diff --git a/images/win/Windows2016-Azure.json b/images/win/Windows2016-Azure.json
index fa1352c8..442218d3 100644
--- a/images/win/Windows2016-Azure.json
+++ b/images/win/Windows2016-Azure.json
@@ -325,7 +325,9 @@
             "type": "powershell",
             "scripts":[
                 "{{ template_dir }}/scripts/Installers/Install-WindowsUpdates.ps1",
-                "{{ template_dir }}/scripts/Installers/Configure-DynamicPort.ps1"
+                "{{ template_dir }}/scripts/Installers/Configure-DynamicPort.ps1",
+                "{{ template_dir }}/scripts/Installers/Disable-JITDebugger.ps1",
+                "{{ template_dir }}/scripts/Installers/Configure-Shell.ps1"
             ],
             "elevated_user": "{{user `install_user`}}",
             "elevated_password": "{{user `install_password`}}"
@@ -383,9 +385,7 @@
         {
             "type": "powershell",
             "scripts":[
-                "{{ template_dir }}/scripts/Installers/Configure-Antivirus.ps1",
-                "{{ template_dir }}/scripts/Installers/Disable-JITDebugger.ps1",
-                "{{ template_dir }}/scripts/Installers/Post-Deployment.ps1"
+                "{{ template_dir }}/scripts/Installers/Configure-Antivirus.ps1"
             ]
         },
         {
diff --git a/images/win/Windows2019-Azure.json b/images/win/Windows2019-Azure.json
index 351ea5b7..0e3d180b 100644
--- a/images/win/Windows2019-Azure.json
+++ b/images/win/Windows2019-Azure.json
@@ -324,7 +324,9 @@
             "type": "powershell",
             "scripts":[
                 "{{ template_dir }}/scripts/Installers/Install-WindowsUpdates.ps1",
-                "{{ template_dir }}/scripts/Installers/Configure-DynamicPort.ps1"
+                "{{ template_dir }}/scripts/Installers/Configure-DynamicPort.ps1",
+                "{{ template_dir }}/scripts/Installers/Disable-JITDebugger.ps1",
+                "{{ template_dir }}/scripts/Installers/Configure-Shell.ps1"
             ],
             "elevated_user": "{{user `install_user`}}",
             "elevated_password": "{{user `install_password`}}"
@@ -383,9 +385,7 @@
             "type": "powershell",
             "scripts":[
                 "{{ template_dir }}/scripts/Installers/Configure-Antivirus.ps1",
-                "{{ template_dir }}/scripts/Installers/Disable-JITDebugger.ps1",
-                "{{ template_dir }}/scripts/Installers/Run-NGen.ps1",
-                "{{ template_dir }}/scripts/Installers/Post-Deployment.ps1"
+                "{{ template_dir }}/scripts/Installers/Run-NGen.ps1"
             ]
         },
         {
diff --git a/images/win/scripts/Installers/Configure-Shell.ps1 b/images/win/scripts/Installers/Configure-Shell.ps1
new file mode 100644
index 00000000..6bb7bc50
--- /dev/null
+++ b/images/win/scripts/Installers/Configure-Shell.ps1
@@ -0,0 +1,19 @@
+# Create shells folder
+$shellPath = "C:\shells"
+New-Item -Path $shellPath -ItemType Directory | Out-Null
+
+# sh and bash <--> C:\msys64\usr\bin\bash.exe
+New-Item -ItemType SymbolicLink -Path "$shellPath\bash.exe" -Target "C:\msys64\usr\bin\bash.exe" | Out-Null
+New-Item -ItemType SymbolicLink -Path "$shellPath\sh.exe" -Target "C:\msys64\usr\bin\sh.exe" | Out-Null
+
+# winbash <--> C:\Windows\System32\bash.exe
+New-Item -ItemType SymbolicLink -Path "$shellPath\winbash.exe" -Target "$env:SystemRoot\System32\bash.exe" | Out-Null
+
