReleaseAsset
+    )
+
+    Write-Host "Download $($ReleaseAsset.filename)"
+    wget $ReleaseAsset.download_url -nv --retry-connrefused --tries=10
+
+    Write-Host "Extract $($ReleaseAsset.filename) content..."
+    $assetFolderPath = Join-Path $env:INSTALLER_SCRIPT_FOLDER $($ReleaseAsset.filename)
+    New-Item -ItemType Directory -Path $assetFolderPath
+    tar -xzf $ReleaseAsset.filename -C $assetFolderPath
+
+    Write-Host "Invoke installation script..."
+    Push-Location -Path $assetFolderPath
+    Invoke-Expression "bash ./setup.sh"
+    Pop-Location
+}
+
+$ErrorActionPreference = "Stop"
+
+# Get toolset content
+$toolsetJson = Get-Content -Path "$env:INSTALLER_SCRIPT_FOLDER/toolset.json" -Raw
+$tools = ConvertFrom-Json -InputObject $toolsetJson | Select-Object -ExpandProperty toolcache
+
+foreach ($tool in $tools) {
+    # Get versions manifest for current tool
+    $assets = Invoke-RestMethod $tool.url
+
+    # Get github release asset for each version
+    foreach ($toolVersion in $tool.versions) {
+        $asset = $assets | Where-Object version -like $toolVersion `
+        | Select-Object -ExpandProperty files `
+        | Where-Object { ($_.platform -eq $tool.platform) -and ($_.platform_version -eq $tool.platform_version)} `
+        | Select-Object -First 1
+
+        Write-Host "Installing $($tool.name) $toolVersion $($tool.arch)..."
+        if ($asset -ne $null) {
+            Install-Asset -ReleaseAsset $asset
+        }
+        else {
+            Write-Host "Asset was not found in versions manifest"
+            exit 1
+        }
+    }
+}
+
+chown -R "$($env:SUDO_USER):$($env:SUDO_USER)" /opt/hostedtoolcache/Python
\ No newline at end of file
diff --git a/images/linux/scripts/installers/Validate-Toolset.ps1 b/images/linux/scripts/installers/Validate-Toolset.ps1
new file mode 100644
index 00000000..13847465
--- /dev/null
+++ b/images/linux/scripts/installers/Validate-Toolset.ps1
@@ -0,0 +1,62 @@
+################################################################################
+##  File:  Validate-Toolset.ps1
+##  Team:  CI-Build
+##  Desc:  Validate Toolset
+################################################################################
+
+function Run-ExecutableTests {
+    param (
+        [Parameter(Mandatory)] [string[]] $Executables,
+        [Parameter(Mandatory)] [string] $ToolPath
+    )
+
+    foreach ($executable in $Executables) {
+        $executablePath = Join-Path $ToolPath $executable
+
+        Write-Host "Check $executable..."
+        if (Test-Path $executablePath) {
+            Write-Host "$executable is successfully installed: $(& $executablePath --version)"
+        } else {
+            Write-Host "$executablePath is not installed!"
+            exit 1
+        }
+    }
+}
+
+$ErrorActionPreference = "Stop"
+
+# Define executables for cached tools
+$toolsExecutables = @{ Python = @("python", "bin/pip") }
+
+# Get toolset content
+$toolsetJson = Get-Content -Path "$env:INSTALLER_SCRIPT_FOLDER/toolset.json" -Raw
+$tools = ConvertFrom-Json -InputObject $toolsetJson | Select-Object -ExpandProperty toolcache
+
+foreach($tool in $tools) {
+    Invoke-Expression "bash -c `"source $env:HELPER_SCRIPTS/document.sh; DocumentInstalledItem '$($tool.name):'`""
+
+    $toolPath = Join-Path $env:AGENT_TOOLSDIRECTORY $tool.name
+    # Get executables for current tool
+    $toolExecs = $toolsExecutables[$tool.name]
+
+    foreach ($version in $tool.versions) {
+        # Check if version folder exists
+        $expectedVersionPath = Join-Path $toolPath $version
+        if (-not (Test-Path $expectedVersionPath)) {
+            Write-Host "Expected $($tool.name) $version folder is not found!"
+            exit 1
+        }
+
+        # Take latest installed version in case if toolset version contains wildcards
+        $foundVersion = Get-Item $expectedVersionPath `
+                        | Sort-Object -Property {[version]$_.name} -Descending `
+                        | Select-Object -First 1
+        $foundVersionPath = Join-Path $foundVersion $tool.arch
+
+        Write-Host "Run validation test for $($tool.name)($($tool.arch)) $($foundVersion.name) executables..."
+        Run-ExecutableTests -Executables $toolExecs -ToolPath $foundVersionPath
+
+        # Add tool version to documentation
+        Invoke-Expression "bash -c `"source $env:HELPER_SCRIPTS/document.sh; DocumentInstalledItemIndent '$($tool.name) $($foundVersion.name)'`""
+    }
+}
\ No newline at end of file
diff --git a/images/linux/scripts/installers/cmake.sh b/images/linux/scripts/installers/cmake.sh
index 340df3ee..0fd839a5 100644
--- a/images/linux/scripts/installers/cmake.sh
+++ b/images/linux/scripts/installers/cmake.sh
@@ -10,7 +10,7 @@ source $HELPER_SCRIPTS/document.sh
 # Test to see if the software in question is already installed, if not install it
 echo "Checking to see if the installer script has already been run"
 if command -v cmake; then
-    echo "Example variable already set to $EXAMPLE_VAR"
+    echo "cmake is already installed"
 else
 	curl -sL https://cmake.org/files/v3.17/cmake-3.17.0-Linux-x86_64.sh -o cmakeinstall.sh \
 	&& chmod +x cmakeinstall.sh \
diff --git a/images/linux/scripts/installers/hosted-tool-cache.sh b/images/linux/scripts/installers/hosted-tool-cache.sh
index f9e5b918..a0ff4466 100644
--- a/images/linux/scripts/installers/hosted-tool-cache.sh
+++ b/images/linux/scripts/installers/hosted-tool-cache.sh
@@ -49,12 +49,6 @@ done;
 
 popd
 
-DocumentInstalledItem "Python:"
-pythons=$(ls $AGENT_TOOLSDIRECTORY/Python)
-for python in $pythons; do
-	DocumentInstalledItemIndent "Python $python"
-done;
-
 DocumentInstalledItem "Ruby:"
 rubys=$(ls $AGENT_TOOLSDIRECTORY/Ruby)
 for ruby in $rubys; do
diff --git a/images/linux/scripts/installers/test-toolcache.sh b/images/linux/scripts/installers/test-toolcache.sh
index 2601db4b..53ed0715 100644
--- a/images/linux/scripts/installers/test-toolcache.sh
+++ b/images/linux/scripts/installers/test-toolcache.sh
@@ -69,6 +69,5 @@ done;
 
