diff --git a/contrib/win32/openssh/OpenSSHTestHelper.psm1 b/contrib/win32/openssh/OpenSSHTestHelper.psm1
index 731bb9810..422ebf883 100644
--- a/contrib/win32/openssh/OpenSSHTestHelper.psm1
+++ b/contrib/win32/openssh/OpenSSHTestHelper.psm1
@@ -20,6 +20,7 @@ $Script:UnitTestResultsFile = Join-Path $TestDataPath $UnitTestResultsFileName
 $Script:TestSetupLogFile = Join-Path $TestDataPath $TestSetupLogFileName
 $Script:E2ETestDirectory = Join-Path $repositoryRoot.FullName -ChildPath "regress\pesterTests"
 $Script:WindowsInBox = $false
+$Script:UseLibreSSL = $true
 $Script:EnableAppVerifier = $true
 $Script:PostmortemDebugging = $false
 
@@ -37,7 +38,8 @@ function Set-OpenSSHTestEnvironment
         [string] $TestDataPath = "$env:SystemDrive\OpenSSHTests",        
         [Boolean] $DebugMode = $false,
         [Switch] $NoAppVerifier,
-        [Switch] $PostmortemDebugging
+        [Switch] $PostmortemDebugging,
+        [Switch] $NoLibreSSL
     )
     
     if($PSBoundParameters.ContainsKey("Verbose"))
@@ -56,6 +58,7 @@ function Set-OpenSSHTestEnvironment
     $Script:TestSetupLogFile = Join-Path $TestDataPath "TestSetupLog.txt"
     $Script:UnitTestDirectory = Get-UnitTestDirectory
     $Script:EnableAppVerifier = -not ($NoAppVerifier.IsPresent)
+    $Script:UseLibreSSL = -not ($NoLibreSSL.IsPresent)
     if($Script:EnableAppVerifier)
     {
         $Script:PostmortemDebugging = $PostmortemDebugging.IsPresent
@@ -77,6 +80,7 @@ function Set-OpenSSHTestEnvironment
         "DebugMode" = $DebugMode                               # run openssh E2E in debug mode
         "EnableAppVerifier" = $Script:EnableAppVerifier
         "PostmortemDebugging" = $Script:PostmortemDebugging
+        "UseLibreSSL" = $Script:UseLibreSSL
         }
         
     #if user does not set path, pick it up
@@ -301,7 +305,8 @@ function Get-LocalUserProfile
 <#
       .SYNOPSIS
       This function installs the tools required by our tests
-      1) Pester for running the tests  
+      1) Pester for running the tests
+      2) Windbg for postmortem debugging
 #>
 function Install-OpenSSHTestDependencies
 {
@@ -594,7 +599,7 @@ function Invoke-OpenSSHE2ETest
     # Discover all CI tests and run them.
     Import-Module pester -force -global
     Push-Location $Script:E2ETestDirectory
-    Write-Log -Message "Running OpenSSH E2E tests..."    
+    Write-Log -Message "Running OpenSSH E2E tests..."
     $testFolders = @(Get-ChildItem *.tests.ps1 -Recurse | ForEach-Object{ Split-Path $_.FullName} | Sort-Object -Unique)
     Invoke-Pester $testFolders -OutputFormat NUnitXml -OutputFile $Script:E2ETestResultsFile -Tag $pri -PassThru
     Pop-Location
diff --git a/regress/pesterTests/KeyUtils.Tests.ps1 b/regress/pesterTests/KeyUtils.Tests.ps1
index a68c55e3b..bdc59302a 100644
--- a/regress/pesterTests/KeyUtils.Tests.ps1
+++ b/regress/pesterTests/KeyUtils.Tests.ps1
@@ -18,8 +18,8 @@ Describe "E2E scenarios for ssh key management" -Tags "CI" {
         }
 
