diff --git a/images/win/scripts/ImageHelpers/TestsHelpers.ps1 b/images/win/scripts/ImageHelpers/TestsHelpers.ps1
index 7a0229ac5..ae3e10746 100644
--- a/images/win/scripts/ImageHelpers/TestsHelpers.ps1
+++ b/images/win/scripts/ImageHelpers/TestsHelpers.ps1
@@ -91,6 +91,39 @@ function ShouldReturnZeroExitCode {
     }
 }
 
+# Pester Assert to match output of command
+function ShouldMatchCommandOutput {
+    Param(
+        [String] $ActualValue,
+        [String] $RegularExpression,
+        [switch] $Negate
+    )
+
+    $output = (Get-CommandResult $ActualValue).Output | Out-String
+    [bool] $succeeded = $output -cmatch $RegularExpression
+
+    if ($Negate) {
+        $succeeded = -not $succeeded
+    }
+
+    $failureMessage = ''
+
+    if (-not $succeeded) {
+        if ($Negate) {
+            $failureMessage = "Expected regular expression '$RegularExpression' for '$ActualValue' command to not match '$output',but it did match."
+        }
+        else {
+            $failureMessage = "Expected regular expression '$RegularExpression' for '$ActualValue' command to match '$output',but it did not match."
+        }
+    }
+
+    return [PSCustomObject] @{
+        Succeeded      = $succeeded
+        FailureMessage = $failureMessage
+    }
+}
+
 If (Get-Command -Name Add-AssertionOperator -ErrorAction SilentlyContinue) {
     Add-AssertionOperator -Name ReturnZeroExitCode -InternalName ShouldReturnZeroExitCode -Test ${function:ShouldReturnZeroExitCode}
+    Add-AssertionOperator -Name MatchCommandOutput -InternalName ShouldMatchCommandOutput -Test ${function:ShouldMatchCommandOutput}
 }
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Install-Git.ps1 b/images/win/scripts/Installers/Install-Git.ps1
index 1537be801..25ce857db 100644
--- a/images/win/scripts/Installers/Install-Git.ps1
+++ b/images/win/scripts/Installers/Install-Git.ps1
@@ -41,3 +41,4 @@ Choco-Install -PackageName hub
 Add-MachinePathItem "C:\Program Files\Git\bin"
 
 Invoke-PesterTests -TestFile "Git" -TestName "Git"
+Invoke-PesterTests -TestFile "Git" -TestName "Hub"
diff --git a/images/win/scripts/Tests/Haskell.Tests.ps1 b/images/win/scripts/Tests/Haskell.Tests.ps1
index 99780a55f..b6ebb7630 100644
--- a/images/win/scripts/Tests/Haskell.Tests.ps1
+++ b/images/win/scripts/Tests/Haskell.Tests.ps1
@@ -17,11 +17,11 @@ Describe "Haskell" {
     }
 
     It "GHC <ghcVersion> is installed" -TestCases $ghcTestCases {
-        & $binGhcPath --version | Should -Match $ghcVersion
+        "$binGhcPath --version" | Should -MatchCommandOutput $ghcVersion
     }
 
     It "GHC <defaultGhcVersion> is the default version and should be the latest installed" -TestCases @{defaultGhcVersion = $defaultGhcVersion} {
-        ghc --version | Should -Match $defaultGhcVersion
+        "ghc --version" | Should -MatchCommandOutput $defaultGhcVersion
     }
 
     It "Cabal is installed" {