 AGENT_TOOLSDIRECTORY=/opt/hostedtoolcache
 
-Test_Hostedtoolcache_Tool "Python" "x64/python -c 'import sys;print(sys.version)'| head -1 | egrep -o '[0-9]+\.[0-9]+'"
 Test_Hostedtoolcache_Tool "Ruby" "x64/bin/ruby -e 'puts RUBY_VERSION' | egrep -o '[0-9]+\.[0-9]+'"
 Test_Hostedtoolcache_Tool "PyPy" "x64/bin/python -c 'import sys;print(sys.version)'| head -1 | egrep -o '[0-9]+\.[0-9]+' | cut -d '.' -f 1"
diff --git a/images/linux/scripts/installers/validate-disk-space.sh b/images/linux/scripts/installers/validate-disk-space.sh
new file mode 100644
index 00000000..5201848d
--- /dev/null
+++ b/images/linux/scripts/installers/validate-disk-space.sh
@@ -0,0 +1,14 @@
+#!/bin/bash
+################################################################################
+##  File:  validate-disk-space.sh
+##  Desc:  Validate free disk space
+################################################################################
+
+availableSpaceMB=$(df / -hm | sed 1d | awk '{ print $4}')
+minimumFreeSpaceMB=18000
+
+echo "Available disk space: $availableSpaceMB MB"
+if [ $availableSpaceMB -le $minimumFreeSpaceMB ]; then
+    echo "Not enough disk space on the image (minimum available space: $minimumFreeSpaceMB MB)"
+    exit 1
+fi
\ No newline at end of file
diff --git a/images/linux/toolcache-1604.json b/images/linux/toolcache-1604.json
index 40f4cd9d..96638f0f 100644
--- a/images/linux/toolcache-1604.json
+++ b/images/linux/toolcache-1604.json
@@ -1,7 +1,4 @@
 {
-    "@actions/toolcache-python-ubuntu-1604-x64": [
-        "2.7", "3.5", "3.6", "3.7", "3.8"
-    ],
     "@actions/toolcache-ruby-ubuntu-1604-x64": [
         "2.4", "2.5", "2.6", "2.7"
     ],
diff --git a/images/linux/toolcache-1804.json b/images/linux/toolcache-1804.json
index 26ad4d98..13c69785 100644
--- a/images/linux/toolcache-1804.json
+++ b/images/linux/toolcache-1804.json
@@ -1,7 +1,4 @@
 {
-    "@actions/toolcache-python-ubuntu-1804-x64": [
-        "2.7", "3.5", "3.6", "3.7", "3.8"
-    ],
     "@actions/toolcache-ruby-ubuntu-1804-x64": [
         "2.4", "2.5", "2.6", "2.7"
     ],
diff --git a/images/linux/toolset-1604.json b/images/linux/toolset-1604.json
new file mode 100644
index 00000000..e3953f81
--- /dev/null
+++ b/images/linux/toolset-1604.json
@@ -0,0 +1,18 @@
+{
+    "toolcache": [
+        {
+            "name": "Python",
+            "url" : "https://raw.githubusercontent.com/actions/python-versions/master/versions-manifest.json",
+            "platform" : "linux",
+            "platform_version": "16.04",
+            "arch": "x64",
+            "versions": [
+                "2.7.*",
+                "3.5.*",
+                "3.6.*",
+                "3.7.*",
+                "3.8.*"
+            ]
+        }
+    ]
+}
\ No newline at end of file
diff --git a/images/linux/toolset-1804.json b/images/linux/toolset-1804.json
new file mode 100644
index 00000000..a854ae6b
--- /dev/null
+++ b/images/linux/toolset-1804.json
@@ -0,0 +1,18 @@
+{
+    "toolcache": [
+        {
+            "name": "Python",
+            "url" : "https://raw.githubusercontent.com/actions/python-versions/master/versions-manifest.json",
+            "platform" : "linux",
+            "platform_version": "18.04",
+            "arch": "x64",
+            "versions": [
+                "2.7.*",
+                "3.5.*",
+                "3.6.*",
+                "3.7.*",
+                "3.8.*"
+            ]
+        }
+    ]
+}
\ No newline at end of file
diff --git a/images/linux/ubuntu1604.json b/images/linux/ubuntu1604.json
index 62081af5..a4f138db 100644
--- a/images/linux/ubuntu1604.json
+++ b/images/linux/ubuntu1604.json
@@ -269,6 +269,11 @@
             "source": "{{template_dir}}/toolcache-1604.json",
             "destination": "{{user `installer_script_folder`}}/toolcache.json"
         },
+        {
+            "type": "file",
+            "source": "{{template_dir}}/toolset-1604.json",
+            "destination": "{{user `installer_script_folder`}}/toolset.json"
+        },
         {
             "type": "shell",
             "scripts":[
@@ -287,6 +292,19 @@
             ],
             "execute_command": "sudo sh -c '{{ .Vars }} {{ .Path }}'"
         },
+        {
+            "type": "shell",
+            "scripts":[
+                "{{template_dir}}/scripts/installers/Install-Toolset.ps1",
+                "{{template_dir}}/scripts/installers/Validate-Toolset.ps1"
+            ],
+            "environment_vars": [
+                "METADATA_FILE={{user `metadata_file`}}",
+                "HELPER_SCRIPTS={{user `helper_script_folder`}}",
+                "INSTALLER_SCRIPT_FOLDER={{user `installer_script_folder`}}"
+            ],
+            "execute_command": "sudo sh -c '{{ .Vars }} pwsh -f {{ .Path }}'"
+        },
         {
             "type": "shell",
             "scripts":[
@@ -306,6 +324,12 @@
             ],
             "execute_command": "sudo sh -c '{{ .Vars }} {{ .Path }}'"
         },
+        {
+            "type": "shell",
+            "scripts":[
+                "{{template_dir}}/scripts/installers/validate-disk-space.sh"
+            ]
+        },
         {
             "type": "file",
             "source": "{{user `metadata_file`}}",
diff --git a/images/linux/ubuntu1804.json b/images/linux/ubuntu1804.json
index 41b75897..f72233e6 100644
--- a/images/linux/ubuntu1804.json
+++ b/images/linux/ubuntu1804.json
@@ -273,6 +273,11 @@
             "source": "{{template_dir}}/toolcache-1804.json",
             "destination": "{{user `installer_script_folder`}}/toolcache.json"
         },
+        {
+            "type": "file",
+            "source": "{{template_dir}}/toolset-1804.json",
+            "destination": "{{user `installer_script_folder`}}/toolset.json"
+        },
         {
             "type": "shell",
             "scripts":[
@@ -291,6 +296,19 @@
             ],
             "execute_command": "sudo sh -c '{{ .Vars }} {{ .Path }}'"
         },
+        {
+            "type": "shell",
+            "scripts":[
+                "{{template_dir}}/scripts/installers/Install-Toolset.ps1",
+                "{{template_dir}}/scripts/installers/Validate-Toolset.ps1"
+            ],
+            "environment_vars": [
+                "METADATA_FILE={{user `metadata_file`}}",
+                "HELPER_SCRIPTS={{user `helper_script_folder`}}",
+                "INSTALLER_SCRIPT_FOLDER={{user `installer_script_folder`}}"
+            ],
+            "execute_command": "sudo sh -c '{{ .Vars }} pwsh -f {{ .Path }}'"
+        },
         {
             "type": "shell",
             "scripts":[
@@ -310,6 +328,12 @@
             ],
             "execute_command": "sudo sh -c '{{ .Vars }} {{ .Path }}'"
         },
+        {
+            "type": "shell",
+            "scripts":[
+                "{{template_dir}}/scripts/installers/validate-disk-space.sh"
+            ]
+        },
         {
             "type": "file",
             "source": "{{user `metadata_file`}}",
diff --git a/images/macos/macos-10.15-Readme.md b/images/macos/macos-10.15-Readme.md
index 118cc7b6..e708126b 100644
--- a/images/macos/macos-10.15-Readme.md
+++ b/images/macos/macos-10.15-Readme.md
@@ -1,10 +1,8 @@
-# macOS Catalina 10.15.4 (19E266)
-The following software is installed on machines with the 20200328.1 update.
-
-#### Xcode 11.3.1 set by default
-## Operating System
-
-- OS X 10.15.4 (19E287) **Catalina**
+# OS X info
+- System Version: macOS 10.15.4 (19E287)
+- Kernel Version: Darwin 19.4.0
+- System Integrity Protection: Enabled
+- Image Version: 20200425.1
 
 # Installed Software
 ## Language and Runtime
@@ -14,7 +12,7 @@ The following software is installed on machines with the 20200328.1 update.
 - Java 12: Zulu12.3+11-CA (build 12.0.2+3)
 - Java 13: Zulu13.31+11-CA (build 13.0.3+3-MTS)
 - Java 14: Zulu14.28+21-CA (build 14.0.1+8)
-- Rust 1.42.0
+- Rust 1.43.0
 - Clang/LLVM 10.0.0
 - gcc-8 (Homebrew GCC 8.4.0_1) 8.4.0
 - gcc-9 (Homebrew GCC 9.3.0_1) 9.3.0
@@ -22,7 +20,7 @@ The following software is installed on machines with the 20200328.1 update.
 - GNU Fortran (Homebrew GCC 9.3.0_1) 9.3.0
 - Node.js v12.16.2
 - NVM 0.33.11
-- NVM - Cached node versions: v6.17.1 v8.17.0 v10.20.0 v12.16.2 v13.13.0
+- NVM - Cached node versions: v6.17.1 v8.17.0 v10.20.1 v12.16.2 v13.13.0
 - PowerShell 7.0.0
 - Python 2.7.17
 - Python 3.7.7
@@ -53,43 +51,43 @@ The following software is installed on machines with the 20200328.1 update.
 
 ## Utilities
 - Curl 7.69.1
-- Git: 2.26.1
+- Git: 2.26.2
 - Git LFS: 2.10.0
 - Hub CLI: 2.14.2
 - GNU Wget 1.20.3
 - Subversion (SVN) 1.13.0
 - Packer 1.5.5
-- GNU parallel 20200322
+- GNU parallel 20200422
 - OpenSSL 1.0.2t  10 Sep 2019
 - jq 1.6
 - gpg (GnuPG) 2.2.20
 - psql (PostgreSQL) 12.2
 - PostgreSQL 12.2
 - aria2 1.35.0
-- azcopy 10.4.0
+- azcopy 10.4.1
 - zstd 1.4.4
-- bazel 3.0.0
+- bazel 3.1.0
 - bazelisk v1.4.0
-- helm v3.1.2+gd878d4d
+- helm v3.2.0+ge11b7ce
 - virtualbox 6.1.6r137129
 - Vagrant 2.2.7
 
 ## Tools
-- Fastlane 2.145.0
+- Fastlane 2.146.1
 - Cmake 3.17.1
-- App Center CLI 2.4.1
-- Azure CLI 2.3.1
-- AWS CLI 2.0.8
+- App Center CLI 2.5.0
+- Azure CLI 2.4.0
+- AWS CLI 2.0.9
 - AWS SAM CLI 0.47.0
-- Aliyun CLI 3.0.37
+- Aliyun CLI 3.0.39
 
 ## Browsers
 - Safari 13.1 (15609.1.20.111.8)
 - SafariDriver 13.1 (15609.1.20.111.8)
-- Google Chrome 81.0.4044.113
+- Google Chrome 81.0.4044.122
 - ChromeDriver 81.0.4044.69
-- Microsoft Edge 81.0.416.53
-- MSEdgeDriver 81.0.416.58
+- Microsoft Edge 81.0.416.64
+- MSEdgeDriver 81.0.416.64
 - Mozilla Firefox 75.0
 - geckodriver 0.26.0
 
@@ -113,7 +111,7 @@ The following software is installed on machines with the 20200328.1 update.
 
