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 43396618d..d18f37fd1 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
@@ -22,12 +22,24 @@ namespace NzbDrone.Core.Test.Datastore.Migration
                     Type = 3,
                     Consumer = "XbmcMetadata"
                 });
+
+                c.Insert.IntoTable("MetadataFiles").Row(new
+                {
+                    SeriesId = 1,
+                    SeasonNumber = 1,
+                    EpisodeFileId = 1,
+                    RelativePath = "Series.Title.S01E01.jpg",
+                    LastUpdated = "2016-05-30 20:23:02.3725923",
+                    Type = 5,
+                    Consumer = "XbmcMetadata"
+                });
             });
 
             var items = db.Query<MetadataFile99>("SELECT * FROM MetadataFiles");
 
-            items.Should().HaveCount(1);
+            items.Should().HaveCount(2);
             items.First().Extension.Should().Be(".jpg");
+            items.Last().Extension.Should().Be(".jpg");
         }
     }
 }
diff --git a/src/NzbDrone.Core.Test/Datastore/Migration/103_fix_metadata_file_extensionsFixture.cs b/src/NzbDrone.Core.Test/Datastore/Migration/103_fix_metadata_file_extensionsFixture.cs
new file mode 100644
index 000000000..86905df18
--- /dev/null
+++ b/src/NzbDrone.Core.Test/Datastore/Migration/103_fix_metadata_file_extensionsFixture.cs
@@ -0,0 +1,36 @@
+using System.Linq;
+using FluentAssertions;
+using NUnit.Framework;
+using NzbDrone.Core.Datastore.Migration;
+using NzbDrone.Core.Test.Framework;
+
+namespace NzbDrone.Core.Test.Datastore.Migration
+{
+    [TestFixture]
+    public class fix_metadata_file_extensionsFixture : MigrationTest<fix_metadata_file_extensions>
+    {
+        [Test]
+        public void should_fix_extension_when_relative_path_contained_multiple_periods()
+        {
+            var db = WithMigrationTestDb(c =>
+            {
+                c.Insert.IntoTable("MetadataFiles").Row(new
+                {
+                    SeriesId = 1,
+                    SeasonNumber = 1,
+                    EpisodeFileId = 1,
+                    RelativePath = "Series.Title.S01E01.jpg",
+                    LastUpdated = "2016-05-30 20:23:02.3725923",
+                    Type = 5,
+                    Consumer = "XbmcMetadata",
+                    Extension = ".S01E01.jpg"
+                });
+            });
+
+            var items = db.Query<MetadataFile99>("SELECT * FROM MetadataFiles");
+
+            items.Should().HaveCount(1);
+            items.First().Extension.Should().Be(".jpg");
+        }
+    }
+}
diff --git a/src/NzbDrone.Core.Test/NzbDrone.Core.Test.csproj b/src/NzbDrone.Core.Test/NzbDrone.Core.Test.csproj
index 4c8e12548..41faf14cc 100644
--- a/src/NzbDrone.Core.Test/NzbDrone.Core.Test.csproj
+++ b/src/NzbDrone.Core.Test/NzbDrone.Core.Test.csproj
@@ -119,6 +119,7 @@
     <Compile Include="Datastore\DatabaseRelationshipFixture.cs" />
     <Compile Include="Datastore\MappingExtentionFixture.cs" />
     <Compile Include="Datastore\MarrDataLazyLoadingFixture.cs" />
+    <Compile Include="Datastore\Migration\103_fix_metadata_file_extensionsFixture.cs" />
     <Compile Include="Datastore\Migration\099_extra_and_subtitle_filesFixture.cs" />
     <Compile Include="Datastore\Migration\101_add_ultrahd_quality_in_profilesFixture.cs" />
     <Compile Include="Datastore\Migration\071_unknown_quality_in_profileFixture.cs" />
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 2d7f54143..60abad5fb 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
@@ -1,4 +1,5 @@
 using System;
+using System.Data;
 using FluentMigrator;
 using NzbDrone.Core.Datastore.Migration.Framework;
 
@@ -33,10 +34,39 @@ namespace NzbDrone.Core.Datastore.Migration
                  .AddColumn("Extension").AsString().Nullable();
 
