diff --git a/images/linux/scripts/helpers/install.sh b/images/linux/scripts/helpers/install.sh
index 0f90ac4a..232a7353 100644
--- a/images/linux/scripts/helpers/install.sh
+++ b/images/linux/scripts/helpers/install.sh
@@ -14,9 +14,9 @@ download_with_retries() {
     local COMPRESSED="$4"
 
     if [ $COMPRESSED == "compressed" ]; then
-        COMMAND="curl $URL -4 -s --compressed -o '$DEST/$NAME'"
+        COMMAND="curl $URL -4 -sL --compressed -o '$DEST/$NAME'"
     else
-        COMMAND="curl $URL -4 -s -o '$DEST/$NAME'"
+        COMMAND="curl $URL -4 -sL -o '$DEST/$NAME'"
     fi
 
     echo "Downloading $URL..."
diff --git a/images/linux/scripts/installers/1604/basic.sh b/images/linux/scripts/installers/1604/basic.sh
deleted file mode 100644
index 2abfda60..00000000
--- a/images/linux/scripts/installers/1604/basic.sh
+++ /dev/null
@@ -1,84 +0,0 @@
-#!/bin/bash
-################################################################################
-##  File:  basic.sh
-##  Desc:  Installs basic command line utilities and dev packages
-################################################################################
-
-# Source the helpers for use with the script
-source $HELPER_SCRIPTS/document.sh
-
-set -e
-
-common_packages="dnsutils
-                 iproute2
-                 iputils-ping
-                 libc++-dev
-                 libc++abi-dev
-                 libcurl3
-                 libicu55
-                 libunwind8
-                 locales
-                 openssh-client
-                 tzdata
-                 zstd
-                 lib32z1
-                 libxkbfile-dev
-                 pkg-config
-                 libsecret-1-dev
-                 libxss1
-                 libgconf-2-4
-                 dbus
-                 xvfb
-                 libgbm-dev
-                 libgtk-3-0
-                 tk
-                 fakeroot
-                 dpkg
-                 rpm
-                 xz-utils
-                 xorriso
-                 zsync
-                 gnupg2
-                 texinfo"
-
-cmd_packages="curl
-              file
-              ftp
-              jq
-              netcat
-              ssh
-              parallel
-              rsync
-              shellcheck
-              sudo
-              telnet
-              time
-              unzip
-              zip
-              wget
-              upx
-              m4
-              bison
-              flex"
-
-# Install basic command-line utilities
-for package in $common_packages $cmd_packages; do
-    echo "Install $package"
-    apt-fast install -y --no-install-recommends $package
-done
-
-# Run tests to determine that the software installed as expected
-echo "Testing to make sure that script performed as expected, and basic scenarios work"
-for cmd in $cmd_packages; do
-    if ! command -v $cmd; then
-        echo "$cmd was not installed"
-        exit 1
-    fi
-done
-
-# Document what was added to the image
-echo "Lastly, documenting what we added to the metadata file"
-DocumentInstalledItem "Basic packages:"
-for package in $common_packages $cmd_packages; do
-    DocumentInstalledItemIndent $package
-done
diff --git a/images/linux/scripts/installers/basic.sh b/images/linux/scripts/installers/basic.sh
index 3caf0d06..b6bd5377 100644
--- a/images/linux/scripts/installers/basic.sh
+++ b/images/linux/scripts/installers/basic.sh
@@ -37,7 +37,8 @@ common_packages="dnsutils
                  zsync
                  gnupg2
                  lib32z1
-                 texinfo"
+                 texinfo
+                 libsqlite3-dev"
 
 cmd_packages="curl
               file
@@ -56,7 +57,10 @@ cmd_packages="curl
               wget
               m4
               bison
-              flex"
+              flex
+              patchelf
+              bzip2
+              sqlite3"
 
 if isUbuntu20 ; then
     echo "Install python2"
@@ -64,7 +68,7 @@ if isUbuntu20 ; then
 fi
 
 echo "Install libcurl"
-if isUbuntu18 ; then
+if isUbuntu16 || isUbuntu18; then
    libcurelVer="libcurl3"
 fi
 
@@ -74,12 +78,19 @@ fi
 
 apt-get install -y --no-install-recommends $libcurelVer
 
+# install additional packages only for Ubuntu16.04
+if isUbuntu16; then
+    common_packages="$common_packages
+            libc++-dev
+            libc++abi-dev
+            libicu55"
+fi
+
 for package in $common_packages $cmd_packages; do
     echo "Install $package"
     apt-get install -y --no-install-recommends $package
 done
 
