diff --git a/ErsatzTV.Core/Scheduling/PlaylistEnumerator.cs b/ErsatzTV.Core/Scheduling/PlaylistEnumerator.cs
index 7b9845331..0b405c241 100644
--- a/ErsatzTV.Core/Scheduling/PlaylistEnumerator.cs
+++ b/ErsatzTV.Core/Scheduling/PlaylistEnumerator.cs
@@ -78,7 +78,7 @@ public class PlaylistEnumerator : IMediaCollectionEnumerator
         }
     }
 
-    public ImmutableDictionary<CollectionKey, IMediaCollectionEnumerator> ChildEnumerators { get; private set; }
+    public ImmutableList<PlaylistEnumeratorCollectionKey> ChildEnumerators { get; private set; }
 
     public int EnumeratorIndex => _enumeratorIndex;
 
@@ -213,7 +213,16 @@ public class PlaylistEnumerator : IMediaCollectionEnumerator
             }
         }
 
-        result.ChildEnumerators = enumeratorMap.ToImmutableDictionary();
+        var childEnumerators = new List<PlaylistEnumeratorCollectionKey>();
+        foreach (IMediaCollectionEnumerator enumerator in result._sortedEnumerators)
+        {
+            foreach ((CollectionKey collectionKey, _) in enumeratorMap.Find(e => e.Value == enumerator))
+            {
+                childEnumerators.Add(new PlaylistEnumeratorCollectionKey(enumerator, collectionKey));
+            }
+        }
+
+        result.ChildEnumerators = childEnumerators.ToImmutableList();
 
         return result;
     }
diff --git a/ErsatzTV.Core/Scheduling/PlaylistEnumeratorCollectionKey.cs b/ErsatzTV.Core/Scheduling/PlaylistEnumeratorCollectionKey.cs
new file mode 100644
index 000000000..aee13ed64
--- /dev/null
+++ b/ErsatzTV.Core/Scheduling/PlaylistEnumeratorCollectionKey.cs
@@ -0,0 +1,5 @@
+using ErsatzTV.Core.Interfaces.Scheduling;
+
+namespace ErsatzTV.Core.Scheduling;
+
+public record PlaylistEnumeratorCollectionKey(IMediaCollectionEnumerator Enumerator, CollectionKey CollectionKey);
diff --git a/ErsatzTV.Core/Scheduling/YamlScheduling/EnumeratorCache.cs b/ErsatzTV.Core/Scheduling/YamlScheduling/EnumeratorCache.cs
index 88dc9a66e..0c59cd3a2 100644
--- a/ErsatzTV.Core/Scheduling/YamlScheduling/EnumeratorCache.cs
+++ b/ErsatzTV.Core/Scheduling/YamlScheduling/EnumeratorCache.cs
@@ -123,6 +123,13 @@ public class EnumeratorCache(IMediaCollectionRepository mediaCollectionRepositor
             Dictionary<PlaylistItem, List<MediaItem>> itemMap =
                 await mediaCollectionRepository.GetPlaylistItemMap(playlist.PlaylistGroup, playlist.Playlist);
 
+            // foreach ((PlaylistItem playlistItem, List<MediaItem> mediaItems) in itemMap)
+            // {
+            //     _playlistMediaItems.Add(
+            //         new PlaylistKey(contentKey, CollectionKey.ForPlaylistItem(playlistItem)),
+            //         mediaItems);
+            // }
+
             return await PlaylistEnumerator.Create(
                 mediaCollectionRepository,
                 itemMap,
diff --git a/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutApplyHistoryHandler.cs b/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutApplyHistoryHandler.cs
index dae201fe2..5c2aa9f31 100644
--- a/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutApplyHistoryHandler.cs
+++ b/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutApplyHistoryHandler.cs
@@ -68,9 +68,8 @@ public class YamlPlayoutApplyHistoryHandler(EnumeratorCache enumeratorCache)
                         itemPlaybackOrder = PlaybackOrder.None;
                     }
 
-                    var childEnumeratorKeys = playlistEnumerator.ChildEnumerators.Keys.ToList();
-                    foreach ((CollectionKey collectionKey, IMediaCollectionEnumerator childEnumerator) in
-                             playlistEnumerator.ChildEnumerators)
+                    var childEnumeratorKeys = playlistEnumerator.ChildEnumerators.Map(x => x.CollectionKey).ToList();
+                    foreach ((IMediaCollectionEnumerator childEnumerator, CollectionKey collectionKey) in playlistEnumerator.ChildEnumerators)
                     {
                         Option<PlayoutHistory> maybeApplicableHistory = maybeHistory
                             .Filter(h => h.ChildKey == HistoryDetails.KeyForCollectionKey(collectionKey))
@@ -82,13 +81,17 @@ public class YamlPlayoutApplyHistoryHandler(EnumeratorCache enumeratorCache)
                         foreach (PlayoutHistory h in maybeApplicableHistory)
                         {
                             // logger.LogDebug(
-                            //     "History is applicable: {When}: {ChildKey} / {History}",
+                            //     "History is applicable: {When}: {ChildKey} / {History} / {IsCurrentChild}",
                             //     h.When,
                             //     h.ChildKey,
-                            //     h.Details);
+                            //     h.Details,
+                            //     h.IsCurrentChild);
 
-                            enumerator.ResetState(
-                                new CollectionEnumeratorState { Seed = enumerator.State.Seed, Index = h.Index + 1 });
+                            enumerator.ResetState(new CollectionEnumeratorState
+                            {
+                                Seed = enumerator.State.Seed,
+                                Index = h.Index + (h.IsCurrentChild ? 1 : 0)
+                            });
 
                             if (itemPlaybackOrder is PlaybackOrder.Chronological)
                             {
@@ -97,7 +100,7 @@ public class YamlPlayoutApplyHistoryHandler(EnumeratorCache enumeratorCache)
                                     h.Details,
                                     childEnumerator,
                                     playbackOrder,
-                                    h.IsCurrentChild);
+                                    !h.IsCurrentChild);
                             }
 
                             if (h.IsCurrentChild)
diff --git a/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutContentHandler.cs b/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutContentHandler.cs
index bca7da00b..84ad0baf1 100644
--- a/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutContentHandler.cs
+++ b/ErsatzTV.Core/Scheduling/YamlScheduling/Handlers/YamlPlayoutContentHandler.cs
@@ -91,10 +91,10 @@ public abstract class YamlPlayoutContentHandler(EnumeratorCache enumeratorCache)
 
             result.Add(nextHistory);
 
-            var childEnumeratorKeys = playlistEnumerator.ChildEnumerators.Keys.ToList();
-            foreach ((CollectionKey collectionKey, IMediaCollectionEnumerator childEnumerator) in playlistEnumerator.ChildEnumerators)
+            for (var i = 0; i < playlistEnumerator.ChildEnumerators.Count; i++)
             {
-                bool isCurrentChild = childEnumeratorKeys.IndexOf(collectionKey) == playlistEnumerator.EnumeratorIndex;
+                (IMediaCollectionEnumerator childEnumerator, CollectionKey collectionKey) = playlistEnumerator.ChildEnumerators[i];
+                bool isCurrentChild = i == playlistEnumerator.EnumeratorIndex;
                 foreach (MediaItem currentMediaItem in childEnumerator.Current)
                 {
                     // create a playout history record