diff --git a/packages/installer.vm/installer.vm.nuspec b/packages/installer.vm/installer.vm.nuspec
index cd1d883c8..a320e5c5c 100644
--- a/packages/installer.vm/installer.vm.nuspec
+++ b/packages/installer.vm/installer.vm.nuspec
@@ -2,7 +2,7 @@
 <package xmlns="http://schemas.microsoft.com/packaging/2015/06/nuspec.xsd">
   <metadata>
     <id>installer.vm</id>
-    <version>0.0.0.20231020</version>
+    <version>0.0.0.20231120</version>
     <authors>Mandiant</authors>
     <description>Generic installer for custom virtual machines.</description>
     <dependencies>
diff --git a/packages/installer.vm/tools/chocolateyinstall.ps1 b/packages/installer.vm/tools/chocolateyinstall.ps1
index c2017bcd5..636936d42 100644
--- a/packages/installer.vm/tools/chocolateyinstall.ps1
+++ b/packages/installer.vm/tools/chocolateyinstall.ps1
@@ -32,6 +32,23 @@ try {
     }
     VM-Write-Log "INFO" "Packages installation complete"
 
+    # Create an Admin Command Prompt shortcut to pin to taskbar
+    $toolName = 'Admin Command Prompt'
+    $category = 'Utilities'
+    $toolDir = Join-Path ${Env:TOOL_LIST_DIR}
+
+    $executablePath = Join-Path ${Env:SystemRoot} 'system32\cmd.exe'
+    $shortcutDir = Join-Path $toolDir $category -Resolve
+    $shortcut = Join-Path $shortcutDir "$toolName.lnk"
+
+    Install-ChocolateyShortcut -shortcutFilePath $shortcut -targetPath $executablePath -RunAsAdmin
+    VM-Assert-Path $shortcut
+
+    ## Configure taskbar with custom Start Layout
+    $customLayout = Join-Path ${Env:USERPROFILE} 'Desktop\CustomStartLayout.xml'
+    Import-StartLayout -LayoutPath $customLayout -MountPath "C:\"
+    Stop-Process -Name explorer -Force  # This restarts the explorer process so that the new taskbar is displayed.
+
     # Set Profile/Version specific configurations
     VM-Write-Log "INFO" "Beginning Windows OS VM profile configuration changes"
     $configPath = Join-Path $Env:VM_COMMON_DIR "config.xml" -Resolve
@@ -226,4 +243,3 @@ Thank you!
 } catch {
     VM-Write-Log-Exception $_
 }
-