diff --git a/src/NzbDrone.Common.Test/PathExtensionFixture.cs b/src/NzbDrone.Common.Test/PathExtensionFixture.cs
index febd93a7d..db140d626 100644
--- a/src/NzbDrone.Common.Test/PathExtensionFixture.cs
+++ b/src/NzbDrone.Common.Test/PathExtensionFixture.cs
@@ -140,6 +140,8 @@ namespace NzbDrone.Common.Test
         [TestCase(@"C:\Test\mydir", @"C:\Test")]
         [TestCase(@"C:\Test\", @"C:")]
         [TestCase(@"C:\", null)]
+        [TestCase(@"/", null)]
+        [TestCase(@"/test", null)]
         public void path_should_return_parent(string path, string parentPath)
         {
             path.GetParentPath().Should().Be(parentPath);
diff --git a/src/NzbDrone.Common/Extensions/PathExtensions.cs b/src/NzbDrone.Common/Extensions/PathExtensions.cs
index da7dd1d46..ff95d8973 100644
--- a/src/NzbDrone.Common/Extensions/PathExtensions.cs
+++ b/src/NzbDrone.Common/Extensions/PathExtensions.cs
@@ -71,10 +71,11 @@ namespace NzbDrone.Common.Extensions
 
             var index = parentPath.LastIndexOfAny(new[] { '\\', '/' });
 
-            if (index != -1)
+            if (index > 0)
             {
                 return parentPath.Substring(0, index);
             }
+
             return null;
         }
 
diff --git a/src/NzbDrone.Core.Test/MediaFiles/ImportApprovedEpisodesFixture.cs b/src/NzbDrone.Core.Test/MediaFiles/ImportApprovedEpisodesFixture.cs
index a5f50c916..f16be5c30 100644
--- a/src/NzbDrone.Core.Test/MediaFiles/ImportApprovedEpisodesFixture.cs
+++ b/src/NzbDrone.Core.Test/MediaFiles/ImportApprovedEpisodesFixture.cs
@@ -341,6 +341,23 @@ namespace NzbDrone.Core.Test.MediaFiles
 
             Mocker.GetMock<IMediaFileService>().Verify(v => v.Add(It.Is<EpisodeFile>(c => c.OriginalFilePath == $"{name}\\subfolder\\{name}.mkv".AsOsAgnostic())));
         }
+
+        [Test]
+        public void should_get_relative_path_when_there_is_no_grandparent()
+        {
+            var name = "Series.Title.S01E01.720p.HDTV.x264-Sonarr";
+            var outputPath = Path.Combine(@"C:\".AsOsAgnostic());
+            var localEpisode = _approvedDecisions.First().LocalEpisode;
+
+            localEpisode.FolderEpisodeInfo = new ParsedEpisodeInfo { ReleaseTitle = name };
+            localEpisode.Path = Path.Combine(outputPath, name + ".mkv");
+
+            Subject.Import(new List<ImportDecision> { _approvedDecisions.First() }, true, null);
+
+            Mocker.GetMock<IMediaFileService>().Verify(v => v.Add(It.Is<EpisodeFile>(c => c.OriginalFilePath == $"{name}.mkv".AsOsAgnostic())));
+        }
+
+        [Test]
         public void should_delete_existing_metadata_files_with_the_same_path()
         {
             Mocker.GetMock<IMediaFileService>()