-
 # Run tests to determine that the software installed as expected
 echo "Testing to make sure that script performed as expected, and basic scenarios work"
 for cmd in $cmd_packages; do
diff --git a/images/linux/scripts/installers/oras-cli.sh b/images/linux/scripts/installers/oras-cli.sh
new file mode 100644
index 00000000..c4546ccb
--- /dev/null
+++ b/images/linux/scripts/installers/oras-cli.sh
@@ -0,0 +1,30 @@
+#!/bin/bash
+################################################################################
+##  File:  oras-cli.sh
+##  Desc:  Installs ORAS CLI
+################################################################################
+
+# Source the helpers for use with the script
+source $HELPER_SCRIPTS/document.sh
+source $HELPER_SCRIPTS/install.sh
+
+# Determine latest ORAS CLI version
+ORAS_CLI_LATEST_VERSION_URL=https://api.github.com/repos/deislabs/oras/releases/latest
+ORAS_CLI_DOWNLOAD_URL=$(curl -s $ORAS_CLI_LATEST_VERSION_URL | jq -r '.assets[].browser_download_url | select(contains("linux_amd64.tar.gz"))')
+ORAS_CLI_ARCHIVE=$(basename $ORAS_CLI_DOWNLOAD_URL)
+
+# Install ORAS CLI
+cd /tmp
+download_with_retries $ORAS_CLI_DOWNLOAD_URL
+tar -zxvf $ORAS_CLI_ARCHIVE -C /usr/local/bin oras
+
+# Run tests to determine that the software installed as expected
+echo "Testing to make sure that script performed as expected, and basic scenarios work"
+if ! oras version; then
+    echo "ORAS CLI was not installed"
+    exit 1
+fi
+
+# Document what was added to the image
+echo "Lastly, documenting what we added to the metadata file"
+DocumentInstalledItem "ORAS CLI $(oras version | awk 'NR==1{print $2}')"
\ No newline at end of file
diff --git a/images/linux/scripts/installers/rust.sh b/images/linux/scripts/installers/rust.sh
index 605bce11..824ec899 100644
--- a/images/linux/scripts/installers/rust.sh
+++ b/images/linux/scripts/installers/rust.sh
@@ -19,13 +19,15 @@ source $CARGO_HOME/env
 # Install common tools
 rustup component add rustfmt clippy
 cargo install bindgen cbindgen
+cargo install cargo-audit
+cargo install cargo-outdated
 
 echo "Test installation of the Rust toochain"
 
 # Permissions
 chmod -R 777 $(dirname $RUSTUP_HOME)
 
-for cmd in rustup rustc rustdoc cargo rustfmt cargo-clippy bindgen cbindgen; do
+for cmd in rustup rustc rustdoc cargo rustfmt cargo-clippy bindgen cbindgen 'cargo audit' 'cargo outdated'; do
     if ! command -v $cmd --version; then
         echo "$cmd was not installed or is not found on the path"
         exit 1
@@ -54,3 +56,5 @@ DocumentInstalledItem "clippy ($(cargo-clippy --version 2>&1 | cut -d ' ' -f 2))
 DocumentInstalledItem "rustdoc ($(rustdoc --version 2>&1 | cut -d ' ' -f 2))"
 DocumentInstalledItem "bindgen ($(bindgen --version 2>&1 | cut -d ' ' -f 2))"
 DocumentInstalledItem "cbindgen ($(cbindgen --version 2>&1 | cut -d ' ' -f 2))"
+DocumentInstalledItem "cargo audit ($(cargo audit --version 2>&1 | cut -d ' ' -f 2))"
+DocumentInstalledItem "cargo outdated ($(cargo outdated --version 2>&1 | cut -d ' ' -f 2))"
\ No newline at end of file
diff --git a/images/linux/ubuntu1604.json b/images/linux/ubuntu1604.json
index 8567d2cc..23a4bf88 100644
--- a/images/linux/ubuntu1604.json
+++ b/images/linux/ubuntu1604.json
@@ -143,7 +143,7 @@
                 "{{template_dir}}/scripts/installers/azcopy.sh",
                 "{{template_dir}}/scripts/installers/azure-cli.sh",
                 "{{template_dir}}/scripts/installers/azure-devops-cli.sh",
-                "{{template_dir}}/scripts/installers/1604/basic.sh",
+                "{{template_dir}}/scripts/installers/basic.sh",
                 "{{template_dir}}/scripts/installers/aliyun-cli.sh",
                 "{{template_dir}}/scripts/installers/aws.sh",
                 "{{template_dir}}/scripts/installers/build-essential.sh",
@@ -177,6 +177,7 @@
                 "{{template_dir}}/scripts/installers/mysql.sh",
                 "{{template_dir}}/scripts/installers/nodejs.sh",
                 "{{template_dir}}/scripts/installers/bazel.sh",
+                "{{template_dir}}/scripts/installers/oras-cli.sh",
                 "{{template_dir}}/scripts/installers/phantomjs.sh",
                 "{{template_dir}}/scripts/installers/php.sh",
                 "{{template_dir}}/scripts/installers/pollinate.sh",
diff --git a/images/linux/ubuntu1804.json b/images/linux/ubuntu1804.json
index 56be34c1..cad08ebb 100644
--- a/images/linux/ubuntu1804.json
+++ b/images/linux/ubuntu1804.json
@@ -181,6 +181,7 @@
                 "{{template_dir}}/scripts/installers/nvm.sh",
                 "{{template_dir}}/scripts/installers/nodejs.sh",
                 "{{template_dir}}/scripts/installers/bazel.sh",
+                "{{template_dir}}/scripts/installers/oras-cli.sh",
                 "{{template_dir}}/scripts/installers/phantomjs.sh",
                 "{{template_dir}}/scripts/installers/php.sh",
                 "{{template_dir}}/scripts/installers/pollinate.sh",
diff --git a/images/linux/ubuntu2004.json b/images/linux/ubuntu2004.json
index a43a79ed..95f0a481 100644
--- a/images/linux/ubuntu2004.json
+++ b/images/linux/ubuntu2004.json
@@ -183,6 +183,7 @@
                 "{{template_dir}}/scripts/installers/nvm.sh",
                 "{{template_dir}}/scripts/installers/nodejs.sh",
                 "{{template_dir}}/scripts/installers/bazel.sh",
+                "{{template_dir}}/scripts/installers/oras-cli.sh",
                 "{{template_dir}}/scripts/installers/phantomjs.sh",
                 "{{template_dir}}/scripts/installers/php.sh",
                 "{{template_dir}}/scripts/installers/pollinate.sh",
diff --git a/images/macos/macos-10.15-Readme.md b/images/macos/macos-10.15-Readme.md
index 6936556d..4fbba9f5 100644
--- a/images/macos/macos-10.15-Readme.md
+++ b/images/macos/macos-10.15-Readme.md
@@ -2,7 +2,7 @@
 - System Version: macOS 10.15.5 (19F101)
 - Kernel Version: Darwin 19.5.0
 - System Integrity Protection: Enabled
-- Image Version: 20200625.2
+- Image Version: 20200702.1
 
