diff --git a/images/win/Windows2016-Azure.json b/images/win/Windows2016-Azure.json
index 05333241a..349591cd4 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 d5bf5f739..94a9a9375 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": [
@@ -826,18 +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":[
@@ -899,12 +892,6 @@
             ]
         },
         {
-            "type": "powershell",
-            "scripts":[
-                "{{ template_dir }}/scripts/Installers/Validate-7zip.ps1"
-            ]
-        },
-         {
             "type": "powershell",
             "scripts":[
                 "{{ template_dir }}/scripts/Installers/Validate-Packer.ps1"
@@ -976,18 +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":[
@@ -1024,6 +999,12 @@
             "type": "windows-restart",
             "restart_timeout": "10m"
         },
+        {
+            "type": "powershell",
+            "scripts":[
+                "{{ template_dir }}/scripts/Tests/RunAll-Tests.ps1"
+            ]
+        },
         {
             "type": "powershell",
             "inline": [
diff --git a/images/win/scripts/ImageHelpers/ImageHelpers.psm1 b/images/win/scripts/ImageHelpers/ImageHelpers.psm1
index 95a7d6c70..da1449568 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 +29,8 @@ Export-ModuleMember -Function @(
     'Test-IsWin16'
     'Choco-Install'
     'Extract-7Zip'
+    'Get-CommandResult'
+    'Get-WhichTool'
+    '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 000000000..fdc341ccf
--- /dev/null
+++ b/images/win/scripts/ImageHelpers/TestsHelpers.ps1
@@ -0,0 +1,106 @@
+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 path to the tool, analogue of 'which tool'
+function Get-WhichTool {
+    Param (
+        [Parameter(Mandatory)][string] $Tool
+    )
+    return (Get-Command $Tool).Path
+}
+
+# Gets value of environment variable by the name
+function Get-EnvironmentVariable($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))) {
+        $results
+        throw "Test run has finished with errors"
+    }
+}
+
+# Pester Assert to check exit code of command
+function ShouldReturnZeroExitCode {
+    Param(
+        [String]$ActualValue,
+        [switch]$Negate,
+        [string] $Because
+    )
+
+    $result = Get-CommandResult $ActualValue
+
+    [bool]$succeeded = $result.ExitCode -eq 0
+    if ($Negate) { $succeeded = -not $succeeded }
+
+
+
+    if (-not $succeeded)
+    {
+        $CommandResultIndent = " " * 4
+        $commandOutput = ($result.Output | ForEach-Object { "${CommandResultIndent}${_}" }) -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 419c81782..9ad1e2045 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 37183d5e6..8baa82e2a 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 49b95e3af..759d132fc 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-MongoDB.ps1 b/images/win/scripts/Installers/Install-MongoDB.ps1
index 245e5b98f..177300e97 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-7zip.ps1 b/images/win/scripts/Installers/Validate-7zip.ps1
deleted file mode 100644
index d29d394e1..000000000
--- a/images/win/scripts/Installers/Validate-7zip.ps1
+++ /dev/null
@@ -1,15 +0,0 @@
-################################################################################
-##  File:  Validate-7zip.ps1
-##  Desc:  Validate 7zip
-################################################################################
-
-if (Get-Command -Name '7z')
-{
-    Write-Host '7zip on path'
-}
-else
-{
-    Write-Host '7zip is not on path'
-    exit 1
-}
-
diff --git a/images/win/scripts/Installers/Validate-Cmake.ps1 b/images/win/scripts/Installers/Validate-Cmake.ps1
deleted file mode 100644
index df6835919..000000000
--- 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 50513156f..000000000
--- 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 9147f4621..000000000
--- 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 517f824cb..000000000
--- 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/Windows2016/Initialize-VM.ps1 b/images/win/scripts/Installers/Windows2016/Initialize-VM.ps1
index 794c1b0f6..5afc6e61f 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 99c238e8c..e57ccb981 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 $true
diff --git a/images/win/scripts/Tests/Databases.Tests.ps1 b/images/win/scripts/Tests/Databases.Tests.ps1
new file mode 100644
index 000000000..b7cda7a49
--- /dev/null
+++ b/images/win/scripts/Tests/Databases.Tests.ps1
@@ -0,0 +1,8 @@
+Describe "MongoDB" {
+    It "<ToolName>" -TestCases @(
+        @{ ToolName = "mongo" }
+        @{ ToolName = "mongod" }
+    ) {
+        "$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 000000000..04a749bd4
--- /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 000000000..1d8e835ca
--- /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 000000000..6ddbcb217
--- /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