diff --git a/src/NzbDrone.Core.Test/TvTests/EpisodeServiceTests/HandleEpisodeFileDeletedFixture.cs b/src/NzbDrone.Core.Test/TvTests/EpisodeServiceTests/HandleEpisodeFileDeletedFixture.cs
index 723917287..6f90c9716 100644
--- a/src/NzbDrone.Core.Test/TvTests/EpisodeServiceTests/HandleEpisodeFileDeletedFixture.cs
+++ b/src/NzbDrone.Core.Test/TvTests/EpisodeServiceTests/HandleEpisodeFileDeletedFixture.cs
@@ -119,5 +119,20 @@ namespace NzbDrone.Core.Test.TvTests.EpisodeServiceTests
             Mocker.GetMock<IEpisodeRepository>()
                 .Verify(v => v.ClearFileId(It.IsAny<Episode>(), false), Times.Once());
         }
+
+        [Test]
+        public void should_leave_monitored_to_true_if_autoUnmonitor_is_true_and_is_for_manual_override()
+        {
+            GivenSingleEpisodeFile();
+
+            Mocker.GetMock<IConfigService>()
+                  .SetupGet(s => s.AutoUnmonitorPreviouslyDownloadedEpisodes)
+                  .Returns(true);
+
+            Subject.Handle(new EpisodeFileDeletedEvent(_episodeFile, DeleteMediaFileReason.ManualOverride));
+
+            Mocker.GetMock<IEpisodeRepository>()
+                  .Verify(v => v.ClearFileId(It.IsAny<Episode>(), false), Times.Once());
+        }
     }
 }
diff --git a/src/NzbDrone.Core/Tv/EpisodeService.cs b/src/NzbDrone.Core/Tv/EpisodeService.cs
index 226c7b3f6..8c0b7e5be 100644
--- a/src/NzbDrone.Core/Tv/EpisodeService.cs
+++ b/src/NzbDrone.Core/Tv/EpisodeService.cs
@@ -221,7 +221,7 @@ namespace NzbDrone.Core.Tv
             {
                 _logger.Debug("Detaching episode {0} from file.", episode.Id);
 
-                var unmonitorForReason = message.Reason != DeleteMediaFileReason.Upgrade ||
+                var unmonitorForReason = message.Reason != DeleteMediaFileReason.Upgrade &&
                                          message.Reason != DeleteMediaFileReason.ManualOverride;