diff --git a/src/chocolatey/infrastructure.app/services/NugetService.cs b/src/chocolatey/infrastructure.app/services/NugetService.cs
index 63159fd59d..b38ea3fc59 100644
--- a/src/chocolatey/infrastructure.app/services/NugetService.cs
+++ b/src/chocolatey/infrastructure.app/services/NugetService.cs
@@ -1146,6 +1146,8 @@ public virtual void backup_existing_version(ChocolateyConfiguration config, IPac
                     try
                     {
                         _fileSystem.copy_directory(backupLocation, pkgInstallPath, overwriteExisting: true);
+
+                        remove_packaging_files_prior_to_upgrade(pkgInstallPath, config.CommandName);
                     }
                     catch (Exception ex)
                     {
@@ -1167,6 +1169,29 @@ process locking the folder or files. Please make sure nothing is
             }
         }
 
+        public virtual void remove_packaging_files_prior_to_upgrade(string directoryPath, string commandName)
+        {
+            if (commandName.to_lower() == "upgrade")
+            {
+                // Due to the way that Package Reducer works, there is a potential that a Chocolatey Packaging
+                // script could be incorrectly left in place during an upgrade operation.  To guard against this,
+                // remove any Chocolatey Packaging scripts, which will then be restored by the new package, if
+                // they are still required
+                var filesToDelete = new List<string> {"chocolateyinstall", "chocolateyuninstall", "chocolateybeforemodify"};
+                var packagingScripts = _fileSystem.get_files(directoryPath, "*.ps1", SearchOption.AllDirectories)
+                    .Where(p => filesToDelete.Contains(_fileSystem.get_file_name_without_extension(p).to_lower()));
+
+                foreach (var packagingScript in packagingScripts)
+                {
+                    if (_fileSystem.file_exists(packagingScript))
+                    {
+                        this.Log().Debug("Deleting file {0}".format_with(packagingScript));
+                        _fileSystem.delete_file(packagingScript);
+                    }
+                }
+            }
+        }
+
         public virtual void backup_changed_files(string packageInstallPath, ChocolateyConfiguration config, ChocolateyPackageInformation packageInfo)
         {
             if (packageInfo == null || packageInfo.Package == null) return;