diff --git a/CHANGELOG.md b/CHANGELOG.md
index 721921807..b326eb59c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -15,6 +15,9 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/).
 - Fix song normalization to match FFmpeg Profile bit depth
 - Fix bug playing some external subtitle files (e.g. with an apostrophe in the file name)
 - Fix bug detecting VAAPI capabilities when no device is selected in active FFmpeg Profile
+- Fix playout mode duration bugs in XMLTV
+  - Tail mode filler will properly include filler duration in XMLTV
+  - Duration that wraps across midnight will no longer have overlapping items in XMLTV
 
 ### Changed
 - Ignore case of video and audio file extensions in local folder scanner
diff --git a/ErsatzTV.Core.Tests/Scheduling/PlayoutModeSchedulerDurationTests.cs b/ErsatzTV.Core.Tests/Scheduling/PlayoutModeSchedulerDurationTests.cs
index eb25b482f..6f06113cb 100644
--- a/ErsatzTV.Core.Tests/Scheduling/PlayoutModeSchedulerDurationTests.cs
+++ b/ErsatzTV.Core.Tests/Scheduling/PlayoutModeSchedulerDurationTests.cs
@@ -289,7 +289,9 @@ public class PlayoutModeSchedulerDurationTests : SchedulerTestBase
         playoutItems[2].StartOffset.Should().Be(startState.CurrentTime.Add(new TimeSpan(1, 50, 0)));
         playoutItems[2].GuideGroup.Should().Be(3);
         playoutItems[2].FillerKind.Should().Be(FillerKind.None);
-        playoutItems[2].GuideFinish.HasValue.Should().BeTrue();
+        
+        // offline should not set guide finish
+        playoutItems[2].GuideFinish.HasValue.Should().BeFalse();
     }
 
     [Test]
diff --git a/ErsatzTV.Core/Iptv/ChannelGuide.cs b/ErsatzTV.Core/Iptv/ChannelGuide.cs
index 4bad446e5..30c00cbea 100644
--- a/ErsatzTV.Core/Iptv/ChannelGuide.cs
+++ b/ErsatzTV.Core/Iptv/ChannelGuide.cs
@@ -111,7 +111,8 @@ public class ChannelGuide
 
                 int finishIndex = j;
                 while (finishIndex + 1 < sorted.Count && (sorted[finishIndex + 1].GuideGroup == startItem.GuideGroup
-                       || sorted[finishIndex + 1].FillerKind == FillerKind.GuideMode))
+                                                          || sorted[finishIndex + 1].FillerKind is FillerKind.GuideMode
+                                                              or FillerKind.Tail or FillerKind.Fallback))
                 {
                     finishIndex++;
                 }
diff --git a/ErsatzTV.Core/Scheduling/PlayoutModeSchedulerDuration.cs b/ErsatzTV.Core/Scheduling/PlayoutModeSchedulerDuration.cs
index 928d5639d..240c378c4 100644
--- a/ErsatzTV.Core/Scheduling/PlayoutModeSchedulerDuration.cs
+++ b/ErsatzTV.Core/Scheduling/PlayoutModeSchedulerDuration.cs
@@ -48,10 +48,10 @@ public class PlayoutModeSchedulerDuration : PlayoutModeSchedulerBase<ProgramSche
                 {
                     DurationFinish = itemStartTime + scheduleItem.PlayoutDuration
                 };
-
-                durationUntil = nextState.DurationFinish;
             }
 
+            durationUntil = nextState.DurationFinish;
+
             TimeSpan itemDuration = DurationForMediaItem(mediaItem);
             List<MediaChapter> itemChapters = ChaptersForMediaItem(mediaItem);
 
@@ -194,10 +194,21 @@ public class PlayoutModeSchedulerDuration : PlayoutModeSchedulerBase<ProgramSche
             }
         }
 
-        // clear guide finish on all but the last item
-        var all = playoutItems.Filter(pi => pi.FillerKind == FillerKind.None).ToList();
-        PlayoutItem last = all.MaxBy(pi => pi.FinishOffset);
-        foreach (PlayoutItem item in all.Filter(pi => pi != last))
+        bool hasFallback = playoutItems.Any(p => p.FillerKind == FillerKind.Fallback);
+        
+        var playoutItemsToClear = playoutItems
+            .Filter(pi => pi.FillerKind == FillerKind.None)
+            .ToList();
+
+        PlayoutItem lastItem = playoutItemsToClear.MaxBy(pi => pi.FinishOffset);
+
+        // if we've finished the duration or are in offline tail mode with no fallback, keep guide finish on the last item 
+        if (nextState.DurationFinish.IsNone && (scheduleItem.TailMode != TailMode.Offline || hasFallback))
+        {
+            playoutItemsToClear.Remove(lastItem);
+        }
+        
+        foreach (PlayoutItem item in playoutItemsToClear)
         {
             item.GuideFinish = null;
         }