diff --git a/images/win/scripts/Installers/Install-OpenSSL.ps1 b/images/win/scripts/Installers/Install-OpenSSL.ps1
new file mode 100644
index 000000000..ee5f87fc6
--- /dev/null
+++ b/images/win/scripts/Installers/Install-OpenSSL.ps1
@@ -0,0 +1,40 @@
+################################################################################
+##  File:  Install-OpenSSL.ps1
+##  Desc:  Install win64-openssl.
+################################################################################
+
+$arch = "INTEL"
+$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 $installer
+}
+
+# Get installer of the latest version
+$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 $installerArgs
+
+# Update PATH
+Add-MachinePathItem "$installDir\bin"
+$env:Path = Get-MachinePath
+
+Invoke-PesterTests -TestFile "Tools" -TestName "OpenSSL"
diff --git a/images/win/scripts/Tests/ChocoPackages.Tests.ps1 b/images/win/scripts/Tests/ChocoPackages.Tests.ps1
index b6a168284..d0edb67bc 100644
--- a/images/win/scripts/Tests/ChocoPackages.Tests.ps1
+++ b/images/win/scripts/Tests/ChocoPackages.Tests.ps1
@@ -46,12 +46,6 @@ Describe "Nuget" {
     }
 }
 
-Describe "OpenSSL" {
-    It "OpenSSL" {
-       "openssl version" | Should -ReturnZeroExitCode
-    }
-}
-
 Describe "Packer" {
     It "Packer" {
        "packer --version" | Should -ReturnZeroExitCode
diff --git a/images/win/scripts/Tests/Tools.Tests.ps1 b/images/win/scripts/Tests/Tools.Tests.ps1
index 873a41613..26ec41976 100644
--- a/images/win/scripts/Tests/Tools.Tests.ps1
+++ b/images/win/scripts/Tests/Tools.Tests.ps1
@@ -223,3 +223,9 @@ Describe "SQL OLEDB Driver" {
         "HKLM:\SOFTWARE\Microsoft\MSOLEDBSQL" | Should -Exist
     }
 }
+
+Describe "OpenSSL" {
+    It "OpenSSL" {
+        "openssl version" | Should -ReturnZeroExitCode
+    }
+}
diff --git a/images/win/toolsets/toolset-2019.json b/images/win/toolsets/toolset-2019.json
index 4946a0e07..c4b65e076 100644
--- a/images/win/toolsets/toolset-2019.json
+++ b/images/win/toolsets/toolset-2019.json
@@ -454,10 +454,6 @@
             { "name": "innosetup" },
             { "name": "jq" },
             { "name": "NuGet.CommandLine" },
-            {
-                "name": "openssl.light",
-                "args": [ "--version=1.1.1.20181020" ]
-            },
             { "name": "packer" },
             { "name": "strawberryperl" },
             { "name": "pulumi" },
@@ -502,5 +498,8 @@
     "kotlin": {
         "version": "latest",
         "binary_name": "kotlin-compiler"
+    },
+    "openssl": {
+        "version": "1.1.1"
     }
 }
diff --git a/images/win/toolsets/toolset-2022.json b/images/win/toolsets/toolset-2022.json
index ed1b230e3..3c1d624fc 100644
--- a/images/win/toolsets/toolset-2022.json
+++ b/images/win/toolsets/toolset-2022.json
@@ -365,10 +365,6 @@
             { "name": "innosetup" },
             { "name": "jq" },
             { "name": "NuGet.CommandLine" },
-            {
-                "name": "openssl.light",
-                "args": [ "--version=1.1.1.20181020" ]
-            },
             { "name": "packer" },
             { "name": "strawberryperl" },
             { "name": "pulumi" },
@@ -413,5 +409,8 @@
     "kotlin": {
         "version": "latest",
         "binary_name": "kotlin-compiler"
+    },
+    "openssl": {
+        "version": "1.1.1"
     }
 }
diff --git a/images/win/windows2019.json b/images/win/windows2019.json
index 55eaeedb9..03e1a3648 100644
--- a/images/win/windows2019.json
+++ b/images/win/windows2019.json
@@ -185,7 +185,8 @@
                 "{{ template_dir }}/scripts/Installers/Install-AzureDevOpsCli.ps1",
                 "{{ template_dir }}/scripts/Installers/Install-CommonUtils.ps1",
                 "{{ template_dir }}/scripts/Installers/Install-JavaTools.ps1",
-                "{{ template_dir }}/scripts/Installers/Install-Kotlin.ps1"
+                "{{ template_dir }}/scripts/Installers/Install-Kotlin.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-OpenSSL.ps1"
             ]
         },
         {
diff --git a/images/win/windows2022.json b/images/win/windows2022.json
index c4dc8f646..2f5a05610 100644
--- a/images/win/windows2022.json
+++ b/images/win/windows2022.json
@@ -191,7 +191,8 @@
                 "{{ template_dir }}/scripts/Installers/Install-AzureDevOpsCli.ps1",
                 "{{ template_dir }}/scripts/Installers/Install-CommonUtils.ps1",
                 "{{ template_dir }}/scripts/Installers/Install-JavaTools.ps1",
-                "{{ template_dir }}/scripts/Installers/Install-Kotlin.ps1"
+                "{{ template_dir }}/scripts/Installers/Install-Kotlin.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-OpenSSL.ps1"
             ]
         },
         {