             // Set Extension using the extension from RelativePath
-            Execute.Sql("UPDATE MetadataFiles SET Extension = substr(RelativePath, instr(RelativePath, '.'));");
+            Execute.WithConnection(SetMetadataFileExtension);
 
             Alter.Table("MetadataFiles").AlterColumn("Extension").AsString().NotNullable();
         }
+
+        private void SetMetadataFileExtension(IDbConnection conn, IDbTransaction tran)
+        {
+            using (var cmd = conn.CreateCommand())
+            {
+                cmd.Transaction = tran;
+                cmd.CommandText = "SELECT Id, RelativePath FROM MetadataFiles";
+
+                using (var reader = cmd.ExecuteReader())
+                {
+                    while (reader.Read())
+                    {
+                        var id = reader.GetInt32(0);
+                        var relativePath = reader.GetString(1);
+                        var extension = relativePath.Substring(relativePath.LastIndexOf(".", StringComparison.InvariantCultureIgnoreCase));
+
+                        using (var updateCmd = conn.CreateCommand())
+                        {
+                            updateCmd.Transaction = tran;
+                            updateCmd.CommandText = "UPDATE MetadataFiles SET Extension = ? WHERE Id = ?";
+                            updateCmd.AddParameter(extension);
+                            updateCmd.AddParameter(id);
+
+                            updateCmd.ExecuteNonQuery();
+                        }
+                    }
+                }
+            }
+        }
     }
 
     public class MetadataFile99
diff --git a/src/NzbDrone.Core/Datastore/Migration/103_fix_metadata_file_extensions.cs b/src/NzbDrone.Core/Datastore/Migration/103_fix_metadata_file_extensions.cs
new file mode 100644
index 000000000..d4ed853a3
--- /dev/null
+++ b/src/NzbDrone.Core/Datastore/Migration/103_fix_metadata_file_extensions.cs
@@ -0,0 +1,45 @@
+using System;
+using System.Data;
+using FluentMigrator;
+using NzbDrone.Core.Datastore.Migration.Framework;
+
+namespace NzbDrone.Core.Datastore.Migration
+{
+    [Migration(103)]
+    public class fix_metadata_file_extensions : NzbDroneMigrationBase
+    {
+        protected override void MainDbUpgrade()
+        {
+            Execute.WithConnection(SetMetadataFileExtension);
+        }
+
+        private void SetMetadataFileExtension(IDbConnection conn, IDbTransaction tran)
+        {
+            using (var cmd = conn.CreateCommand())
+            {
+                cmd.Transaction = tran;
+                cmd.CommandText = "SELECT Id, Extension FROM MetadataFiles";
+
+                using (var reader = cmd.ExecuteReader())
+                {
+                    while (reader.Read())
+                    {
+                        var id = reader.GetInt32(0);
+                        var extension = reader.GetString(1);
+                        extension = extension.Substring(extension.LastIndexOf(".", StringComparison.InvariantCultureIgnoreCase));
+
+                        using (var updateCmd = conn.CreateCommand())
+                        {
+                            updateCmd.Transaction = tran;
+                            updateCmd.CommandText = "UPDATE MetadataFiles SET Extension = ? WHERE Id = ?";
+                            updateCmd.AddParameter(extension);
+                            updateCmd.AddParameter(id);
+
+                            updateCmd.ExecuteNonQuery();
+                        }
+                    }
+                }
+            }
+        }
+    }
+}
diff --git a/src/NzbDrone.Core/NzbDrone.Core.csproj b/src/NzbDrone.Core/NzbDrone.Core.csproj
index 6605dd5a5..3aff31e8e 100644
--- a/src/NzbDrone.Core/NzbDrone.Core.csproj
+++ b/src/NzbDrone.Core/NzbDrone.Core.csproj
@@ -251,6 +251,7 @@
     <Compile Include="Datastore\Migration\070_delay_profile.cs" />
     <Compile Include="Datastore\Migration\096_disable_kickass.cs" />
     <Compile Include="Datastore\Migration\095_add_additional_episodes_index.cs" />
+    <Compile Include="Datastore\Migration\103_fix_metadata_file_extensions.cs" />
     <Compile Include="Datastore\Migration\101_add_ultrahd_quality_in_profiles.cs" />
     <Compile Include="Datastore\Migration\071_unknown_quality_in_profile.cs" />
     <Compile Include="Datastore\Migration\072_history_grabid.cs" />