 ## Installed Software
 ### Language and Runtime
@@ -18,9 +18,9 @@
 - gcc-9 (Homebrew GCC 9.3.0_1) 9.3.0
 - GNU Fortran (Homebrew GCC 8.4.0_1) 8.4.0
 - GNU Fortran (Homebrew GCC 9.3.0_1) 9.3.0
-- Node.js v12.18.1
+- Node.js v12.18.2
 - NVM 0.35.3
-- NVM - Cached node versions: v6.17.1 v8.17.0 v10.21.0 v12.18.1 v13.14.0 v14.4.0
+- NVM - Cached node versions: v6.17.1 v8.17.0 v10.21.0 v12.18.2 v13.14.0 v14.5.0
 - PowerShell 7.0.2
 - Python 2.7.17
 - Python 3.7.7
@@ -36,7 +36,7 @@
 - Bundler version 2.1.4
 - Carthage 0.35.0
 - CocoaPods 1.9.3
-- Homebrew 2.4.2
+- Homebrew 2.4.3
 - NPM 6.14.5
 - Yarn 1.22.4
 - NuGet 5.6.0.6489
@@ -47,10 +47,10 @@
 
 ### Project Management
 - Apache Maven 3.6.3
-- Gradle 6.5
+- Gradle 6.5.1
 
 ### Utilities
-- Curl 7.71.0
+- Curl 7.71.1
 - Git: 2.27.0
 - Git LFS: 2.11.0
 - GitHub CLI: 0.10.1
@@ -67,7 +67,7 @@
 - aria2 1.35.0
 - azcopy 10.4.3
 - zstd 1.4.5
-- bazel 3.3.0
+- bazel 3.3.1
 - bazelisk v1.5.0
 - helm v3.2.4+g0ad800e
 - virtualbox 6.1.10r138449
@@ -77,13 +77,13 @@
 - 7-Zip 16.02
 
 ### Tools
-- Fastlane 2.149.1
+- Fastlane 2.150.1
 - Cmake 3.17.3
-- App Center CLI 2.6.0
+- App Center CLI 2.6.1
 - Azure CLI 2.8.0
-- AWS CLI 2.0.25
+- AWS CLI 2.0.27
 - AWS SAM CLI 0.53.0
-- Aliyun CLI 3.0.48
+- Aliyun CLI 3.0.49
 - GHCup v0.1.5-p2
 - GHC 8.10.1
 - Cabal 3.2.0.0
@@ -94,9 +94,9 @@
 - SafariDriver 13.1.1 (15609.2.9.1.2)
 - Google Chrome 83.0.4103.116 
 - ChromeDriver 83.0.4103.39
-- Microsoft Edge 83.0.478.56 
-- MSEdgeDriver 83.0.478.56
-- Mozilla Firefox 77.0.1
+- Microsoft Edge 83.0.478.58 
+- MSEdgeDriver 83.0.478.58
+- Mozilla Firefox 78.0.1
 - geckodriver 0.26.0
 