 ## Xamarin
 ### Visual Studio for Mac
-- 8.5.3.16
+- 8.5.4.12
 
 ### Mono
 - 6.8.0.123
@@ -149,14 +147,15 @@ The following software is installed on machines with the 20200328.1 update.
 ## Xcode
 | Version          | Build   | Path                           |
 | ---------------- | ------- | ------------------------------ |
-| 11.4.1           | 11E503a | /Applications/Xcode_11.4.1.app |
+| 11.4.1 (default) | 11E503a | /Applications/Xcode_11.4.1.app |
 | 11.4             | 11E146  | /Applications/Xcode_11.4.app   |
-| 11.3.1 (default) | 11C505  | /Applications/Xcode_11.3.1.app |
+| 11.3.1           | 11C505  | /Applications/Xcode_11.3.1.app |
 | 11.3             | 11C29   | /Applications/Xcode_11.3.app   |
 | 11.2.1           | 11B500  | /Applications/Xcode_11.2.1.app |
 | 11.2             | 11B52   | /Applications/Xcode_11.2.app   |
 | 11.1             | 11A1027 | /Applications/Xcode_11.1.app   |
 | 11.0             | 11A420a | /Applications/Xcode_11.app     |
+| 10.3             | 10G8    | /Applications/Xcode_10.3.app   |
 
 ### Xcode Support Tools
 - Nomad CLI 3.1.2
@@ -168,44 +167,54 @@ The following software is installed on machines with the 20200328.1 update.
 ### Installed SDKs
 | SDK                     | SDK Name             | Xcode Version                                        |
 | ----------------------- | -------------------- | ---------------------------------------------------- |
+| macOS 10.14             | macosx10.14          | 10.3                                                 |
 | macOS 10.15             | macosx10.15          | 11.0, 11.1, 11.2, 11.2.1, 11.3, 11.3.1, 11.4, 11.4.1 |
+| iOS 12.4                | iphoneos12.4         | 10.3                                                 |
 | iOS 13.0                | iphoneos13.0         | 11.0                                                 |
 | iOS 13.1                | iphoneos13.1         | 11.1                                                 |
 | iOS 13.2                | iphoneos13.2         | 11.2, 11.2.1, 11.3, 11.3.1                           |
 | iOS 13.4                | iphoneos13.4         | 11.4, 11.4.1                                         |
+| Simulator - iOS 12.4    | iphonesimulator12.4  | 10.3                                                 |
 | Simulator - iOS 13.0    | iphonesimulator13.0  | 11.0                                                 |
 | Simulator - iOS 13.1    | iphonesimulator13.1  | 11.1                                                 |
 | Simulator - iOS 13.2    | iphonesimulator13.2  | 11.2, 11.2.1, 11.3, 11.3.1                           |
 | Simulator - iOS 13.4    | iphonesimulator13.4  | 11.4, 11.4.1                                         |
+| tvOS 12.4               | appletvos12.4        | 10.3                                                 |
 | tvOS 13.0               | appletvos13.0        | 11.0, 11.1                                           |
 | tvOS 13.2               | appletvos13.2        | 11.2, 11.2.1, 11.3, 11.3.1                           |
 | tvOS 13.4               | appletvos13.4        | 11.4, 11.4.1                                         |
+| Simulator - tvOS 12.4   | appletvsimulator12.4 | 10.3                                                 |
 | Simulator - tvOS 13.0   | appletvsimulator13.0 | 11.0, 11.1                                           |
 | Simulator - tvOS 13.2   | appletvsimulator13.2 | 11.2, 11.2.1, 11.3, 11.3.1                           |
 | Simulator - tvOS 13.4   | appletvsimulator13.4 | 11.4, 11.4.1                                         |
+| watchOS 5.3             | watchos5.3           | 10.3                                                 |
 | watchOS 6.0             | watchos6.0           | 11.0, 11.1                                           |
 | watchOS 6.1             | watchos6.1           | 11.2, 11.2.1, 11.3, 11.3.1                           |
 | watchOS 6.2             | watchos6.2           | 11.4, 11.4.1                                         |
+| Simulator - watchOS 5.3 | watchsimulator5.3    | 10.3                                                 |
 | Simulator - watchOS 6.0 | watchsimulator6.0    | 11.0, 11.1                                           |
 | Simulator - watchOS 6.1 | watchsimulator6.1    | 11.2, 11.2.1, 11.3, 11.3.1                           |
 | Simulator - watchOS 6.2 | watchsimulator6.2    | 11.4, 11.4.1                                         |
 | DriverKit 19.0          | driverkit.macosx19.0 | 11.0, 11.1, 11.2, 11.2.1, 11.3, 11.3.1, 11.4, 11.4.1 |
 
 ### Installed Simulators
-| OS          | Xcode Version                    | Simulators                                                                                                                                                                                                                                                              |
-| ----------- | -------------------------------- | ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
-| iOS 13.0    | 11.0                             | iPhone 8<br>iPhone 8 Plus<br>iPhone 11<br>iPhone 11 Pro<br>iPhone 11 Pro Max<br>iPad Pro (9.7-inch)<br>iPad Pro (11-inch)<br>iPad Pro (12.9-inch) (3rd generation)<br>iPad Air (3rd generation)                                                                         |
-| iOS 13.1    | 11.1                             | iPhone 8<br>iPhone 8 Plus<br>iPhone 11<br>iPhone 11 Pro<br>iPhone 11 Pro Max<br>iPad Pro (9.7-inch)<br>iPad Pro (11-inch)<br>iPad Pro (12.9-inch) (3rd generation)<br>iPad Air (3rd generation)                                                                         |
-| iOS 13.2    | 11.2<br>11.2.1                   | iPhone 8<br>iPhone 8 Plus<br>iPhone 11<br>iPhone 11 Pro<br>iPhone 11 Pro Max<br>iPad Pro (9.7-inch)<br>iPad Pro (11-inch)<br>iPad Pro (12.9-inch) (3rd generation)<br>iPad Air (3rd generation)                                                                         |
-| iOS 13.3    | 11.3<br>11.3.1                   | iPhone 8<br>iPhone 8 Plus<br>iPhone 11<br>iPhone 11 Pro<br>iPhone 11 Pro Max<br>iPad Pro (9.7-inch)<br>iPad (7th generation)<br>iPad Pro (11-inch)<br>iPad Pro (12.9-inch) (3rd generation)<br>iPad Air (3rd generation)                                                |
-| iOS 13.4    | 11.4<br>11.4.1                   | iPhone 8<br>iPhone 8 Plus<br>iPhone 11<br>iPhone 11 Pro<br>iPhone 11 Pro Max<br>iPad Pro (9.7-inch)<br>iPad (7th generation)<br>iPad Pro (11-inch) (2nd generation)<br>iPad Pro (12.9-inch) (4th generation)<br>iPad Air (3rd generation)<br>iPhone SE (2nd generation) |
-| tvOS 13.0   | 11.0<br>11.1                     | Apple TV<br>Apple TV 4K<br>Apple TV 4K (at 1080p)                                                                                                                                                                                                                       |
-| tvOS 13.2   | 11.2<br>11.2.1                   | Apple TV<br>Apple TV 4K<br>Apple TV 4K (at 1080p)                                                                                                                                                                                                                       |
-| tvOS 13.3   | 11.3<br>11.3.1                   | Apple TV<br>Apple TV 4K<br>Apple TV 4K (at 1080p)                                                                                                                                                                                                                       |
-| tvOS 13.4   | 11.4<br>11.4.1                   | Apple TV<br>Apple TV 4K<br>Apple TV 4K (at 1080p)                                                                                                                                                                                                                       |
-| watchOS 6.0 | 11.0<br>11.1                     | Apple Watch Series 4 - 40mm<br>Apple Watch Series 4 - 44mm<br>Apple Watch Series 5 - 40mm<br>Apple Watch Series 5 - 44mm                                                                                                                                                |
-| watchOS 6.1 | 11.2<br>11.2.1<br>11.3<br>11.3.1 | Apple Watch Series 4 - 40mm<br>Apple Watch Series 4 - 44mm<br>Apple Watch Series 5 - 40mm<br>Apple Watch Series 5 - 44mm                                                                                                                                                |
-| watchOS 6.2 | 11.4<br>11.4.1                   | Apple Watch Series 4 - 40mm<br>Apple Watch Series 4 - 44mm<br>Apple Watch Series 5 - 40mm<br>Apple Watch Series 5 - 44mm                                                                                                                                                |
+| OS          | Xcode Version                    | Simulators                                                                                                                                                                                                                                                                                                                                                                                                                                                                                  |
+| ----------- | -------------------------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
+| iOS 12.4    | 10.3                             | iPhone 5s<br>iPhone 6 Plus<br>iPhone 6<br>iPhone 6s<br>iPhone 6s Plus<br>iPhone SE<br>iPhone 7<br>iPhone 7 Plus<br>iPhone 8<br>iPhone 8 Plus<br>iPhone X<br>iPhone Xs<br>iPhone Xs Max<br>iPhone Xʀ<br>iPad Air<br>iPad Air 2<br>iPad Pro (9.7-inch)<br>iPad Pro (12.9-inch)<br>iPad (5th generation)<br>iPad Pro (12.9-inch) (2nd generation)<br>iPad Pro (10.5-inch)<br>iPad (6th generation)<br>iPad Pro (11-inch)<br>iPad Pro (12.9-inch) (3rd generation)<br>iPad Air (3rd generation) |
+| iOS 13.0    | 11.0                             | iPhone 8<br>iPhone 8 Plus<br>iPhone 11<br>iPhone 11 Pro<br>iPhone 11 Pro Max<br>iPad Pro (9.7-inch)<br>iPad Pro (11-inch)<br>iPad Pro (12.9-inch) (3rd generation)<br>iPad Air (3rd generation)                                                                                                                                                                                                                                                                                             |
+| iOS 13.1    | 11.1                             | iPhone 8<br>iPhone 8 Plus<br>iPhone 11<br>iPhone 11 Pro<br>iPhone 11 Pro Max<br>iPad Pro (9.7-inch)<br>iPad Pro (11-inch)<br>iPad Pro (12.9-inch) (3rd generation)<br>iPad Air (3rd generation)                                                                                                                                                                                                                                                                                             |
+| iOS 13.2    | 11.2<br>11.2.1                   | iPhone 8<br>iPhone 8 Plus<br>iPhone 11<br>iPhone 11 Pro<br>iPhone 11 Pro Max<br>iPad Pro (9.7-inch)<br>iPad Pro (11-inch)<br>iPad Pro (12.9-inch) (3rd generation)<br>iPad Air (3rd generation)                                                                                                                                                                                                                                                                                             |
+| iOS 13.3    | 11.3<br>11.3.1                   | iPhone 8<br>iPhone 8 Plus<br>iPhone 11<br>iPhone 11 Pro<br>iPhone 11 Pro Max<br>iPad Pro (9.7-inch)<br>iPad Pro (11-inch)<br>iPad Pro (12.9-inch) (3rd generation)<br>iPad Air (3rd generation)                                                                                                                                                                                                                                                                                             |
+| iOS 13.4    | 11.4<br>11.4.1                   | iPhone 8<br>iPhone 8 Plus<br>iPhone 11<br>iPhone 11 Pro<br>iPhone 11 Pro Max<br>iPad Pro (9.7-inch)<br>iPad (7th generation)<br>iPad Pro (11-inch) (2nd generation)<br>iPad Pro (12.9-inch) (4th generation)<br>iPad Air (3rd generation)<br>iPhone SE (2nd generation)                                                                                                                                                                                                                     |
+| tvOS 12.4   | 10.3                             | Apple TV<br>Apple TV 4K<br>Apple TV 4K (at 1080p)                                                                                                                                                                                                                                                                                                                                                                                                                                           |
+| tvOS 13.0   | 11.0<br>11.1                     | Apple TV<br>Apple TV 4K<br>Apple TV 4K (at 1080p)                                                                                                                                                                                                                                                                                                                                                                                                                                           |
+| tvOS 13.2   | 11.2<br>11.2.1                   | Apple TV<br>Apple TV 4K<br>Apple TV 4K (at 1080p)                                                                                                                                                                                                                                                                                                                                                                                                                                           |
+| tvOS 13.3   | 11.3<br>11.3.1                   | Apple TV<br>Apple TV 4K<br>Apple TV 4K (at 1080p)                                                                                                                                                                                                                                                                                                                                                                                                                                           |
+| tvOS 13.4   | 11.4<br>11.4.1                   | Apple TV<br>Apple TV 4K<br>Apple TV 4K (at 1080p)                                                                                                                                                                                                                                                                                                                                                                                                                                           |
+| watchOS 5.3 | 10.3                             | Apple Watch Series 2 - 38mm<br>Apple Watch Series 2 - 42mm<br>Apple Watch Series 3 - 38mm<br>Apple Watch Series 3 - 42mm<br>Apple Watch Series 4 - 40mm<br>Apple Watch Series 4 - 44mm                                                                                                                                                                                                                                                                                                      |
+| watchOS 6.0 | 11.0<br>11.1                     | Apple Watch Series 4 - 40mm<br>Apple Watch Series 4 - 44mm<br>Apple Watch Series 5 - 40mm<br>Apple Watch Series 5 - 44mm                                                                                                                                                                                                                                                                                                                                                                    |
+| watchOS 6.1 | 11.2<br>11.2.1<br>11.3<br>11.3.1 | Apple Watch Series 4 - 40mm<br>Apple Watch Series 4 - 44mm<br>Apple Watch Series 5 - 40mm<br>Apple Watch Series 5 - 44mm                                                                                                                                                                                                                                                                                                                                                                    |
+| watchOS 6.2 | 11.4<br>11.4.1                   | Apple Watch Series 4 - 40mm<br>Apple Watch Series 4 - 44mm<br>Apple Watch Series 5 - 40mm<br>Apple Watch Series 5 - 44mm                                                                                                                                                                                                                                                                                                                                                                    |
 
