diff --git a/src/NzbDrone.Common.Test/PathExtensionFixture.cs b/src/NzbDrone.Common.Test/PathExtensionFixture.cs
index 53d27ea8c..b85fdfcdd 100644
--- a/src/NzbDrone.Common.Test/PathExtensionFixture.cs
+++ b/src/NzbDrone.Common.Test/PathExtensionFixture.cs
@@ -149,7 +149,7 @@ namespace NzbDrone.Common.Test
         }
 
         [TestCase(@"/", null)]
-        [TestCase(@"/test", null)]
+        [TestCase(@"/test", "/")]
         public void path_should_return_parent_mono(string path, string parentPath)
         {
             MonoOnly();
@@ -164,8 +164,8 @@ namespace NzbDrone.Common.Test
             // This test will fail on Windows if long path support is not enabled: https://www.howtogeek.com/266621/how-to-make-windows-10-accept-file-paths-over-260-characters/
             // It will also fail if the app isn't configured to use long path (such as resharper): https://blogs.msdn.microsoft.com/jeremykuhne/2016/07/30/net-4-6-2-and-long-paths-on-windows-10/
 
-            var path       = @"C:\media\2e168617-f2ae-43fb-b88c-3663af1c8eea\downloads\sabnzbd\nzbdrone\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories";
-            var parentPath = @"C:\media\2e168617-f2ae-43fb-b88c-3663af1c8eea\downloads\sabnzbd\nzbdrone\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing";
+            var path       = @"C:\media\2e168617-f2ae-43fb-b88c-3663af1c8eea\downloads\sabnzbd\nzbdrone\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories".AsOsAgnostic();
+            var parentPath = @"C:\media\2e168617-f2ae-43fb-b88c-3663af1c8eea\downloads\sabnzbd\nzbdrone\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing\With.Alot.Of.Nested.Directories\Some.Real.Big.Thing".AsOsAgnostic();
 
             path.GetParentPath().Should().Be(parentPath);
         }
diff --git a/src/NzbDrone.Common/Extensions/PathExtensions.cs b/src/NzbDrone.Common/Extensions/PathExtensions.cs
index 5a29bdc9c..f4c0d0d21 100644
--- a/src/NzbDrone.Common/Extensions/PathExtensions.cs
+++ b/src/NzbDrone.Common/Extensions/PathExtensions.cs
@@ -73,6 +73,11 @@ namespace NzbDrone.Common.Extensions
                 ? PARENT_PATH_END_SLASH_REGEX.Replace(childPath, "")
                 : childPath.TrimEnd(Path.DirectorySeparatorChar);
 
+            if (cleanPath.IsNullOrWhiteSpace())
+            {
+                return null;
+            }
+
             return Directory.GetParent(cleanPath)?.FullName;
         }
 
diff --git a/src/NzbDrone.Core/MediaFiles/EpisodeImport/ImportApprovedEpisodes.cs b/src/NzbDrone.Core/MediaFiles/EpisodeImport/ImportApprovedEpisodes.cs
index f44dcdf0a..7593615f6 100644
--- a/src/NzbDrone.Core/MediaFiles/EpisodeImport/ImportApprovedEpisodes.cs
+++ b/src/NzbDrone.Core/MediaFiles/EpisodeImport/ImportApprovedEpisodes.cs
@@ -183,7 +183,7 @@ namespace NzbDrone.Core.MediaFiles.EpisodeImport
                 return grandparentPath.GetRelativePath(path);
             }
 
-            return Path.Combine(Path.GetFileName(parentPath), Path.GetFileName(path));
+            return Path.GetFileName(path);
         }
 
         private string GetSceneName(DownloadClientItem downloadClientItem, LocalEpisode localEpisode)