diff --git a/ErsatzTV.Core/Scheduling/PlayoutModeSchedulerBase.cs b/ErsatzTV.Core/Scheduling/PlayoutModeSchedulerBase.cs
index 2221367a..fb4a01be 100644
--- a/ErsatzTV.Core/Scheduling/PlayoutModeSchedulerBase.cs
+++ b/ErsatzTV.Core/Scheduling/PlayoutModeSchedulerBase.cs
@@ -704,7 +704,7 @@ public abstract class PlayoutModeSchedulerBase<T> : IPlayoutModeScheduler<T> whe
 
         return result;
     }
-
+    
     private List<PlayoutItem> AddDurationFiller(
         PlayoutBuilderState playoutBuilderState,
         IMediaCollectionEnumerator enumerator,
@@ -715,17 +715,50 @@ public abstract class PlayoutModeSchedulerBase<T> : IPlayoutModeScheduler<T> whe
         CancellationToken cancellationToken)
     {
         var result = new List<PlayoutItem>();
+        var candidatePlayoutItems = new List<PlayoutItem>();
 
-        TimeSpan remainingToFill = duration;
-        while (enumerator.Current.IsSome && remainingToFill > TimeSpan.Zero &&
-               remainingToFill >= enumerator.MinimumDuration)
+        // First pass: Collect all possible playout items from available media
+        var processedMediaItemIds = new System.Collections.Generic.HashSet<int>();
+
+        while (enumerator.Current.IsSome)
         {
+            bool foundNewItem = false;
+
             foreach (MediaItem mediaItem in enumerator.Current)
             {
+                // Skip if we've already processed this media item
+                if (processedMediaItemIds.Contains(mediaItem.Id))
+                    continue;
+
+                processedMediaItemIds.Add(mediaItem.Id);
+                foundNewItem = true;
+
                 TimeSpan itemDuration = DurationForMediaItem(mediaItem);
+                List<MediaChapter> itemChapters = ChaptersForMediaItem(mediaItem);
 
-                if (remainingToFill - itemDuration >= TimeSpan.Zero)
+                if (itemChapters.Count > 1)
+                {
+                    // Add each chapter as a separate candidate
+                    foreach (MediaChapter chapter in itemChapters)
+                    {
+                        TimeSpan chapterDuration = chapter.EndTime - chapter.StartTime;
+                        var playoutItem = new PlayoutItem
+                        {
+                            MediaItemId = mediaItem.Id,
+                            Start = new DateTime(2020, 2, 1, 0, 0, 0, DateTimeKind.Utc),
+                            Finish = new DateTime(2020, 2, 1, 0, 0, 0, DateTimeKind.Utc) + chapterDuration,
+                            InPoint = chapter.StartTime,
+                            OutPoint = chapter.EndTime,
+                            GuideGroup = playoutBuilderState.NextGuideGroup,
+                            FillerKind = fillerKind,
+                            DisableWatermarks = !allowWatermarks
+                        };
+                        candidatePlayoutItems.Add(playoutItem);
+                    }
+                }
+                else
                 {
+                    // Add the full media item as a candidate
                     var playoutItem = new PlayoutItem
                     {
                         MediaItemId = mediaItem.Id,
@@ -737,22 +770,43 @@ public abstract class PlayoutModeSchedulerBase<T> : IPlayoutModeScheduler<T> whe
                         FillerKind = fillerKind,
                         DisableWatermarks = !allowWatermarks
                     };
-
-                    remainingToFill -= itemDuration;
-                    result.Add(playoutItem);
-                    enumerator.MoveNext();
+                    candidatePlayoutItems.Add(playoutItem);
                 }
-                else
-                {
-                    if (log)
-                    {
-                        Logger.LogDebug(
-                            "Filler item is too long {FillerDuration:g} to fill {GapDuration:g}; skipping to next filler item",
-                            itemDuration,
-                            remainingToFill);
-                    }
+            }
+
+            // If we didn't find any new items, we've seen all items - break the loop
+            if (!foundNewItem)
+                break;
+
+            enumerator.MoveNext();
+        }
+
+        // Shuffle all candidate playout items
+        var random = new Random();
+        candidatePlayoutItems = candidatePlayoutItems.OrderBy(x => random.Next()).ToList();
+
+        // Second pass: Add shuffled items until duration is filled
+        TimeSpan remainingToFill = duration;
+        foreach (var playoutItem in candidatePlayoutItems)
+        {
+            if (remainingToFill <= TimeSpan.Zero)
+                break;
 
-                    enumerator.MoveNext();
+            TimeSpan itemDuration = playoutItem.Finish - playoutItem.Start;
+
+            if (remainingToFill >= itemDuration)
+            {
+                remainingToFill -= itemDuration;
+                result.Add(playoutItem);
+            }
+            else
+            {
+                if (log)
+                {
+                    Logger.LogDebug(
+                        "Filler item is too long {FillerDuration:g} to fill {GapDuration:g}; skipping to next filler item",
+                        itemDuration,
+                        remainingToFill);
                 }
             }
         }