 ## Android
 ### Android SDK Tools
@@ -216,7 +225,7 @@ The following software is installed on machines with the 20200328.1 update.
 ### Android SDK Platform-Tools
 | Package Name   | Description                                 |
 | -------------- | ------------------------------------------- |
-| platform-tools | Android SDK Platform-Tools, Revision 29.0.6 |
+| platform-tools | Android SDK Platform-Tools, Revision 30.0.0 |
 
 ### Android SDK Platforms
 | Package Name | Description                         |
@@ -262,7 +271,7 @@ The following software is installed on machines with the 20200328.1 update.
 | ---------------- | ------------ |
 | cmake            | 3.6.4111459  |
 | lldb             | 3.1.4508709  |
-| ndk-bundle       | 21.0.6113669 |
+| ndk-bundle       | 21.1.6352462 |
 | Android Emulator | 30.0.5       |
 
 ### Android Google APIs
@@ -280,3 +289,5 @@ The following software is installed on machines with the 20200328.1 update.
 | Google Play services                            | 49      |
 | Google Repository                               | 58      |
 | Intel x86 Emulator Accelerator (HAXM installer) | 7.5.1   |
+
+
diff --git a/images/win/Windows2016-Azure.json b/images/win/Windows2016-Azure.json
index 55a1e611..834de3af 100644
--- a/images/win/Windows2016-Azure.json
+++ b/images/win/Windows2016-Azure.json
@@ -18,6 +18,7 @@
         "run_scan_antivirus": "false",
 
         "root_folder": "C:",
+        "toolset_json_path": "{{env `TEMP`}}\\toolset.json",
         "image_folder": "C:\\image",
         "commit_file": "C:\\image\\commit.txt",
         "imagedata_file": "C:\\imagedata.json",
@@ -318,6 +319,11 @@
             "source": "{{template_dir}}/toolcache-2016.json",
             "destination": "{{user `root_folder`}}/toolcache.json"
         },
+        {
+            "type": "file",
+            "source": "{{template_dir}}/toolset-2016.json",
+            "destination": "{{user `toolset_json_path`}}"
+        },
         {
             "type": "powershell",
             "environment_vars":[
@@ -328,6 +334,15 @@
                 "{{ template_dir }}/scripts/Installers/Download-ToolCache.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "environment_vars":[
+                "TOOLSET_JSON_PATH={{user `toolset_json_path`}}"
+            ],
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Install-Toolset.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
@@ -642,6 +657,15 @@
                 "{{ template_dir }}/scripts/Installers/Validate-ToolCache.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "environment_vars":[
+                "TOOLSET_JSON_PATH={{user `toolset_json_path`}}"
+            ],
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Validate-Toolset.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
@@ -883,6 +907,12 @@
                 "{{ template_dir }}/scripts/Installers/Validate-Kind.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Validate-DiskSpace.ps1"
+            ]
+        },
         {
             "type": "file",
             "source": "C:\\InstalledSoftware.md",
diff --git a/images/win/Windows2016-Readme.md b/images/win/Windows2016-Readme.md
index 7c522462..36540bef 100644
--- a/images/win/Windows2016-Readme.md
+++ b/images/win/Windows2016-Readme.md
@@ -1,6 +1,6 @@
 # Windows Server 2016
 
-The following software is installed on machines with the 20200416.1 update.
+The following software is installed on machines with the 20200426.1 update.
 
 Components marked with **\*** have been upgraded since the previous version of the image.
 
@@ -25,7 +25,7 @@ _Environment:_
 
 ## Helm
 
-_Version:_ v3.1.2+gd878d4d<br/>
+_Version:_ v3.2.0+ge11b7ce<br/>
 _Environment:_
 * PATH: contains location of helm
 
@@ -168,8 +168,8 @@ _WDK Visual Studio Extension Version:_ 10.0.17740.0<br/>
 
 ## Azure Service Fabric
 
-_SDK Version:_ 4.0.470.9590<br/>
-_Runtime Version:_ 7.0.470.9590
+_SDK Version:_ 4.1.409.9590<br/>
+_Runtime Version:_ 7.1.409.9590
 
 ## WinAppDriver
 
@@ -177,7 +177,7 @@ _Version:_ 1.1.1809.18001<br/>
 
 ## AWS CLI
 
-_Version:_ aws-cli 2.0.7<br/>
+_Version:_ aws-cli 2.0.9<br/>
 
 ## Android SDK Build Tools
 
@@ -428,10 +428,14 @@ _Description:_ .NET has been configured to use TLS 1.2 by default
 
 ## Azure CLI
 
-_Version:_ 2.3.1
+_Version:_ 2.4.0
 _Environment:_
 * PATH: contains location of az.cmd
 
+## AWS SAM CLI
+
+_Version:_ 0.47.0<br/>
+
 ## Azure DevOps Cli extension
 
 _Version:_ azure-devops                      0.18.0
@@ -446,7 +450,7 @@ _Version:_ 2.7.13 (x86)<br/>_Version:_ 3.6.9 (x86)<br/>
 
