diff --git a/images/win/scripts/Installers/Install-OpenSSL.ps1 b/images/win/scripts/Installers/Install-OpenSSL.ps1
index ee5f87fc6..2655ecc8d 100644
--- a/images/win/scripts/Installers/Install-OpenSSL.ps1
+++ b/images/win/scripts/Installers/Install-OpenSSL.ps1
@@ -1,38 +1,51 @@
 ################################################################################
 ##  File:  Install-OpenSSL.ps1
 ##  Desc:  Install win64-openssl.
+##  Supply chain security: checksum validation
 ################################################################################
 
-$arch = "INTEL"
-$bits = "64"
-$light = $false
+$arch = 'INTEL'
+$bits = '64'
+$light = 'false'
 $installer = "exe"
 $version = (Get-ToolsetContent).openssl.version
 $installDir = "$Env:ProgramFiles\OpenSSL"
 
 # Fetch available installers list
 $jsonUrl = 'https://raw.githubusercontent.com/slproweb/opensslhashes/master/win32_openssl_hashes.json'
-$installersAvailable = @()
-(Invoke-RestMethod $jsonUrl).files.PSObject.Properties |
-Where-Object MemberType -Eq NoteProperty |
-ForEach-Object { $installersAvailable += $_.Value }
 
-# Select appropriate installers
-$installersMatching = $installersAvailable | Where-Object {
-  ($_.basever -Eq $version -Or $_.basever -Like "$version.*") -And $_.arch -Eq $arch -And $_.bits -Eq $bits -And $_.light -Eq $light -And $_.installer -Eq $installer
+$installersAvailable = (Invoke-RestMethod $jsonUrl).files
+
+$distributor_file_hash = $null
+$installerUrl = $null
+$installerName = $null
+
+$installersAvailable | Get-Member -MemberType NoteProperty | ForEach-Object {
+  $key = $_.Name
+  if(($installersAvailable.$key.light -eq $light) -and ($installersAvailable.$key.arch -eq $arch) -and ($installersAvailable.$key.bits -eq $bits) -and ($installersAvailable.$key.installer -eq $installer) -and ($installersAvailable.$key.basever -eq $version)) {
+    $installerUrl = $installersAvailable.$key.url
+    $installerName = $key
+    $distributor_file_hash = $installersAvailable.$key.sha512
+    Break;
+  }
 }
 
-# Get installer of the latest version
-$latestInstaller = $installersMatching |
-Sort-Object { [version]$_.basever }, subver | 
-Select-Object -Last 1
-
 # Invoke installation
-$installerUrl = $latestInstaller.url
-$installerName = "openssl-$($latestInstaller.basever)$($latestInstaller.subver)-setup.$($latestInstaller.installer)"
+
 $installerArgs = '/silent', '/sp-', '/suppressmsgboxes', "/DIR=`"$installDir`""
 Install-Binary -Url "$installerUrl" -Name "$installerName" -ArgumentList $installerArgs
 
+#region Supply chain security
+Write-Verbose "Performing checksum verification"
+$local_file_hash = (Get-FileHash -Path (Join-Path ${env:TEMP} $installerName) -Algorithm SHA512).Hash
+
+if ($local_file_hash -ne $distributor_file_hash) {
+        Write-Host "hash must be equal to: ${distributor_file_hash}"
+        Write-Host "actual hash is: ${local_file_hash}"
+        throw 'Checksum verification failed, please rerun install'
+}
+#endregion
+
 # Update PATH
 Add-MachinePathItem "$installDir\bin"
 $env:Path = Get-MachinePath