 ### Cached Tools
@@ -109,8 +109,8 @@
 #### Python
 - 2.7.18
 - 3.5.9
-- 3.6.10
-- 3.7.7
+- 3.6.11
+- 3.7.8
 - 3.8.3
 
 #### PyPy
diff --git a/images/win/Windows2016-Azure.json b/images/win/Windows2016-Azure.json
index 05333241..349591cd 100644
--- a/images/win/Windows2016-Azure.json
+++ b/images/win/Windows2016-Azure.json
@@ -84,6 +84,11 @@
             "source": "{{ template_dir }}/scripts/SoftwareReport",
             "destination": "{{user `image_folder`}}"
         },
+        {
+            "type": "file",
+            "source": "{{ template_dir }}/scripts/Tests",
+            "destination": "{{user `image_folder`}}"
+        },
         {
             "type": "windows-shell",
             "inline": [
@@ -839,18 +844,6 @@
                 "{{ template_dir }}/scripts/Installers/Validate-AliyunCli.ps1"
             ]
         },
-        {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-JavaTools.ps1"
-            ]
-        },
-        {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-Cmake.ps1"
-            ]
-        },
         {
             "type": "powershell",
             "scripts":[
@@ -911,12 +904,6 @@
                 "{{ template_dir }}/scripts/Installers/Validate-AzureCosmosDbEmulator.ps1"
             ]
         },
-        {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-7zip.ps1"
-            ]
-        },
         {
             "type": "powershell",
             "scripts":[
@@ -983,18 +970,6 @@
                 "{{ template_dir }}/scripts/Installers/Validate-KubernetesCli.ps1"
             ]
         },
-        {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-Kind.ps1"
-            ]
-        },
-        {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-MongoDB.ps1"
-            ]
-        },
         {
             "type": "powershell",
             "scripts":[
@@ -1019,6 +994,12 @@
             "type": "windows-restart",
             "restart_timeout": "10m"
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Tests/RunAll-Tests.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "inline": [
diff --git a/images/win/Windows2019-Azure.json b/images/win/Windows2019-Azure.json
index cf10a903..94a9a937 100644
--- a/images/win/Windows2019-Azure.json
+++ b/images/win/Windows2019-Azure.json
@@ -84,6 +84,11 @@
             "source": "{{ template_dir }}/scripts/SoftwareReport",
             "destination": "{{user `image_folder`}}"
         },
+        {
+            "type": "file",
+            "source": "{{ template_dir }}/scripts/Tests",
+            "destination": "{{user `image_folder`}}"
+        },
         {
             "type": "windows-shell",
             "inline": [
@@ -109,6 +114,14 @@
             ],
             "execution_policy": "unrestricted"
         },
+        {
+            "type": "powershell",
+            "elevated_user": "SYSTEM",
+            "elevated_password": "",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Windows2019/Install-WSL.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
@@ -243,6 +256,12 @@
                 "{{ template_dir }}/scripts/Installers/Validate-Wix.ps1"
             ]
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Installers/Validate-WSL.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "scripts":[
@@ -812,18 +831,6 @@
                 "{{ template_dir }}/scripts/Installers/Validate-NodeLts.ps1"
             ]
         },
-        {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-JavaTools.ps1"
-            ]
-        },
-        {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-Cmake.ps1"
-            ]
-        },
         {
             "type": "powershell",
             "scripts":[
@@ -885,12 +892,6 @@
             ]
         },
         {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-7zip.ps1"
-            ]
-        },
-         {
             "type": "powershell",
             "scripts":[
                 "{{ template_dir }}/scripts/Installers/Validate-Packer.ps1"
@@ -962,18 +963,6 @@
                 "{{ template_dir }}/scripts/Installers/Validate-KubernetesCli.ps1"
             ]
         },
-        {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-Kind.ps1"
-            ]
-        },
-        {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-MongoDB.ps1"
-            ]
-        },
         {
             "type": "powershell",
             "scripts":[
@@ -1010,6 +999,12 @@
             "type": "windows-restart",
             "restart_timeout": "10m"
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Tests/RunAll-Tests.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "inline": [
@@ -1062,4 +1057,4 @@
             ]
         }
     ]
-}
\ No newline at end of file
+}
diff --git a/images/win/scripts/ImageHelpers/ImageHelpers.psm1 b/images/win/scripts/ImageHelpers/ImageHelpers.psm1
index 95a7d6c7..d711f745 100644
--- a/images/win/scripts/ImageHelpers/ImageHelpers.psm1
+++ b/images/win/scripts/ImageHelpers/ImageHelpers.psm1
@@ -4,6 +4,7 @@ param()
 . $PSScriptRoot\PathHelpers.ps1
 . $PSScriptRoot\InstallHelpers.ps1
 . $PSScriptRoot\ChocoHelpers.ps1
+. $PSScriptRoot\TestsHelpers.ps1
 