 ## Ruby
 
-_Version:_ 2.4.10 (x64)<br/>_Version:_ 2.5.8 (x64)<br/>_Version:_ 2.6.6 (x64)<br/>_Version:_ 2.7.1 (x64)<br/><br/>__System default version:__ Ruby 2.5.8p224<br/>_Environment:_<br/>* Location: C:\hostedtoolcache\windows\Ruby\2.5.8\x64\bin<br/>* PATH: contains the location of Ruby 2.5.8p224<br/>* Gem Version: 2.7.6.2<br/>
+_Version:_ 2.4.10 (x64)<br/>_Version:_ 2.5.8 (x64)<br/>_Version:_ 2.6.6 (x64)<br/>_Version:_ 2.7.1 (x64)<br/><br/>__System default version:__ Ruby 2.5.8p224<br/>_Environment:_<br/>* Location: C:\hostedtoolcache\windows\Ruby\2.5.8\x64\bin<br/>* PATH: contains the location of Ruby 2.5.8p224<br/>* Gem Version: 3.1.2<br/>
 
 ## OpenSSL
 
@@ -458,7 +462,7 @@ _Version:_ v5.30.2<br/>
 
 ## Git
 
-_Version:_ 2.26.1<br/>
+_Version:_ 2.26.2<br/>
 _Environment:_
 * PATH: contains location of git.exe
 
@@ -522,14 +526,14 @@ _Environment:_
 
 ## Rust (64-bit)
 
-#### 1.42.0
+#### 1.43.0
 _Location:_ C:\Rust\.cargo\bin
 _Environment:_
 * PATH: contains the location of rustc.exe
 
 ## Julia (x64)
 
-_Version:_ 1.4.0<br/>
+_Version:_ 1.4.1<br/>
 
 ## sbt
 
@@ -544,12 +548,12 @@ _Environment:_
 ## Google Chrome
 
 _version:_
-81.0.4044.113
+81.0.4044.122
 
 ## Microsoft Edge
 
 _version:_
-81.0.416.53
+81.0.416.64
 
 ## Mozilla Firefox
 
@@ -586,7 +590,7 @@ _Environment:_
 #### Microsoft Edge Driver
 
 _version:_
-81.0.416.53
+81.0.416.64
 
 _Environment:_
 * EdgeWebDriver: location of msedgedriver.exe
@@ -611,11 +615,11 @@ _Environment:_
 
 ## bazel
 
-_Version:_ bazel 3.0.0<br/>
+_Version:_ bazel 3.1.0<br/>
 
 ## bazelisk
 
-_Version:_ 1.3.0<br/>
+_Version:_ 1.4.0<br/>
 
 ## Alibaba Cloud CLI
 
@@ -678,7 +682,9 @@ _Environment:_
 
 _SDK:_
 * 3.1.201 C:\Program Files\dotnet\sdk\3.1.201
+* 3.1.200 C:\Program Files\dotnet\sdk\3.1.200
 * 3.1.103 C:\Program Files\dotnet\sdk\3.1.103
+* 3.1.102 C:\Program Files\dotnet\sdk\3.1.102
 * 3.1.101 C:\Program Files\dotnet\sdk\3.1.101
 * 3.1.100 C:\Program Files\dotnet\sdk\3.1.100
 * 2.2.402 C:\Program Files\dotnet\sdk\2.2.402
@@ -742,6 +748,7 @@ _SDK:_
 
 _Runtime:_
 * 3.1.3 C:\Program Files\dotnet\shared\Microsoft.NETCore.App\3.1.3
+* 3.1.2 C:\Program Files\dotnet\shared\Microsoft.NETCore.App\3.1.2
 * 3.1.1 C:\Program Files\dotnet\shared\Microsoft.NETCore.App\3.1.1
 * 3.1.0 C:\Program Files\dotnet\shared\Microsoft.NETCore.App\3.1.0
 * 2.2.8 C:\Program Files\dotnet\shared\Microsoft.NETCore.App\2.2.8
@@ -855,7 +862,7 @@ _Environment:_
 
 ## Kubectl
 
-_Version:_ Client Version: v1.18.1<br/>
+_Version:_ Client Version: v1.18.2<br/>
 _Environment:_
 * PATH: contains location of kubectl.exe
 
diff --git a/images/win/Windows2019-Azure.json b/images/win/Windows2019-Azure.json
index ab28c810..1b3e5f74 100644
--- a/images/win/Windows2019-Azure.json
+++ b/images/win/Windows2019-Azure.json
@@ -18,6 +18,7 @@
         "run_scan_antivirus": "false",
 
         "root_folder": "C:",
+        "toolset_json_path": "{{env `TEMP`}}\\toolset.json",
         "image_folder": "C:\\image",
         "commit_file": "C:\\image\\commit.txt",
         "imagedata_file": "C:\\imagedata.json",
@@ -291,6 +292,11 @@
             "source": "{{template_dir}}/toolcache-2019.json",
             "destination": "{{user `root_folder`}}/toolcache.json"
         },
+        {
+            "type": "file",
+            "source": "{{template_dir}}/toolset-2019.json",
+            "destination": "{{user `toolset_json_path`}}"
+        },
         {
             "type": "powershell",
             "environment_vars":[
@@ -301,6 +307,15 @@
                 "{{ template_dir }}/scripts/Installers/Download-ToolCache.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "environment_vars":[
+                "TOOLSET_JSON_PATH={{user `toolset_json_path`}}"
+            ],
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Install-Toolset.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
@@ -639,6 +654,15 @@
                 "{{ template_dir }}/scripts/Installers/Validate-ToolCache.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "environment_vars":[
+                "TOOLSET_JSON_PATH={{user `toolset_json_path`}}"
+            ],
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Validate-Toolset.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
@@ -886,6 +910,12 @@
                 "{{ template_dir }}/scripts/Installers/Validate-AliyunCli.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Validate-DiskSpace.ps1"
+            ]
+        },
         {
             "type": "file",
             "source": "C:\\InstalledSoftware.md",
diff --git a/images/win/Windows2019-Readme.md b/images/win/Windows2019-Readme.md
index c6d678e4..bee43de2 100644
--- a/images/win/Windows2019-Readme.md
+++ b/images/win/Windows2019-Readme.md
@@ -1,6 +1,6 @@
 # Windows Server 2019
 
-The following software is installed on machines with the 20200416.1 update.
+The following software is installed on machines with the 20200426.1 update.
 
 Components marked with **\*** have been upgraded since the previous version of the image.
 
@@ -25,7 +25,7 @@ _Environment:_
 
 ## Helm
 
-_Version:_ v3.1.2+gd878d4d<br/>
+_Version:_ v3.2.0+ge11b7ce<br/>
 _Environment:_
 * PATH: contains location of helm
 
@@ -145,8 +145,8 @@ _Environment:_
 
 ## Microsoft SSDT Visual Studio 2019 Extensions
 
-_Microsoft Analysis Services Projects Version:_ 2.9.7<br/>
-_SQL Server Integration Services Projects Version:_ 3.5<br/>
+_Microsoft Analysis Services Projects Version:_ 2.9.8<br/>
+_SQL Server Integration Services Projects Version:_ 3.6<br/>
 _Microsoft Reporting Services Projects Version:_ 2.6.5<br/>
 
 ## .NET 4.8
@@ -161,8 +161,8 @@ _WDK Visual Studio Extension Version:_ 10.0.18346.0<br/>
 
 ## Azure Service Fabric
 
-_SDK Version:_ 4.0.470.9590<br/>
-_Runtime Version:_ 7.0.470.9590
+_SDK Version:_ 4.1.409.9590<br/>
+_Runtime Version:_ 7.1.409.9590
 
 ## WinAppDriver
 
@@ -170,7 +170,7 @@ _Version:_ 1.1.1809.18001<br/>
 
 ## AWS CLI
 
-_Version:_ aws-cli 2.0.7<br/>
+_Version:_ aws-cli 2.0.9<br/>
 
 ## Android SDK Build Tools
 
@@ -421,10 +421,14 @@ _Description:_ .NET has been configured to use TLS 1.2 by default
 
 ## Azure CLI
 
-_Version:_ 2.3.1
+_Version:_ 2.4.0
 _Environment:_
 * PATH: contains location of az.cmd
 
+## AWS SAM CLI
+
+_Version:_ 0.47.0<br/>
+
 ## Azure DevOps Cli extension
 
 _Version:_ azure-devops                      0.18.0
@@ -439,7 +443,7 @@ _Version:_ 2.7.13 (x86)<br/>_Version:_ 3.6.9 (x86)<br/>
 
 ## Ruby
 
-_Version:_ 2.4.10 (x64)<br/>_Version:_ 2.5.8 (x64)<br/>_Version:_ 2.6.6 (x64)<br/>_Version:_ 2.7.1 (x64)<br/><br/>__System default version:__ Ruby 2.5.8p224<br/>_Environment:_<br/>* Location: C:\hostedtoolcache\windows\Ruby\2.5.8\x64\bin<br/>* PATH: contains the location of Ruby 2.5.8p224<br/>* Gem Version: 2.7.6.2<br/>
+_Version:_ 2.4.10 (x64)<br/>_Version:_ 2.5.8 (x64)<br/>_Version:_ 2.6.6 (x64)<br/>_Version:_ 2.7.1 (x64)<br/><br/>__System default version:__ Ruby 2.5.8p224<br/>_Environment:_<br/>* Location: C:\hostedtoolcache\windows\Ruby\2.5.8\x64\bin<br/>* PATH: contains the location of Ruby 2.5.8p224<br/>* Gem Version: 3.1.2<br/>
 
