diff --git a/src/chocolatey/infrastructure.app/ApplicationParameters.cs b/src/chocolatey/infrastructure.app/ApplicationParameters.cs
index aaf9936d51..11fafd68a6 100644
--- a/src/chocolatey/infrastructure.app/ApplicationParameters.cs
+++ b/src/chocolatey/infrastructure.app/ApplicationParameters.cs
@@ -64,6 +64,7 @@ public static class ApplicationParameters
         public static int DefaultWaitForExitInSeconds = 2700;
 
         public static readonly string[] ConfigFileExtensions = new string[] {".autoconf",".config",".conf",".cfg",".jsc",".json",".jsonp",".ini",".xml",".yaml"};
+        public static readonly string[] ShimDirectorFileExtensions = new string[] {".gui",".ignore"};
        
         public static readonly string HashProviderFileTooBig = "UnableToDetectChanges_FileTooBig";
         public static readonly string HashProviderFileLocked = "UnableToDetectChanges_FileLocked";
diff --git a/src/chocolatey/infrastructure.app/services/NugetService.cs b/src/chocolatey/infrastructure.app/services/NugetService.cs
index 092431b58e..63da94e3ef 100644
--- a/src/chocolatey/infrastructure.app/services/NugetService.cs
+++ b/src/chocolatey/infrastructure.app/services/NugetService.cs
@@ -596,6 +596,7 @@ public ConcurrentDictionary<string, PackageResult> upgrade_run(ChocolateyConfigu
                             {
                                 rename_legacy_package_version(config, installedPackage, pkgInfo);
                                 backup_existing_version(config, installedPackage, pkgInfo);
+                                remove_shim_directors(config, installedPackage, pkgInfo);
                                 if (config.Force && (installedPackage.Version == availablePackage.Version))
                                 {
                                     FaultTolerance.try_catch_with_logging_exception(
@@ -738,6 +739,43 @@ public void backup_changed_files(string packageInstallPath, ChocolateyConfigurat
             }
         }
 
+        /// <summary>
+        /// Remove the shimgen director files from the package.
+        /// These are .gui/.ignore files that may have been created during the installation 
+        /// process and won't be pulled by the nuget package replacement.
+        /// This usually happens when package maintainers haven't been very good about how 
+        /// they create the files in the past (not using force with new-item typically throws 
+        /// an error if the file exists).
+        /// </summary>
+        /// <param name="config">The configuration.</param>
+        /// <param name="installedPackage">The installed package.</param>
+        /// <param name="pkgInfo">The package information.</param>
+        private void remove_shim_directors(ChocolateyConfiguration config, IPackage installedPackage, ChocolateyPackageInformation pkgInfo)
+        {
+            var pathResolver = NugetCommon.GetPathResolver(config, NugetCommon.GetNuGetFileSystem(config, _nugetLogger));
+            var pkgInstallPath = pathResolver.GetInstallPath(installedPackage);
+            if (!_fileSystem.directory_exists(pkgInstallPath))
+            {
+                var chocoPathResolver = pathResolver as ChocolateyPackagePathResolver;
+                if (chocoPathResolver != null)
+                {
+                    chocoPathResolver.UseSideBySidePaths = !chocoPathResolver.UseSideBySidePaths;
+                    pkgInstallPath = chocoPathResolver.GetInstallPath(installedPackage);
+                }
+            }
+
+            if (_fileSystem.directory_exists(pkgInstallPath))
+            {
+                var shimDirectorFiles = _fileSystem.get_files(pkgInstallPath, ApplicationParameters.ShimDirectorFileExtensions, SearchOption.AllDirectories);
+                foreach (var file in shimDirectorFiles.or_empty_list_if_null())
+                {
+                    FaultTolerance.try_catch_with_logging_exception(
+                        () => _fileSystem.delete_file(file),
+                        "Error deleting shim director file");
+                }
+            }
+        }
+
         public void uninstall_noop(ChocolateyConfiguration config, Action<PackageResult> continueAction)
         {
             var results = uninstall_run(config, continueAction, performAction: false);