 Export-ModuleMember -Function @(
     'Test-MachinePath'
@@ -28,4 +29,7 @@ Export-ModuleMember -Function @(
     'Test-IsWin16'
     'Choco-Install'
     'Extract-7Zip'
+    'Get-CommandResult'
+    'Get-EnvironmentVariable'
+    'Invoke-PesterTests'
 )
diff --git a/images/win/scripts/ImageHelpers/TestsHelpers.ps1 b/images/win/scripts/ImageHelpers/TestsHelpers.ps1
new file mode 100644
index 00000000..5cc69dec
--- /dev/null
+++ b/images/win/scripts/ImageHelpers/TestsHelpers.ps1
@@ -0,0 +1,96 @@
+function Get-CommandResult {
+    Param (
+        [Parameter(Mandatory)][string] $Command
+    )
+    # CMD trick to suppress and show error output because some commands write to stderr (for example, "python --version")
+    [string[]]$output = & $env:comspec /c "$Command 2>&1"
+    $exitCode = $LASTEXITCODE
+
+    return @{
+        Output = $output
+        ExitCode = $exitCode
+    }
+}
+
+# Gets value of environment variable by the name
+function Get-EnvironmentVariable($variable) {
+    return [System.Environment]::GetEnvironmentVariable($variable)
+}
+
+# Update environment variables without reboot
+function Update-Environment {
+    $variables = [Environment]::GetEnvironmentVariables("Machine")
+    $variables.Keys | ForEach-Object {
+        $key = $_
+        $value = $variables[$key]
+        Set-Item -Path "env:$key" -Value $value
+    }
+    # We need to refresh PATH the latest one because it could include other variables "%M2_HOME%/bin"
+    $env:PATH = [Environment]::GetEnvironmentVariable("PATH", "Machine")
+}
+
+# Run Pester tests for specific tool
+function Invoke-PesterTests {
+    Param(
+        [Parameter(Mandatory)][string] $TestFile,
+        [string] $TestName
+    )
+
+    $testPath = "C:\image\Tests\${TestFile}.Tests.ps1"
+    if (-not (Test-Path $testPath)) {
+        throw "Unable to find test file '$TestFile' on '$testPath'."
+    }
+
+    $configuration = [PesterConfiguration] @{
+        Run = @{ Path = $testPath; PassThru = $true }
+        Output = @{ Verbosity = "Detailed" }
+    }
+    if ($TestName) {
+        $configuration.Filter.FullName = $TestName
+    }
+
+    # Update environment variables without reboot
+    Update-Environment
+
+    # Switch ErrorActionPreference to Stop temporary to make sure that tests will on silent errors too
+    $backupErrorActionPreference = $ErrorActionPreference
+    $ErrorActionPreference = "Stop"
+    $results = Invoke-Pester -Configuration $configuration
+    $ErrorActionPreference = $backupErrorActionPreference
+
+    # Fail in case if no tests are run
+    if (-not ($results -and ($results.FailedCount -eq 0) -and ($results.PassedCount -gt 0))) {
+        $results
+        throw "Test run has failed"
+    }
+}
+
+# Pester Assert to check exit code of command
+function ShouldReturnZeroExitCode {
+    Param(
+        [String] $ActualValue,
+        [switch] $Negate,
+        [string] $Because
+    )
+
+    $result = Get-CommandResult $ActualValue
+
+    [bool]$succeeded = $result.ExitCode -eq 0
+    if ($Negate) { $succeeded = -not $succeeded }
+
+    if (-not $succeeded)
+    {
+        $сommandOutputIndent = " " * 4
+        $commandOutput = ($result.Output | ForEach-Object { "${сommandOutputIndent}${_}" }) -join "`n"
+        $failureMessage = "Command '${ActualValue}' has finished with exit code ${actualExitCode}`n${commandOutput}"
+    }
+
+    return [PSCustomObject] @{
+        Succeeded      = $succeeded
+        FailureMessage = $failureMessage
+    }
+}
+
+If (Get-Command -Name Add-AssertionOperator -ErrorAction SilentlyContinue) {
+    Add-AssertionOperator -Name ReturnZeroExitCode -InternalName ShouldReturnZeroExitCode -Test ${function:ShouldReturnZeroExitCode}
+}
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Install-7zip.ps1 b/images/win/scripts/Installers/Install-7zip.ps1
index 419c8178..9ad1e204 100644
--- a/images/win/scripts/Installers/Install-7zip.ps1
+++ b/images/win/scripts/Installers/Install-7zip.ps1
@@ -4,3 +4,5 @@
 ################################################################################
 
 Choco-Install -PackageName 7zip.install
+
+Invoke-PesterTests -TestFile "Tools" -TestName "7-Zip"
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Install-Cmake.ps1 b/images/win/scripts/Installers/Install-Cmake.ps1
index 37183d5e..8baa82e2 100644
--- a/images/win/scripts/Installers/Install-Cmake.ps1
+++ b/images/win/scripts/Installers/Install-Cmake.ps1
@@ -4,3 +4,5 @@
 ################################################################################
 