 ## OpenSSL
 
@@ -451,7 +455,7 @@ _Version:_ v5.30.2<br/>
 
 ## Git
 
-_Version:_ 2.26.1<br/>
+_Version:_ 2.26.2<br/>
 _Environment:_
 * PATH: contains location of git.exe
 
@@ -515,14 +519,14 @@ _Environment:_
 
 ## Rust (64-bit)
 
-#### 1.42.0
+#### 1.43.0
 _Location:_ C:\Rust\.cargo\bin
 _Environment:_
 * PATH: contains the location of rustc.exe
 
 ## Julia (x64)
 
-_Version:_ 1.4.0<br/>
+_Version:_ 1.4.1<br/>
 
 ## Subversion
 
@@ -537,12 +541,12 @@ _Environment:_
 ## Google Chrome
 
 _version:_
-81.0.4044.113
+81.0.4044.122
 
 ## Microsoft Edge
 
 _version:_
-81.0.416.53
+81.0.416.64
 
 ## Mozilla Firefox
 
@@ -579,7 +583,7 @@ _Environment:_
 #### Microsoft Edge Driver
 
 _version:_
-81.0.416.53
+81.0.416.64
 
 _Environment:_
 * EdgeWebDriver: location of msedgedriver.exe
@@ -659,7 +663,9 @@ _Environment:_
 
 _SDK:_
 * 3.1.201 C:\Program Files\dotnet\sdk\3.1.201
+* 3.1.200 C:\Program Files\dotnet\sdk\3.1.200
 * 3.1.103 C:\Program Files\dotnet\sdk\3.1.103
+* 3.1.102 C:\Program Files\dotnet\sdk\3.1.102
 * 3.1.101 C:\Program Files\dotnet\sdk\3.1.101
 * 3.1.100 C:\Program Files\dotnet\sdk\3.1.100
 * 2.2.402 C:\Program Files\dotnet\sdk\2.2.402
@@ -721,6 +727,7 @@ _SDK:_
 
 _Runtime:_
 * 3.1.3 C:\Program Files\dotnet\shared\Microsoft.NETCore.App\3.1.3
+* 3.1.2 C:\Program Files\dotnet\shared\Microsoft.NETCore.App\3.1.2
 * 3.1.1 C:\Program Files\dotnet\shared\Microsoft.NETCore.App\3.1.1
 * 3.1.0 C:\Program Files\dotnet\shared\Microsoft.NETCore.App\3.1.0
 * 2.2.8 C:\Program Files\dotnet\shared\Microsoft.NETCore.App\2.2.8
@@ -836,7 +843,7 @@ _Version_: 2.8.4+ff0de50053 - shim 0.8.1<br/>
 
 ## Kubectl
 
-_Version:_ Client Version: v1.18.1<br/>
+_Version:_ Client Version: v1.18.2<br/>
 _Environment:_
 * PATH: contains location of kubectl.exe
 
@@ -848,11 +855,11 @@ _Environment:_
 
 ## bazel
 
-_Version:_ bazel 3.0.0<br/>
+_Version:_ bazel 3.1.0<br/>
 
 ## bazelisk
 
-_Version:_ 1.3.0<br/>
+_Version:_ 1.4.0<br/>
 
 ## Alibaba Cloud CLI
 
diff --git a/images/win/scripts/ImageHelpers/ImageHelpers.psm1 b/images/win/scripts/ImageHelpers/ImageHelpers.psm1
index f979659d..2b716880 100644
--- a/images/win/scripts/ImageHelpers/ImageHelpers.psm1
+++ b/images/win/scripts/ImageHelpers/ImageHelpers.psm1
@@ -15,6 +15,7 @@ Export-ModuleMember -Function @(
     'Set-SystemVariable'
     'Install-Binary'
     'Get-ToolcachePackages'
+    'Get-ToolsetContent'
     'Get-ToolsByName'
     'Add-ContentToMarkdown'
     'Add-SoftwareDetailsToMarkdown'
diff --git a/images/win/scripts/ImageHelpers/InstallHelpers.ps1 b/images/win/scripts/ImageHelpers/InstallHelpers.ps1
index ee528780..c8d70c8b 100644
--- a/images/win/scripts/ImageHelpers/InstallHelpers.ps1
+++ b/images/win/scripts/ImageHelpers/InstallHelpers.ps1
@@ -283,6 +283,11 @@ function Get-ToolcachePackages {
     Get-Content -Raw $toolcachePath | ConvertFrom-Json
 }
 
+function Get-ToolsetContent {
+    $toolsetJson = Get-Content -Path $env:TOOLSET_JSON_PATH -Raw
+    ConvertFrom-Json -InputObject $toolsetJson
+}
+
 function Get-ToolsByName {
     param (
         [Parameter(Mandatory = $True)]
diff --git a/images/win/scripts/Installers/Download-ToolCache.ps1 b/images/win/scripts/Installers/Download-ToolCache.ps1
index 4749a3f3..6c93e380 100644
--- a/images/win/scripts/Installers/Download-ToolCache.ps1
+++ b/images/win/scripts/Installers/Download-ToolCache.ps1
@@ -44,21 +44,6 @@ Function NPMFeed-AuthSetup {
     $npmrcContent | Out-File -FilePath "$($env:TEMP)/.npmrc" -Encoding utf8
 }
 
-Function Set-DefaultPythonVersion {
-    param(
-        [Parameter(Mandatory=$true)]
-        [System.Version] $Version,
-        [System.String] $Arch = "x64"
-    )
-
-    $pythonPath = $Env:AGENT_TOOLSDIRECTORY + "/Python/${Version}*/${Arch}"
-    $pythonDir = Get-Item -Path $pythonPath
-
-    Write-Host "Use Python ${Version} as a system Python"
-    Add-MachinePathItem -PathItem $pythonDir.FullName
-    Add-MachinePathItem -PathItem "$($pythonDir.FullName)\Scripts"
-}
-
 Function Set-DefaultRubyVersion {
     param(
         [Parameter(Mandatory=$true)]
@@ -106,5 +91,4 @@ $ToolVersions.PSObject.Properties | ForEach-Object {
     }
 }
 
-Set-DefaultPythonVersion -Version "3.7"
 Set-DefaultRubyVersion -Version "2.5"
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Install-JavaTools.ps1 b/images/win/scripts/Installers/Install-JavaTools.ps1
index e88fc745..96282371 100644
--- a/images/win/scripts/Installers/Install-JavaTools.ps1
+++ b/images/win/scripts/Installers/Install-JavaTools.ps1
@@ -8,22 +8,26 @@
 $azulJDK7Uri = 'https://repos.azul.com/azure-only/zulu/packages/zulu-7/7u232/zulu-7-azure-jdk_7.31.0.5-7.0.232-win_x64.zip'
 $azulJDK8Uri = 'https://repos.azul.com/azure-only/zulu/packages/zulu-8/8u222/zulu-8-azure-jdk_8.40.0.25-8.0.222-win_x64.zip'
 $azulJDK11Uri = 'https://repos.azul.com/azure-only/zulu/packages/zulu-11/11.0.4/zulu-11-azure-jdk_11.33.15-11.0.4-win_x64.zip'
+$azulJDK13Uri = 'https://repos.azul.com/azure-only/zulu/packages/zulu-13/13.0.3/zulu-13-azure-jdk_13.31.11-13.0.3-win_x64.zip'
 
 cd $env:TEMP
 
 Invoke-WebRequest -UseBasicParsing -Uri $azulJDK7Uri -OutFile azulJDK7.zip
 Invoke-WebRequest -UseBasicParsing -Uri $azulJDK8Uri -OutFile azulJDK8.zip
 Invoke-WebRequest -UseBasicParsing -Uri $azulJDK11Uri -OutFile azulJDK11.zip
+Invoke-WebRequest -UseBasicParsing -Uri $azulJDK13Uri -OutFile azulJDK13.zip
 
 # Expand the zips
 Expand-Archive -Path azulJDK7.zip -DestinationPath "C:\Program Files\Java\" -Force
 Expand-Archive -Path azulJDK8.zip -DestinationPath "C:\Program Files\Java\" -Force
 Expand-Archive -Path azulJDK11.zip -DestinationPath "C:\Program Files\Java\" -Force
+Expand-Archive -Path azulJDK13.zip -DestinationPath "C:\Program Files\Java\" -Force
 
 # Deleting zip folders
 Remove-Item -Recurse -Force azulJDK7.zip
 Remove-Item -Recurse -Force azulJDK8.zip
 Remove-Item -Recurse -Force azulJDK11.zip
+Remove-Item -Recurse -Force azulJDK13.zip
 
 Import-Module -Name ImageHelpers -Force
 
@@ -49,6 +53,9 @@ $latestJava8Install = $java8Installs.FullName;
 $java11Installs = Get-ChildItem -Path 'C:\Program Files\Java' -Filter '*azure-jdk*11*' | Sort-Object -Property Name -Descending | Select-Object -First 1
 $latestJava11Install = $java11Installs.FullName;
 
+$java13Installs = Get-ChildItem -Path 'C:\Program Files\Java' -Filter '*azure-jdk*13*' | Sort-Object -Property Name -Descending | Select-Object -First 1
+$latestJava13Install = $java13Installs.FullName;
+
 $newPath = [string]::Join(';', $newPathSegments)
 $newPath = $latestJava8Install + '\bin;' + $newPath
 
