diff --git a/CHANGELOG.md b/CHANGELOG.md
index b136f0dd8..e48791313 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -91,6 +91,7 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/).
   - When this happens, mid-roll will be treated as post-roll
 - Fix VAAPI decoder capability check
   - This caused some streams to incorrectly use software decoding
+- Fix scheduling loop/failure caused by some duration schedule items
 
 ### Changed
 - Use ffmpeg 7 in all docker images
diff --git a/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs b/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs
index 5dd0eacf4..9e8ba9c6c 100644
--- a/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs
+++ b/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs
@@ -425,6 +425,8 @@ public class PlayoutBuilder : IPlayoutBuilder
             playout.ProgramScheduleAlternates,
             playoutStart);
 
+        // _logger.LogDebug("Active schedule is: {Schedule}", activeSchedule.Name);
+
         // random start points are disabled in some scenarios, so ensure it's enabled and active
         randomStartPoint = randomStartPoint && activeSchedule.RandomStartPoint;
 
@@ -562,6 +564,16 @@ public class PlayoutBuilder : IPlayoutBuilder
 
         // find start anchor
         PlayoutAnchor startAnchor = FindStartAnchor(playout, playoutStart, scheduleItemsEnumerator);
+
+        // clear duration finish if it has already passed
+        foreach (DateTimeOffset durationFinish in startAnchor.DurationFinishOffset)
+        {
+            if (durationFinish < startAnchor.NextStartOffset)
+            {
+                startAnchor.DurationFinish = null;
+            }
+        }
+
         // _logger.LogDebug("Start anchor: {@StartAnchor}", startAnchor);
 
         // start at the previously-decided time
@@ -723,7 +735,11 @@ public class PlayoutBuilder : IPlayoutBuilder
 
         foreach (DateTimeOffset durationFinish in playoutBuilderState.DurationFinish)
         {
-            playout.Anchor.DurationFinish = durationFinish.UtcDateTime;
+            // don't save duration finish if it already passed
+            if (durationFinish > playout.Anchor.NextStartOffset)
+            {
+                playout.Anchor.DurationFinish = durationFinish.UtcDateTime;
+            }
         }
 
         // build program schedule anchors
diff --git a/ErsatzTV.Core/Scheduling/PlayoutModeSchedulerDuration.cs b/ErsatzTV.Core/Scheduling/PlayoutModeSchedulerDuration.cs
index cbb65fd6f..33a3a7185 100644
--- a/ErsatzTV.Core/Scheduling/PlayoutModeSchedulerDuration.cs
+++ b/ErsatzTV.Core/Scheduling/PlayoutModeSchedulerDuration.cs
@@ -21,7 +21,8 @@ public class PlayoutModeSchedulerDuration : PlayoutModeSchedulerBase<ProgramSche
         CancellationToken cancellationToken)
     {
         // Logger.LogDebug(
-        //     "DurationSchedule: {CurrentTime} {DurationFinish} {InDurationFiller} {HardStop}",
+        //     "DurationSchedule: {ItemId} {CurrentTime} {DurationFinish} {InDurationFiller} {HardStop}",
+        //     scheduleItem.Id,
         //     playoutBuilderState.CurrentTime,
         //     playoutBuilderState.DurationFinish,
         //     playoutBuilderState.InDurationFiller,