 Choco-Install -PackageName cmake.install -ArgumentList "--installargs",'ADD_CMAKE_TO_PATH=""System""'
+
+Invoke-PesterTests -TestFile "Tools" -TestName "CMake"
\ 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 49b95e3a..759d132f 100644
--- a/images/win/scripts/Installers/Install-JavaTools.ps1
+++ b/images/win/scripts/Installers/Install-JavaTools.ps1
@@ -126,3 +126,5 @@ $archivePath = Start-DownloadWithRetry -Url $uri -Name "cobertura.zip"
 Extract-7Zip -Path $archivePath -DestinationPath "C:\"
 
 setx COBERTURA_HOME $coberturaPath /M
+
+Invoke-PesterTests -TestFile "Java"
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Install-Kind.ps1 b/images/win/scripts/Installers/Install-Kind.ps1
index 0e97cc04..b1c936fc 100644
--- a/images/win/scripts/Installers/Install-Kind.ps1
+++ b/images/win/scripts/Installers/Install-Kind.ps1
@@ -38,3 +38,5 @@ catch
     Write-Host $_.Exception.Message
     exit 1
 }
+
+Invoke-PesterTests -TestFile "Tools" -TestName "Kind"
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Install-MongoDB.ps1 b/images/win/scripts/Installers/Install-MongoDB.ps1
index 245e5b98..177300e9 100644
--- a/images/win/scripts/Installers/Install-MongoDB.ps1
+++ b/images/win/scripts/Installers/Install-MongoDB.ps1
@@ -7,3 +7,5 @@ Choco-Install -PackageName mongodb
 $mongoPath = (Get-CimInstance Win32_Service -Filter "Name LIKE 'mongodb'").PathName
 $mongoBin = Split-Path -Path $mongoPath.split('"')[1]
 Add-MachinePathItem "$mongoBin"
+
+Invoke-PesterTests -TestFile "Databases" -TestName "MongoDB"
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Validate-Cmake.ps1 b/images/win/scripts/Installers/Validate-Cmake.ps1
deleted file mode 100644
index df683591..00000000
--- a/images/win/scripts/Installers/Validate-Cmake.ps1
+++ /dev/null
@@ -1,16 +0,0 @@
-################################################################################
-##  File:  Validate-Cmake.ps1
-##  Desc:  Validate Cmake
-################################################################################
-
-if(Get-Command -Name 'cmake')
-{
-    Write-Host "CMake $(cmake -version) on path"
-}
-else
-{
-    Write-Host "CMake not on path"
-    exit 1
-}
-
-
diff --git a/images/win/scripts/Installers/Validate-JavaTools.ps1 b/images/win/scripts/Installers/Validate-JavaTools.ps1
deleted file mode 100644
index 50513156..00000000
--- a/images/win/scripts/Installers/Validate-JavaTools.ps1
+++ /dev/null
@@ -1,79 +0,0 @@
-################################################################################
-##  File:  Validate-JavaTools.ps1
-##  Desc:  Validate various JDKs and java tools
-################################################################################
-
-Function Validate-JavaVersion {
-   param (
-      [Parameter(Mandatory)] [string] $Version,
-      [switch] $Default
-   )
-
-   Write-Host "Checking Java $version"
-
-   # Set Path to get Java
-   if (-not $Default)
-   {
-      # Take 7 & 8 for versions 1.7 and 1.8
-      $versionNumber = $version.Split(".") | Select-Object -Last 1
-
-      $javaPath = [System.Environment]::GetEnvironmentVariable("JAVA_HOME_${versionNumber}_X64")
-      if ([string]::IsNullOrEmpty($javaPath))
-      {
-         Write-Host "Environment variable 'JAVA_HOME_${versionNumber}_X64' is null"
-         exit 1
-      }
-
-      $javaBin = "$javaPath\bin;"
-      $env:Path = $javaBin + $env:Path
-   }
-   else
-   {
-      Validate-JavaVersion -Version $Version
-   }
-
-   $isJavaExists =  $($(& $env:comspec "/s /c java -version 2>&1") | Out-String) -match '^(?<vendor>.+) version "(?<version>.+)".*'
-
-   if ($isJavaExists)
-   {
-      $javaVersion = $matches.version
-   }
-   else
-   {
-      Write-Host "Java $version was not found"
-      exit 1
-   }
-
-   $isJavaCorrect = $javaVersion.StartsWith($version)
-
-   if($isJavaCorrect)
-   {
-      Write-Host "Java $javaVersion found"
-      # Reset Path to the default one in case we need to check the default Java later
-      $env:Path = [System.Environment]::GetEnvironmentVariable("Path","Machine") + ";" + [System.Environment]::GetEnvironmentVariable("Path","User")
-   }
-   else
-   {
-      Write-Host "Expected Java $version, but found $javaVersion"
-      exit 1
-   }
-}
-
-if((Get-Command -Name 'java') -and (Get-Command -Name 'mvn') -and (Get-Command -Name 'ant') -and (Get-Command -Name 'gradle'))
-{
-    Write-Host "Java $(java -version) on path"
-    Write-Host "Maven $(mvn -version) on path"
-    Write-Host "Ant $(ant -version) on path"
-    Write-Host "Gradle $(gradle -version) on path"
-}
-else
-{
-    Write-Host "one of Java,Maven,Ant,Gradle is not on path."
-    exit 1
-}
-
-Write-Host "Checking installed Java versions"
-Validate-JavaVersion -Version "1.7"
-Validate-JavaVersion -Version "1.8" -Default
-Validate-JavaVersion -Version "11"
-Validate-JavaVersion -Version "13"
diff --git a/images/win/scripts/Installers/Validate-Kind.ps1 b/images/win/scripts/Installers/Validate-Kind.ps1
deleted file mode 100644
index 9147f462..00000000
--- a/images/win/scripts/Installers/Validate-Kind.ps1
+++ /dev/null
@@ -1,14 +0,0 @@
-################################################################################
-##  File:  Validate-Kind.ps1
-##  Desc:  Validate Kind.
-################################################################################
-
-if (Get-Command -Name 'kind')
-{
-    Write-Host "kind $(kind version) in path"
-}
-else
-{
-    Write-Host "kind is not in path"
-    exit 1
-}
diff --git a/images/win/scripts/Installers/Validate-MongoDB.ps1 b/images/win/scripts/Installers/Validate-MongoDB.ps1
deleted file mode 100644
index 517f824c..00000000
--- a/images/win/scripts/Installers/Validate-MongoDB.ps1
+++ /dev/null
@@ -1,24 +0,0 @@
-################################################################################
-##  File:  Validate-MongoDB.ps1
-##  Desc:  Validate MongoDB
-################################################################################
-
-if (Get-Command -Name 'mongod')
-{
-    Write-Host 'mongod is on path'
-}
-else
-{
-    Write-Host 'mongod not on path'
-    exit 1
-}
-
-if (Get-Command -Name 'mongo')
-{
-    Write-Host 'mongo is on path'
-}
-else
-{
-    Write-Host 'mongo not on path'
-    exit 1
-}
diff --git a/images/win/scripts/Installers/Validate-7zip.ps1 b/images/win/scripts/Installers/Validate-WSL.ps1
similarity index 54%
rename from images/win/scripts/Installers/Validate-7zip.ps1
rename to images/win/scripts/Installers/Validate-WSL.ps1
index d29d394e..83da6933 100644
--- a/images/win/scripts/Installers/Validate-7zip.ps1
+++ b/images/win/scripts/Installers/Validate-WSL.ps1
@@ -1,15 +1,14 @@
 ################################################################################
-##  File:  Validate-7zip.ps1
-##  Desc:  Validate 7zip
+##  File:  Validate-WSL.ps1
+##  Desc:  Validate WSL CLI existst
 ################################################################################
 