@@ -58,6 +65,7 @@ setx JAVA_HOME $latestJava8Install /M
 setx JAVA_HOME_7_X64 $latestJava7Install /M
 setx JAVA_HOME_8_X64 $latestJava8Install /M
 setx JAVA_HOME_11_X64 $latestJava11Install /M
+setx JAVA_HOME_13_X64 $latestJava13Install /M
 
 # Install Java tools
 # Force chocolatey to ignore dependencies on Ant and Maven or else they will download the Oracle JDK
diff --git a/images/win/scripts/Installers/Install-Toolset.ps1 b/images/win/scripts/Installers/Install-Toolset.ps1
new file mode 100644
index 00000000..25bfe58e
--- /dev/null
+++ b/images/win/scripts/Installers/Install-Toolset.ps1
@@ -0,0 +1,76 @@
+################################################################################
+##  File:  Install-Toolset.ps1
+##  Team:  CI-Build
+##  Desc:  Install toolset
+################################################################################
+
+Function Install-Asset {
+    param(
+        [Parameter(Mandatory=$true)]
+        [object] $ReleaseAsset
+    )
+
+    $releaseAssetName = [System.IO.Path]::GetFileNameWithoutExtension($ReleaseAsset.filename)
+    $assetFolderPath = Join-Path $env:TEMP $releaseAssetName
+    $assetArchivePath = Start-DownloadWithRetry -Url $ReleaseAsset.download_url -Name $ReleaseAsset.filename
+
+    Write-Host "Extract $($ReleaseAsset.filename) content..."
+    7z.exe x $assetArchivePath -o"$assetFolderPath" -y | Out-Null
+
+    Write-Host "Invoke installation script..."
+    Push-Location -Path $assetFolderPath
+    Invoke-Expression .\setup.ps1
+    Pop-Location
+}
+
+Function Set-DefaultPythonVersion {
+    param(
+        [Parameter(Mandatory=$true)]
+        [object[]] $Toolset
+    )
+
+    $python = $Toolset  | Where-Object { ($_.name -eq "Python") -and ($_.default -ne "") } `
+                        | Select-Object default, arch -First 1
+
+    if ($python.default -ne $null) {
+        $pythonPath = Join-Path $Env:AGENT_TOOLSDIRECTORY "/Python/$($python.default)/$($python.arch)" -Resolve
+
+        Write-Host "Use Python $($python.default) as a system Python"
+        Add-MachinePathItem -PathItem $pythonPath
+        Add-MachinePathItem -PathItem "$pythonPath\Scripts"
+    } else {
+        Write-Host "Default Python version not found in toolset file!"
+    }
+}
+
+$ErrorActionPreference = "Stop"
+
+Import-Module -Name ImageHelpers -Force
+
+# Get toolcache content from toolset
+$tools = Get-ToolsetContent | Select-Object -ExpandProperty toolcache
+
+foreach ($tool in $tools) {
+    # Get versions manifest for current tool
+    $assets = Invoke-RestMethod $tool.url
+
+    # Get github release asset for each version
+    foreach ($toolVersion in $tool.versions) {
+        $asset = $assets | Where-Object version -like $toolVersion `
+                         | Sort-Object -Property {[version]$_.version} -Descending `
+                         | Select-Object -ExpandProperty files `
+                         | Where-Object { ($_.platform -eq $tool.platform) -and ($_.arch -eq $tool.arch) } `
+                         | Select-Object -First 1
+
+        Write-Host "Installing $($tool.name) $toolVersion $($tool.arch)..."
+        if ($asset -ne $null) {
+            Install-Asset -ReleaseAsset $asset
+        } else {
+            Write-Host "Asset was not found in versions manifest"
+            exit 1
+        }
+    }
+}
+
+# Install default python version
+Set-DefaultPythonVersion -Toolset $tools
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Validate-DiskSpace.ps1 b/images/win/scripts/Installers/Validate-DiskSpace.ps1
new file mode 100644
index 00000000..d5b4f996
--- /dev/null
+++ b/images/win/scripts/Installers/Validate-DiskSpace.ps1
@@ -0,0 +1,14 @@
+################################################################################
+##  File:  Validate-DiskSpace.ps1
+##  Desc:  Validate free disk space
+################################################################################
+
+$availableSpaceMB =  [math]::Round((Get-PSDrive -Name C).Free / 1MB)
+$minimumFreeSpaceMB = 15 * 1024
+
+Write-Host "Available disk space: $availableSpaceMB MB"
+if ($availableSpaceMB -le $minimumFreeSpaceMB)
+{
+    Write-Host "Not enough disk space on the image (minimum available space: $minimumFreeSpaceMB MB)"
+    exit 1
+}
diff --git a/images/win/scripts/Installers/Validate-JavaTools.ps1 b/images/win/scripts/Installers/Validate-JavaTools.ps1
index 71477689..33f90694 100644
--- a/images/win/scripts/Installers/Validate-JavaTools.ps1
+++ b/images/win/scripts/Installers/Validate-JavaTools.ps1
@@ -36,6 +36,12 @@ if( $( $(& $env:comspec "/s /c java -version 2>&1") | Out-String) -match  '^(?<v
    $java11Version = $Matches.version
 }
 
+$env:Path = $env:JAVA_HOME_13_X64 + "\bin;" + $env:Path
+
+if( $( $(& $env:comspec "/s /c java -version 2>&1") | Out-String) -match  '^(?<vendor>.+) version "(?<version>.+)".*' )
+{
+   $java13Version = $Matches.version
+}
 
 if( $(ant -version) -match  'Apache Ant\(TM\) version (?<version>.*) compiled.*' )
 {
@@ -69,6 +75,10 @@ _Location:_ $env:JAVA_HOME_7_X64
 #### $java11Version
 
 _Location:_ $env:JAVA_HOME_11_X64
+
+#### $java13Version
+
+_Location:_ $env:JAVA_HOME_13_X64
 "@
 
 Add-SoftwareDetailsToMarkdown -SoftwareName $SoftwareName -DescriptionMarkdown $Description
diff --git a/images/win/scripts/Installers/Validate-ToolCache.ps1 b/images/win/scripts/Installers/Validate-ToolCache.ps1
index 5ad500bf..526254e2 100644
--- a/images/win/scripts/Installers/Validate-ToolCache.ps1
+++ b/images/win/scripts/Installers/Validate-ToolCache.ps1
@@ -63,32 +63,6 @@ function RunTestsByPath {
     }
 }
 
-function Get-SystemDefaultPython {
-    Write-Host "Validate system Python..."
-
-    if (Get-Command -Name 'python')
-    {
-        Write-Host "Python $(& python -V 2>&1) on path"
-    }
-    else
-    {
-        Write-Host "Python is not on path"
-        exit 1
-    }
-
-    $pythonBinVersion = $(& python -V 2>&1)
-    if ($pythonBinVersion -notlike "Python 3.*")
-    {
-        Write-Error "Python 3 is not in the PATH"
-        exit 1
-    }
-
-    $pythonBinOnPath = Split-Path -Path (Get-Command -Name 'python').Path
-    $description = GetDefaultToolDescription -SoftwareVersion $pythonBinVersion -SoftwareLocation $pythonBinOnPath
-
-    return $description
-}
-
 function Get-SystemDefaultRuby {
     Write-Host "Validate system Ruby..."
 
@@ -196,9 +170,6 @@ function ToolcacheTest {
         }
     }
 
-    if ($SoftwareName -contains "Python") {
-        $markdownDescription += Get-SystemDefaultPython
-    }
     if ($SoftwareName -contains "Ruby") {
         $markdownDescription += Get-SystemDefaultRuby
     }
@@ -206,10 +177,6 @@ function ToolcacheTest {
     Add-SoftwareDetailsToMarkdown -SoftwareName $SoftwareName -DescriptionMarkdown $markdownDescription
 }
 