         $keypassphrase = "testpassword"
-        $WindowsInBox = $OpenSSHTestInfo["WindowsInBox"]
-        if($WindowsInBox)
+        $UseLibreSSL = $OpenSSHTestInfo["UseLibreSSL"]
+        if($UseLibreSSL)
         {
             $keytypes = @("ed25519")                
         }
@@ -139,7 +139,7 @@ Describe "E2E scenarios for ssh key management" -Tags "CI" {
             {
                 $keyPath = Join-Path $testDir "id_$type"
                 remove-item $keyPath -ErrorAction SilentlyContinue
-                if($OpenSSHTestInfo["WindowsInBox"])
+                if($OpenSSHTestInfo["UseLibreSSL"])
                 {
                     ssh-keygen -t $type -P $keypassphrase -f $keyPath -Z aes128-ctr
                 }
@@ -252,7 +252,7 @@ Describe "E2E scenarios for ssh key management" -Tags "CI" {
             $keyFileName = "sshadd_userPermTestkey_ed25519"
             $keyFilePath = Join-Path $testDir $keyFileName
             Remove-Item -path "$keyFilePath*" -Force -ErrorAction SilentlyContinue
-            if($OpenSSHTestInfo["WindowsInBox"])
+            if($OpenSSHTestInfo["UseLibreSSL"])
             {
                 ssh-keygen.exe -t ed25519 -f $keyFilePath -P $keypassphrase -Z aes128-ctr
             }
@@ -377,23 +377,23 @@ Describe "E2E scenarios for ssh key management" -Tags "CI" {
         }
         AfterAll{$tC++}
 
-		It "$tC.$tI - ssh-keyscan with default arguments" -Skip:$WindowsInBox {
+		It "$tC.$tI - ssh-keyscan with default arguments" -Skip:$UseLibreSSL {
 			cmd /c "ssh-keyscan -p $port 127.0.0.1 2>&1 > $outputFile"
 			$outputFile | Should Contain '.*ssh-rsa.*'
 		}
 
-        It "$tC.$tI - ssh-keyscan with -p" -Skip:$WindowsInBox {
+        It "$tC.$tI - ssh-keyscan with -p" -Skip:$UseLibreSSL {
 			cmd /c "ssh-keyscan -p $port 127.0.0.1 2>&1 > $outputFile"
 			$outputFile | Should Contain '.*ssh-rsa.*'
 		}
 
-		It "$tC.$tI - ssh-keyscan with -f" -Skip:$WindowsInBox {
+		It "$tC.$tI - ssh-keyscan with -f" -Skip:$UseLibreSSL {
 			Set-Content -Path tmp.txt -Value "127.0.0.1"
 			cmd /c "ssh-keyscan -p $port -f tmp.txt 2>&1 > $outputFile"
 			$outputFile | Should Contain '.*ssh-rsa.*'
 		}
 
-		It "$tC.$tI - ssh-keyscan with -f -t" -Skip:$WindowsInBox {
+		It "$tC.$tI - ssh-keyscan with -f -t" -Skip:$UseLibreSSL {
 			Set-Content -Path tmp.txt -Value "127.0.0.1"
 			cmd /c "ssh-keyscan -p $port -f tmp.txt -t rsa,dsa 2>&1 > $outputFile"
 			$outputFile | Should Contain '.*ssh-rsa.*'
diff --git a/regress/pesterTests/Userkey_fileperm.Tests.ps1 b/regress/pesterTests/Userkey_fileperm.Tests.ps1
index 0ea561d2f..16aac1af3 100644
--- a/regress/pesterTests/Userkey_fileperm.Tests.ps1
+++ b/regress/pesterTests/Userkey_fileperm.Tests.ps1
@@ -50,7 +50,7 @@ Describe "Tests for user Key file permission" -Tags "CI" {
             $keyFileName = "sshtest_userPermTestkey_ed25519"
             $keyFilePath = Join-Path $testDir $keyFileName
             Remove-Item -path "$keyFilePath*" -Force -ErrorAction SilentlyContinue
-            if($OpenSSHTestInfo["WindowsInBox"])
+            if($OpenSSHTestInfo["UseLibreSSL"])
             {
                     ssh-keygen.exe -t ed25519 -f $keyFilePath -P $keypassphrase -Z aes128-ctr
             }