-if (Get-Command -Name '7z')
+if (Get-Command -Name 'wsl')
 {
-    Write-Host '7zip on path'
+    Write-Host 'wsl is on path'
 }
 else
 {
-    Write-Host '7zip is not on path'
+    Write-Host 'wsl not on path'
     exit 1
 }
-
diff --git a/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1 b/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1
index 794c1b0f..5afc6e61 100644
--- a/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1
+++ b/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1
@@ -41,6 +41,8 @@ Install-PackageProvider -Name NuGet -MinimumVersion 2.8.5.201 -Force
 Install-Module -Name PowerShellGet -Force
 Set-PSRepository -InstallationPolicy Trusted -Name PSGallery
 
+Write-Host "Install the latest Pester version"
+Install-Module Pester -Scope AllUsers -SkipPublisherCheck -Force
 
 Write-Host "Disable Antivirus"
 Set-MpPreference -DisableRealtimeMonitoring $true
diff --git a/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1 b/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1
index 99c238e8..e57ccb98 100644
--- a/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1
+++ b/images/win/scripts/Installers/Windows2019/Initialize-VM.ps1
@@ -38,6 +38,8 @@ Install-PackageProvider -Name NuGet -MinimumVersion 2.8.5.201 -Force
 Install-Module -Name PowerShellGet -Force
 Set-PSRepository -InstallationPolicy Trusted -Name PSGallery
 
+Write-Host "Install the latest Pester version"
+Install-Module Pester -Scope AllUsers -SkipPublisherCheck -Force
 
