diff --git a/images/linux/scripts/installers/Configure-Toolset.ps1 b/images/linux/scripts/installers/Configure-Toolset.ps1
index 4a145a5d5..1b30dad30 100644
--- a/images/linux/scripts/installers/Configure-Toolset.ps1
+++ b/images/linux/scripts/installers/Configure-Toolset.ps1
@@ -4,6 +4,8 @@
 ##  Desc:  Configure toolset
 ################################################################################
 
+Import-Module "$env:HELPER_SCRIPTS/Tests.Helpers.psm1" -DisableNameChecking
+
 function Get-ToolsetToolFullPath
 {
     param
@@ -93,3 +95,5 @@ foreach ($tool in $toolset.toolcache)
         Invoke-Expression -Command $command
     }
 }
+
+Invoke-PesterTests -TestFile "Toolset" -TestName "Toolset"
\ No newline at end of file
diff --git a/images/linux/scripts/installers/Validate-Toolset.ps1 b/images/linux/scripts/installers/Validate-Toolset.ps1
deleted file mode 100644
index de53f1ddd..000000000
--- a/images/linux/scripts/installers/Validate-Toolset.ps1
+++ /dev/null
@@ -1,92 +0,0 @@
-################################################################################
-##  File:  Validate-Toolset.ps1
-##  Team:  CI-Build
-##  Desc:  Validate Toolset
-################################################################################
-
-function Run-ExecutableTests {
-    param (
-        [Parameter(Mandatory)] [string[]] $Executables,
-        [Parameter(Mandatory)] [string] $ToolPath
-    )
-    $versionCommand = $Executables["command"]
-
-    foreach ($executable in $Executables["tools"]) {
-        $executablePath = Join-Path $ToolPath $executable
-        Write-Host "Check $executable..."
-        if (Test-Path $executablePath) {
-            Write-Host "$executable is successfully installed: $(& $executablePath $versionCommand)"
-        } else {
-            Write-Host "$executablePath is not installed!"
-            exit 1
-        }
-    }
-}
-
-$ErrorActionPreference = "Stop"
-
-# Define executables for cached tools
-$toolsExecutables = @{
-    Python = @{
-        tools = @("python", "bin/pip")
-        command = "--version"
-    }
-    node = @{
-        tools = @("bin/node", "bin/npm")
-        command = "--version"
-    }
-    PyPy = @{
-        tools = @("bin/python", "bin/pip")
-        command = "--version"
-    }
-    go = @{
-        tools = @("bin/go")
-        command = "version"
-    }
-    Ruby = @{
-        tools = @("bin/ruby")
-        command = "--version"
-    }
-}
-
-# Get toolset content
-$toolset = Get-Content -Path "$env:INSTALLER_SCRIPT_FOLDER/toolset.json" -Raw
-$tools = ConvertFrom-Json -InputObject $toolset | Select-Object -ExpandProperty toolcache
-
-foreach($tool in $tools) {
-
-    $toolPath = Join-Path $env:AGENT_TOOLSDIRECTORY $tool.name
-    # Get executables for current tool
-    $toolExecs = $toolsExecutables[$tool.name]
-
-    foreach ($version in $tool.versions) {
-        # Add wildcard if missing
-        if ($version.Split(".").Length -lt 3) {
-            $version += ".*"
-        }
-
-        # 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 $tool.arch
-
-        if ($toolExecs) {
-            Write-Host "Run validation test for $($tool.name)($($tool.arch)) $($foundVersion.name) executables..."
