diff --git a/src/NzbDrone.Core.Test/Datastore/Migration/099_extra_and_subtitle_filesFixture.cs b/src/NzbDrone.Core.Test/Datastore/Migration/099_extra_and_subtitle_filesFixture.cs
index d18f37fd1..f72d950f0 100644
--- a/src/NzbDrone.Core.Test/Datastore/Migration/099_extra_and_subtitle_filesFixture.cs
+++ b/src/NzbDrone.Core.Test/Datastore/Migration/099_extra_and_subtitle_filesFixture.cs
@@ -33,6 +33,15 @@ public void should_set_extension_using_relative_path()
                     Type = 5,
                     Consumer = "XbmcMetadata"
                 });
+
+                c.Insert.IntoTable("MetadataFiles").Row(new
+                {
+                    SeriesId = 1,
+                    RelativePath = "Series Title",
+                    LastUpdated = "2016-05-30 20:23:02.3725923",
+                    Type = 3,
+                    Consumer = "RoksboxMetadata"
+                });
             });
 
             var items = db.Query<MetadataFile99>("SELECT * FROM MetadataFiles");
diff --git a/src/NzbDrone.Core/Datastore/Migration/099_extra_and_subtitle_files.cs b/src/NzbDrone.Core/Datastore/Migration/099_extra_and_subtitle_files.cs
index 60abad5fb..f7a173157 100644
--- a/src/NzbDrone.Core/Datastore/Migration/099_extra_and_subtitle_files.cs
+++ b/src/NzbDrone.Core/Datastore/Migration/099_extra_and_subtitle_files.cs
@@ -33,6 +33,9 @@ protected override void MainDbUpgrade()
                  .AddColumn("Added").AsDateTime().Nullable()
                  .AddColumn("Extension").AsString().Nullable();
 
+            // Remove Metadata files that don't have an extension
+            Execute.Sql("DELETE FROM MetadataFiles WHERE RelativePath NOT LIKE '%.%'");
+
             // Set Extension using the extension from RelativePath
             Execute.WithConnection(SetMetadataFileExtension);
 
diff --git a/src/NzbDrone.Core/Extras/MetaData/Consumers/Roksbox/RoksboxMetadata.cs b/src/NzbDrone.Core/Extras/MetaData/Consumers/Roksbox/RoksboxMetadata.cs
index 072e3428d..de6b17a97 100644
--- a/src/NzbDrone.Core/Extras/MetaData/Consumers/Roksbox/RoksboxMetadata.cs
+++ b/src/NzbDrone.Core/Extras/MetaData/Consumers/Roksbox/RoksboxMetadata.cs
@@ -195,7 +195,7 @@ public override List<ImageFileResult> SeriesImages(Series series)
             }
 
             var source = _mediaCoverService.GetCoverPath(series.Id, image.CoverType);
-            var destination = Path.Combine(series.Path, Path.GetFileName(series.Path) + Path.GetExtension(source));
+            var destination = Path.GetFileName(series.Path) + Path.GetExtension(source);
 
             return new List<ImageFileResult>{ new ImageFileResult(destination, source) };
         }
@@ -220,7 +220,7 @@ public override List<ImageFileResult> SeasonImages(Series series, Season season)
             }
 
             var filename = Path.GetFileName(seasonFolder) + ".jpg";
-            var path = Path.Combine(series.Path, seasonFolder, filename);
+            var path = series.Path.GetRelativePath(Path.Combine(series.Path, seasonFolder, filename));
 
             return new List<ImageFileResult> { new ImageFileResult(path, image.Url) };
         }