diff --git a/assets/Product.wxs b/assets/Product.wxs
index 0f21e71becf..c07071e43d0 100644
--- a/assets/Product.wxs
+++ b/assets/Product.wxs
@@ -73,6 +73,8 @@
                   Return="ignore"
                   Impersonate="no" />
     <InstallExecuteSequence>
+      <!-- Do not remove shortcuts on upgrade to preserve user shortcuts pinned to Taskbar, see https://stackoverflow.com/a/33402698/1810304 -->
+      <RemoveShortcuts>Installed AND NOT UPGRADINGPRODUCTCODE</RemoveShortcuts>
       <Custom Action="RegisterManifest" After="InstallFiles">
         <![CDATA[NOT Installed AND (REGISTER_MANIFEST=1)]]>
       </Custom>
@@ -228,7 +230,7 @@
       </Directory>
       <Directory Id="ProgramMenuFolder">
         <Directory Id="ApplicationProgramsFolder" Name="$(var.ProductName)">
-          <Component Id="ApplicationProgramsMenuShortcut" Guid="*">
+          <Component Id="ApplicationProgramsMenuShortcut" Guid="$(env.ApplicationProgramsMenuShortcut)">
             <Shortcut Id="PowerShell_ProgramsMenuShortcut"
                       Name="$(var.ProductSimpleVersionWithNameAndOptionalArchitecture)"
                       Description="$(var.ProductSimpleVersionWithNameAndOptionalArchitecture)"
diff --git a/tools/packaging/packaging.psm1 b/tools/packaging/packaging.psm1
index 85d28dafe5f..a189ebc8be7 100644
--- a/tools/packaging/packaging.psm1
+++ b/tools/packaging/packaging.psm1
@@ -2635,6 +2635,8 @@ function New-MSIPackage
         [Environment]::SetEnvironmentVariable("UpgradeCodeX64", '31ab5147-9a97-4452-8443-d9709f0516e1', "Process")
         [Environment]::SetEnvironmentVariable("UpgradeCodeX86", '1d00683b-0f84-4db8-a64f-2f98ad42fe06', "Process")
         [Environment]::SetEnvironmentVariable("IconPath", 'assets\Powershell_black.ico', "Process")
+        # The ApplicationProgramsMenuShortcut GUID should be changed when bumping the major version because the installation directory changes
+        [Environment]::SetEnvironmentVariable("ApplicationProgramsMenuShortcut", '6a69de6c-183d-4bf4-a40e-83007d6293bf', "Process")
     }
     else
     {
@@ -2642,6 +2644,7 @@ function New-MSIPackage
         [Environment]::SetEnvironmentVariable("UpgradeCodeX64", '39243d76-adaf-42b1-94fb-16ecf83237c8', "Process")
         [Environment]::SetEnvironmentVariable("UpgradeCodeX86", '86abcfbd-1ccc-4a88-b8b2-0facfde29094', "Process")
         [Environment]::SetEnvironmentVariable("IconPath", 'assets\Powershell_av_colors.ico', "Process")
+        [Environment]::SetEnvironmentVariable("ApplicationProgramsMenuShortcut", 'ab727c4f-2311-474c-9ade-f2c6fd7f7322', "Process")
     }
     $fileArchitecture = 'amd64'
     $ProductProgFilesDir = "ProgramFiles64Folder"