 Write-Host "Disable Antivirus"
 Set-MpPreference -DisableRealtimeMonitoring $true
diff --git a/images/win/scripts/Installers/Windows2019/Install-WSL.ps1 b/images/win/scripts/Installers/Windows2019/Install-WSL.ps1
new file mode 100644
index 00000000..2e83a1b8
--- /dev/null
+++ b/images/win/scripts/Installers/Windows2019/Install-WSL.ps1
@@ -0,0 +1,8 @@
+################################################################################
+##  File:  Install-WSL.ps1
+##  Desc:  Install Windows Subsystem for Linux
+################################################################################
+
+Write-Host "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/SoftwareReport/SoftwareReport.Generator.ps1 b/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
index b1ba9152..0f7f1fa0 100644
--- a/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
+++ b/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
@@ -22,6 +22,11 @@ $markdown += New-MDList -Style Unordered -Lines @(
     "Image Version: $env:ImageVersion"
 )
 
+$markdown += New-MDHeader "Enabled windows optional features" -Level 2
+$markdown += New-MDList -Style Unordered -Lines @(
+    "Windows Subsystem for Linux"
+)
+
 $markdown += New-MDHeader "Installed Software" -Level 2
 $markdown += New-MDHeader "Language and Runtime" -Level 3
 
diff --git a/images/win/scripts/Tests/Databases.Tests.ps1 b/images/win/scripts/Tests/Databases.Tests.ps1
new file mode 100644
index 00000000..b7cda7a4
--- /dev/null
+++ b/images/win/scripts/Tests/Databases.Tests.ps1
@@ -0,0 +1,8 @@
+Describe "MongoDB" {
+    It "<ToolName>" -TestCases @(
+        @{ ToolName = "mongo" }
+        @{ ToolName = "mongod" }
+    ) {
+        "$ToolName --version" | Should -ReturnZeroExitCode
+    }
+}
\ No newline at end of file
diff --git a/images/win/scripts/Tests/Java.Tests.ps1 b/images/win/scripts/Tests/Java.Tests.ps1
new file mode 100644
index 00000000..9ca9be19
--- /dev/null
+++ b/images/win/scripts/Tests/Java.Tests.ps1
@@ -0,0 +1,36 @@
+Describe "Java" {
+    It "Java <DefaultJavaVersion> is default" -TestCases @(@{ DefaultJavaVersion = 8 }) {
+        $actualJavaPath = Get-EnvironmentVariable "JAVA_HOME"
+        $expectedJavaPath = Get-EnvironmentVariable "JAVA_HOME_${DefaultJavaVersion}_X64"
+
+        $actualJavaPath | Should -Not -BeNullOrEmpty
+        $expectedJavaPath | Should -Not -BeNullOrEmpty
+        $actualJavaPath | Should -Be $expectedJavaPath
+    }
+
+    It "<ToolName>" -TestCases @(
+        @{ ToolName = "java" }
+        @{ ToolName = "mvn" }
+        @{ ToolName = "ant" }
+        @{ ToolName = "gradle" }
+    ) {
+        "$ToolName -version" | Should -ReturnZeroExitCode
+    }
+
+    It "Java <Version>" -TestCases @(
+        @{ Version = "1.7" }
+        @{ Version = "1.8" }
+        @{ Version = "11" }
+        @{ Version = "13" }
+    ) {
+        $versionNumber = $version.Split(".") | Select-Object -Last 1
+
+        $javaVariableValue = Get-EnvironmentVariable "JAVA_HOME_${versionNumber}_X64"
+        $javaVariableValue | Should -Not -BeNullOrEmpty
+        $javaPath = Join-Path $javaVariableValue "bin\java"
+
+        $result = Get-CommandResult "`"$javaPath`" -version"
+        $result.ExitCode | Should -Be 0
+        $result.Output[0] | Should -Match ([regex]::Escape("openjdk version `"${Version}."))
+    }
+}
\ No newline at end of file
diff --git a/images/win/scripts/Tests/RunAll-Tests.ps1 b/images/win/scripts/Tests/RunAll-Tests.ps1
new file mode 100644
index 00000000..1d8e835c
--- /dev/null
+++ b/images/win/scripts/Tests/RunAll-Tests.ps1
@@ -0,0 +1 @@
+Invoke-PesterTests "*"
\ No newline at end of file
diff --git a/images/win/scripts/Tests/Tools.Tests.ps1 b/images/win/scripts/Tests/Tools.Tests.ps1
new file mode 100644
index 00000000..6ddbcb21
--- /dev/null
+++ b/images/win/scripts/Tests/Tools.Tests.ps1
@@ -0,0 +1,17 @@
+Describe "7-Zip" {
+    It "7z" {
+        "7z" | Should -ReturnZeroExitCode
+    }
+}
+
+Describe "CMake" {
+    It "cmake" {
+        "cmake --version" | Should -ReturnZeroExitCode
+    }
+}
+
+Describe "Kind" {
+    It "Kind" {
+        "kind version" | Should -ReturnZeroExitCode
+    }
+}
\ No newline at end of file