-            Run-ExecutableTests -Executables $toolExecs -ToolPath $foundVersionPath
-        }
-        $foundVersionName = $foundVersion.name
-        if ($tool.name -eq 'PyPy')
-        {
-            $pypyVersion = & "$foundVersionPath/bin/python" -c "import sys;print(sys.version.split('\n')[1])"
-            $foundVersionName = "{0} {1}" -f $foundVersionName, $pypyVersion
-        }
-    }
-}
\ No newline at end of file
diff --git a/images/linux/scripts/tests/Toolset.Tests.ps1 b/images/linux/scripts/tests/Toolset.Tests.ps1
new file mode 100644
index 000000000..c3d51704b
--- /dev/null
+++ b/images/linux/scripts/tests/Toolset.Tests.ps1
@@ -0,0 +1,62 @@
+Describe "Toolset" {
+    $tools = (Get-ToolsetContent).toolcache
+
+    $toolsExecutables = @{
+        Python = @{
+            tools = @("python", "bin/pip")
+            command = "--version"
+        }
+        node = @{
+            tools = @("bin/node", "bin/npm")
+            command = "--version"
+        }
+        PyPy = @{
+            tools = @("bin/python", "bin/pip")
+            command = "--version"
+        }
+        go = @{
+            tools = @("bin/go")
+            command = "version"
+        }
+        Ruby = @{
+            tools = @("bin/ruby")
+            command = "--version"
+        }
+    }
+
+    foreach($tool in $tools) {
+        $toolName = $tool.Name
+        Context "$toolName" {
+            $toolExecs = $toolsExecutables[$toolName]
+
+            foreach ($version in $tool.versions) {
+                # Add wildcard if missing
+                if ($version.Split(".").Length -lt 3) {
+                    $version += ".*"
+                }
+
+                $expectedVersionPath = Join-Path $env:AGENT_TOOLSDIRECTORY $toolName $version
+
+                It "$version version folder exists" -TestCases @{ ExpectedVersionPath = $expectedVersionPath} {
+                    $ExpectedVersionPath | Should -Exist
+                }
+
+                $toolExecs = $toolsExecutables[$toolName]
+                $foundVersion = Get-Item $expectedVersionPath `
+                    | Sort-Object -Property {[version]$_.name} -Descending `
+                    | Select-Object -First 1
+                $foundVersionPath = Join-Path $foundVersion $tool.arch
+
+                if($toolExecs) {
+                    foreach ($executable in $toolExecs["tools"]) {
+                        $executablePath = Join-Path $foundVersionPath $executable   
+    
+                        It "Validate $executable" -TestCases @{ExecutablePath = $executablePath} {
+                            $ExecutablePath | Should -Exist
+                        }
+                    }
+                }
+            }
+        }
+    }
+}
\ No newline at end of file
diff --git a/images/linux/ubuntu1604.json b/images/linux/ubuntu1604.json
index e30f30105..08e56cfca 100644
--- a/images/linux/ubuntu1604.json
+++ b/images/linux/ubuntu1604.json
@@ -246,8 +246,7 @@
             "type": "shell",
             "scripts": [
                 "{{template_dir}}/scripts/installers/Install-Toolset.ps1",
-                "{{template_dir}}/scripts/installers/Configure-Toolset.ps1",
-                "{{template_dir}}/scripts/installers/Validate-Toolset.ps1"
+                "{{template_dir}}/scripts/installers/Configure-Toolset.ps1"
             ],
             "environment_vars": [
                 "HELPER_SCRIPTS={{user `helper_script_folder`}}",
diff --git a/images/linux/ubuntu1804.json b/images/linux/ubuntu1804.json
index f1ffce716..b2fe43607 100644
--- a/images/linux/ubuntu1804.json
+++ b/images/linux/ubuntu1804.json
@@ -250,8 +250,7 @@
             "type": "shell",
             "scripts": [
                 "{{template_dir}}/scripts/installers/Install-Toolset.ps1",
-                "{{template_dir}}/scripts/installers/Configure-Toolset.ps1",
-                "{{template_dir}}/scripts/installers/Validate-Toolset.ps1"
+                "{{template_dir}}/scripts/installers/Configure-Toolset.ps1"
             ],
             "environment_vars": [
                 "HELPER_SCRIPTS={{user `helper_script_folder`}}",
diff --git a/images/linux/ubuntu2004.json b/images/linux/ubuntu2004.json
index a273d884f..f9b00f8e7 100644
--- a/images/linux/ubuntu2004.json
+++ b/images/linux/ubuntu2004.json
@@ -250,8 +250,7 @@
             "type": "shell",
             "scripts": [
                 "{{template_dir}}/scripts/installers/Install-Toolset.ps1",
-                "{{template_dir}}/scripts/installers/Configure-Toolset.ps1",
-                "{{template_dir}}/scripts/installers/Validate-Toolset.ps1"
+                "{{template_dir}}/scripts/installers/Configure-Toolset.ps1"
             ],
             "environment_vars": [
                 "HELPER_SCRIPTS={{user `helper_script_folder`}}",