+# git4bash <--> C:\Program Files\Git\bin\bash.exe
+New-Item -ItemType SymbolicLink -Path "$shellPath\git4bash.exe" -Target "$env:ProgramFiles\Git\bin\bash.exe" | Out-Null
+
+# MSYS2 <--> C:\msys64\usr\bin\bash.exe
+New-Item -ItemType SymbolicLink -Path "$shellPath\msys2.exe" -Target "C:\msys64\usr\bin\bash.exe" | Out-Null
+
+# Add shells to PATH
+Add-MachinePathItem $shellPath
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Post-Deployment.ps1 b/images/win/scripts/Installers/Post-Deployment.ps1
deleted file mode 100644
index c514800d..00000000
--- a/images/win/scripts/Installers/Post-Deployment.ps1
+++ /dev/null
@@ -1,19 +0,0 @@
-# Create shells folder
-$shellPath = "C:\shells"
-$null = New-Item -Path $shellPath -ItemType Directory
-
-# MSYS2 <--> C:\msys64\usr\bin\bash.exe
-$null = New-Item -ItemType SymbolicLink -Path "$shellPath\msys2.exe" -Target "C:\msys64\usr\bin\bash.exe"
-
-# sh and bash <--> C:\msys64\usr\bin\bash.exe
-$null = New-Item -ItemType SymbolicLink -Path "$shellPath\bash.exe" -Target "C:\msys64\usr\bin\bash.exe"
-$null = New-Item -ItemType SymbolicLink -Path "$shellPath\sh.exe" -Target "C:\msys64\usr\bin\sh.exe"
-
-# winbash <--> C:\Windows\System32\bash.exe
-$null = New-Item -ItemType SymbolicLink -Path "$shellPath\winbash.exe" -Target "$env:SystemRoot\System32\bash.exe"
-
-# git4bash <--> C:\Program Files\Git\bin\bash.exe
-$null = New-Item -ItemType SymbolicLink -Path "$shellPath\git4bash.exe" -Target "$env:ProgramFiles\Git\bin\bash.exe"
-
-# Add shells to PATH
-Add-MachinePathItem $shellPath
\ No newline at end of file
diff --git a/images/win/scripts/Tests/Shell.Tests.ps1 b/images/win/scripts/Tests/Shell.Tests.ps1
new file mode 100644
index 00000000..e7645f2e
--- /dev/null
+++ b/images/win/scripts/Tests/Shell.Tests.ps1
@@ -0,0 +1,43 @@
+Describe "Shell" {
+    $shellTestCases = @(
+        @{Name = "C:\shells\bash.exe"; Target = "C:\msys64\usr\bin\bash.exe"},
+        @{Name = "C:\shells\sh.exe"; Target = "C:\msys64\usr\bin\sh.exe"},
+        @{Name = "C:\shells\winbash.exe"; Target = "$env:SystemRoot\System32\bash.exe"},
+        @{Name = "C:\shells\git4bash.exe"; Target = "$env:ProgramFiles\Git\bin\bash.exe"},
+        @{Name = "C:\shells\msys2.exe"; Target = "C:\msys64\usr\bin\bash.exe"}
+    )
+
+    $pathTestCases = @(
+        @{Path = "C:\shells"},
+        @{Path = "C:\msys64\mingw64\bin"},
+        @{Path = "C:\msys64\usr\bin"}
+    )
+
+    It "Default bash.exe from MSYS2" {
+        (Get-Command bash).Path | Should -BeExactly "C:\shells\bash.exe"
+    }
+
+    It "Default sh.exe from MSYS2" {
+        (Get-Command sh).Path | Should -BeExactly "C:\shells\sh.exe"
+    }
+
+    It "Folder C:\shells exists" {
+        "C:\shells" | Should -Exist
+    }
+
+    It "C:\Windows\System32 before C:\msys64\mingw64\bin and C:\msys64\usr\bin" {
+        $path = $env:Path.Split(";").ToLower()
+        $indexOfSystem32 = $path.IndexOf("c:\windows\system32")
+
+        $path.IndexOf("c:\msys64\mingw64\bin") | Should -BeGreaterThan $indexOfSystem32
+        $path.IndexOf("c:\msys64\usr\bin") | Should -BeGreaterThan $indexOfSystem32
+    }
+
+    It "<Name> target to <Target>" -TestCases $shellTestCases {
+        (Get-Item $Name).Target | Should -BeExactly $Target
+    }
+
+    It "<Path> is in PATH" -TestCases $pathTestCases {
+        $env:Path.Split(";") | Should -Contain $Path
+    }
+}
\ No newline at end of file