-# Python test
-$PythonTests = @("python.exe", "Scripts\pip.exe")
-ToolcacheTest -SoftwareName "Python" -ExecTests $PythonTests
-
 # PyPy test
 $PyPyTests = @("python.exe", "bin\pip.exe")
 ToolcacheTest -SoftwareName "PyPy" -ExecTests $PyPyTests
diff --git a/images/win/scripts/Installers/Validate-Toolset.ps1 b/images/win/scripts/Installers/Validate-Toolset.ps1
new file mode 100644
index 00000000..28963b12
--- /dev/null
+++ b/images/win/scripts/Installers/Validate-Toolset.ps1
@@ -0,0 +1,111 @@
+################################################################################
+##  File:  Validate-Toolset.ps1
+##  Team:  CI-Build
+##  Desc:  Validate Toolset
+################################################################################
+
+function Run-ExecutableTests {
+    param (
+        [Parameter(Mandatory)] [string[]] $Executables,
+        [Parameter(Mandatory)] [string] $ToolPath
+    )
+
+    foreach ($executable in $Executables) {
+        $executablePath = Join-Path $ToolPath $executable
+
+        Write-Host "Check $executable..."
+        if (Test-Path $executablePath) {
+            Write-Host "$executable is successfully installed: $(& $executablePath --version)"
+        } else {
+            Write-Host "$executablePath is not installed!"
+            exit 1
+        }
+    }
+}
+
+function Validate-SystemDefaultTool {
+    param (
+        [Parameter(Mandatory)] [string] $ToolName,
+        [Parameter(Mandatory)] [string] $ExpectedVersion
+    )
+
+    $binName = $ToolName.ToLower()
+
+    # Check if tool on path
+    if (Get-Command -Name $binName) {
+        $versionOnPath = $(& $binName --version 2>&1) | Select-String -Pattern ".*(\d+\.\d+\.\d+)"
+        $versionBinPath = Split-Path -Path (Get-Command -Name $binName).Path
+
+        # Check if version is correct
+        if ($versionOnPath.matches.Groups[1].Value -notlike $ExpectedVersion) {
+            Write-Error "$ToolName $ExpectedVersion is not in the PATH"
+            exit 1
+        }
+
+        Write-Host "$ToolName $versionOnPath on path"
+    } else {
+        Write-Host "$ToolName is not on path"
+        exit 1
+    }
+
+    # Add default version description to markdown
+    $description = "<br/>__System default version:__ $versionOnPath<br/>"
+    $description += "_Environment:_<br/>"
+    $description += "* Location: $versionBinPath<br/>"
+    $description += "* PATH: contains the location of $versionOnPath<br/>"
+
+    return $description
+}
+
+$ErrorActionPreference = "Stop"
+
+Import-Module -Name ImageHelpers -Force
+
+# Define executables for cached tools
+$toolsExecutables = @{ Python = @("python.exe", "Scripts\pip.exe") }
+
+# Get toolcache content from toolset
+$tools = Get-ToolsetContent | Select-Object -ExpandProperty toolcache
+
+foreach($tool in $tools) {
+    $markdownDescription = ""
+
+    $toolPath = Join-Path $env:AGENT_TOOLSDIRECTORY $tool.name
+    # Get executables for current tool
+    $toolExecs = $toolsExecutables[$tool.name]
+
+    foreach ($version in $tool.versions) {
+        # Check if version folder exists
+        $expectedVersionPath = Join-Path $toolPath $version
+        if (-not (Test-Path $expectedVersionPath)) {
+            Write-Host "Expected $($tool.name) $version folder is not found!"
+            exit 1
+        }
+
+        # Take latest installed version in case if toolset version contains wildcards
+        $foundVersion = Get-Item $expectedVersionPath `
+                        | Sort-Object -Property {[version]$_.name} -Descending `
+                        | Select-Object -First 1
+
+        # Check for required architecture folder
+        $foundVersionArchPath = Join-Path $foundVersion $tool.arch
+        if (-not (Test-Path $foundVersionArchPath)) {
+            Write-Host "Expected $($tool.name)($($tool.arch)) $($foundVersion.name) architecture folder is not found!"
+            exit 1
+        }
+
+        Write-Host "Run validation test for $($tool.name)($($tool.arch)) $($foundVersion.name) executables..."
+        Run-ExecutableTests -Executables $toolExecs -ToolPath $foundVersionArchPath
+
+        # Add to tool version to markdown
+        $markdownDescription += "_Version:_ $($foundVersion.name)<br/>"
+    }
+
+    # Create markdown description for system default tool
+    if (-not ([string]::IsNullOrEmpty($tool.default))) {
+        Write-Host "Validate system default $($tool.name)($($tool.arch)) $($tool.default)..."
+        $markdownDescription += Validate-SystemDefaultTool -ToolName $tool.name -ExpectedVersion $tool.default
+    }
+
+    Add-SoftwareDetailsToMarkdown -SoftwareName "$($tool.name) ($($tool.arch))" -DescriptionMarkdown $markdownDescription
+}
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1 b/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1
index d8fa7a05..202c9b48 100644
--- a/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1
+++ b/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1
@@ -61,6 +61,15 @@ Install-WindowsFeature -Name NET-Framework-45-Features -IncludeAllSubFeature
 Install-WindowsFeature -Name BITS -IncludeAllSubFeature
 Install-WindowsFeature -Name DSC-Service
 
+# Install FS-iSCSITarget-Server
+$fsResult = Install-WindowsFeature -Name FS-iSCSITarget-Server -IncludeAllSubFeature -IncludeManagementTools
+if ( $fsResult.Success ) {
+    Write-Host "FS-iSCSITarget-Server has been successfully installed"
+} else {
+    Write-Host "Failed to install FS-iSCSITarget-Server"
+    exit 1
+}
+
 Write-Host "Disable UAC"
 Disable-UserAccessControl
 
@@ -135,6 +144,7 @@ wmic logicaldisk get size,freespace,caption
 # Adding description of the software to Markdown
 
 $Content = @"
+<!--- DO NOT EDIT - This markdown file is autogenerated. -->
 # Windows Server 2016
 
 The following software is installed on machines with the $env:ImageVersion update.
diff --git a/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1 b/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1
index 92e153d7..12feeabe 100644
--- a/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1
+++ b/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1
@@ -57,6 +57,14 @@ Install-WindowsFeature -Name NET-Framework-Features -IncludeAllSubFeature
 # Explicitly install all 4.7 sub features to include ASP.Net.
 # As of  1/16/2019, WinServer 19 lists .Net 4.7 as NET-Framework-45-Features
 Install-WindowsFeature -Name NET-Framework-45-Features -IncludeAllSubFeature
+# Install FS-iSCSITarget-Server
+$fsResult = Install-WindowsFeature -Name FS-iSCSITarget-Server -IncludeAllSubFeature -IncludeManagementTools
+if ( $fsResult.Success ) {
+    Write-Host "FS-iSCSITarget-Server has been successfully installed"
+} else {
+    Write-Host "Failed to install FS-iSCSITarget-Server"
+    exit 1
+}
 
 Write-Host "Disable UAC"
 Disable-UserAccessControl
@@ -129,6 +137,7 @@ wmic logicaldisk get size,freespace,caption
 # Adding description of the software to Markdown
 
 $Content = @"
+<!--- DO NOT EDIT - This markdown file is autogenerated. -->
 # Windows Server 2019
 
 The following software is installed on machines with the $env:ImageVersion update.
diff --git a/images/win/toolcache-2016.json b/images/win/toolcache-2016.json
index 8db575c2..1b4f1a6c 100644
--- a/images/win/toolcache-2016.json
+++ b/images/win/toolcache-2016.json
@@ -1,10 +1,4 @@
 {
-    "@actions/toolcache-python-windows-x64": [
-        "2.7", "3.5", "3.6", "3.7", "3.8"
-    ],
-    "@actions/toolcache-python-windows-x86": [
-        "2.7", "3.5", "3.6", "3.7", "3.8"
-    ],
     "@actions/toolcache-ruby-windows-x64": [
         "2.4", "2.5", "2.6", "2.7"
     ],
diff --git a/images/win/toolcache-2019.json b/images/win/toolcache-2019.json
index 4f946cfa..6873c14e 100644
--- a/images/win/toolcache-2019.json
+++ b/images/win/toolcache-2019.json
@@ -1,10 +1,4 @@
 {
-    "@actions/toolcache-python-windows-x64": [
-        "2.7", "3.5", "3.6", "3.7", "3.8"
-    ],
-    "@actions/toolcache-python-windows-x86": [
-        "2.7", "3.5", "3.6", "3.7", "3.8"
-    ],
     "@actions/toolcache-ruby-windows-x64": [
         "2.4", "2.5", "2.6", "2.7"
     ],
diff --git a/images/win/toolset-2016.json b/images/win/toolset-2016.json
new file mode 100644
index 00000000..da372c49
--- /dev/null
+++ b/images/win/toolset-2016.json
@@ -0,0 +1,31 @@
+{
+    "toolcache": [
+        {
+            "name": "Python",
+            "url" : "https://raw.githubusercontent.com/actions/python-versions/master/versions-manifest.json",
+            "arch": "x64",
+            "platform" : "win32",
+            "versions": [
+                "2.7.*",
+                "3.5.*",
+                "3.6.*",
+                "3.7.*",
+                "3.8.*"
+            ],
+            "default": "3.7.*"
+        },
+        {
+            "name": "Python",
+            "url" : "https://raw.githubusercontent.com/actions/python-versions/master/versions-manifest.json",
+            "arch": "x86",
+            "platform" : "win32",
+            "versions": [
+                "2.7.*",
+                "3.5.*",
+                "3.6.*",
+                "3.7.*",
+                "3.8.*"
+            ]
+        }
+    ]
+}
\ No newline at end of file
diff --git a/images/win/toolset-2019.json b/images/win/toolset-2019.json
new file mode 100644
index 00000000..da372c49
--- /dev/null
+++ b/images/win/toolset-2019.json
@@ -0,0 +1,31 @@
+{
+    "toolcache": [
+        {
+            "name": "Python",
+            "url" : "https://raw.githubusercontent.com/actions/python-versions/master/versions-manifest.json",
+            "arch": "x64",
+            "platform" : "win32",
+            "versions": [
+                "2.7.*",
+                "3.5.*",
+                "3.6.*",
+                "3.7.*",
+                "3.8.*"
+            ],
+            "default": "3.7.*"
+        },
+        {
+            "name": "Python",
+            "url" : "https://raw.githubusercontent.com/actions/python-versions/master/versions-manifest.json",
+            "arch": "x86",
+            "platform" : "win32",
+            "versions": [
+                "2.7.*",
+                "3.5.*",
+                "3.6.*",
+                "3.7.*",
+                "3.8.*"
+            ]
+        }
+    ]
+}
\ No newline at end of file