diff --git a/nuget/chocolatey/tools/chocolateysetup.psm1 b/nuget/chocolatey/tools/chocolateysetup.psm1
index 581671bb59..cc68f23f82 100644
--- a/nuget/chocolatey/tools/chocolateysetup.psm1
+++ b/nuget/chocolatey/tools/chocolateysetup.psm1
@@ -30,13 +30,56 @@ param (
   }
 }
 
+function Remove-ShimWithAuthenticodeSignature {
+  param (
+    [string] $filePath
+  )
+  if (!(Test-Path $filePath)) {
+    return
+  }
+
+  $signature = Get-AuthenticodeSignature $filePath -ErrorAction SilentlyContinue
+
+  if (!$signature -or !$signature.SignerCertificate) {
+    Write-ChocolateyWarning "Shim found in $filePath, but was not signed. Ignoring removal..."
+    return
+  }
+
+  $possibleSignatures = @(
+    'RealDimensions Software, LLC'
+    'Chocolatey Software, Inc\.'
+  )
+
+  $possibleSignatures | ForEach-Object {
+    if ($signature.SignerCertificate.Subject -match "$_") {
+      Write-Output "Removing shim $filePath"
+      $null = Remove-Item "$filePath"
+
+      if (Test-Path "$filePath.ignore") {
+        $null = Remove-Item "$filePath.ignore"
+      }
+
+      if (Test-Path "$filePath.old") {
+        $null = Remove-Item "$filePath.old"
+      }
+    }
+  }
+
+  # This means the file was found, however did not get removed as it contained a authenticode signature that
+  # is not ours.
+  if (Test-Path $filePath) {
+    Write-ChocolateyWarning "Shim found in $filePath, but did not match our signature. Ignoring removal..."
+    return
+  }
+}
+
 function Initialize-Chocolatey {
 <#
   .DESCRIPTION
     This will initialize the Chocolatey tool by
       a) setting up the "chocolateyPath" (the location where all chocolatey nuget packages will be installed)
       b) Installs chocolatey into the "chocolateyPath"
-            c) Instals .net 4.0 if needed
+            c) Installs .net 4.0 if needed
       d) Adds Chocolatey to the PATH environment variable so you have access to the choco commands.
   .PARAMETER  ChocolateyPath
     Allows you to override the default path of (C:\ProgramData\chocolatey\) by specifying a directory chocolatey will install nuget packages.
@@ -142,6 +185,28 @@ You may need to shut down and restart powershell and/or consoles
   if (-not $allowInsecureRootInstall) {
     Remove-OldChocolateyInstall $defaultChocolateyPathOld
   }
+
+  $possiblePaths = @(
+    $chocolateyExePath
+    Join-Path "$chocolateyPath" "redirects"
+    Join-Path "$thisScriptFolder" "chocolateyInstall\redirects"
+  )
+
+  $shimsToRemove = @("cpack.exe")
+  $possiblePaths | ForEach-Object {
+    $path = $_
+    $shimsToRemove | ForEach-Object { Join-Path $path $_ } | Where-Object { Test-Path $_ } | ForEach-Object {
+      $path = $_
+      Write-Debug "Removing shim from '$path'."
+
+      try {
+        Remove-ShimWithAuthenticodeSignature -filePath $path
+      }
+      catch {
+        Write-ChocolateyWarning "Unable to remove '$path'. Please remove the file manually."
+      }
+    }
+  }
 }
 
 function Set-ChocolateyInstallFolder {