diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8deb5cd8f..931d23b02 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -41,6 +41,7 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/).
   - Respect `z_index` (draw order) on all graphics element types
   - Fix bug with `z_index` sorting
 - Restore default UI font that was erroneously removed in v26.1.1
+- Classic schedules: fix building playouts when `Fill With Group Mode` schedule items also have graphics elements
 - Use configured searching log level on startup, instead of the default log level of `Information`
 - MySql: fix searching for shows and seasons in schedule items editor
 - Fix 500 errors when serving XMLTV due to concurrent file reads and writes
diff --git a/ErsatzTV.Core.Tests/Fakes/FakeMediaCollectionRepository.cs b/ErsatzTV.Core.Tests/Fakes/FakeMediaCollectionRepository.cs
index 509937dfe..db87f508c 100644
--- a/ErsatzTV.Core.Tests/Fakes/FakeMediaCollectionRepository.cs
+++ b/ErsatzTV.Core.Tests/Fakes/FakeMediaCollectionRepository.cs
@@ -76,6 +76,8 @@ public class FakeMediaCollectionRepository : IMediaCollectionRepository
     public Task<bool> IsCustomPlaybackOrder(int collectionId) => false.AsTask();
     public Task<Option<string>> GetNameFromKey(CollectionKey emptyCollection, CancellationToken cancellationToken) => Option<string>.None.AsTask();
 
-    public List<CollectionWithItems> GroupIntoFakeCollections(List<MediaItem> items, string fakeKey = null) =>
-        throw new NotSupportedException();
+    public List<CollectionWithItems> GroupIntoFakeCollections(List<MediaItem> items, string fakeKey = null)
+    {
+        return [new CollectionWithItems(1, 0, fakeKey, items, true, PlaybackOrder.Shuffle, false)];
+    }
 }
diff --git a/ErsatzTV.Core.Tests/Scheduling/ClassicScheduling/NewPlayoutTests.cs b/ErsatzTV.Core.Tests/Scheduling/ClassicScheduling/NewPlayoutTests.cs
index e1da25e24..bf3a4d225 100644
--- a/ErsatzTV.Core.Tests/Scheduling/ClassicScheduling/NewPlayoutTests.cs
+++ b/ErsatzTV.Core.Tests/Scheduling/ClassicScheduling/NewPlayoutTests.cs
@@ -15,6 +15,103 @@ namespace ErsatzTV.Core.Tests.Scheduling.ClassicScheduling;
 [TestFixture]
 public class NewPlayoutTests : PlayoutBuilderTestBase
 {
+    [Test]
+    public async Task FillWithGroupMode_Should_Not_Fail()
+    {
+        var collection = new Collection
+        {
+            Id = 1,
+            Name = "Multiple Items",
+            MediaItems =
+            [
+                TestMovie(1, TimeSpan.FromHours(1), new DateTime(2020, 1, 1)),
+                TestMovie(2, TimeSpan.FromHours(1), new DateTime(2020, 2, 1))
+            ]
+        };
+
+        var fakeRepository = new FakeMediaCollectionRepository(
+            Map((collection.Id, collection.MediaItems.ToList())));
+
+        var items = new List<ProgramScheduleItem>
+        {
+            new ProgramScheduleItemMultiple
+            {
+                Id = 1,
+                Index = 1,
+                //Collection = collection,
+                CollectionId = collection.Id,
+                StartTime = null,
+                PlaybackOrder = PlaybackOrder.Chronological,
+                MultipleMode = MultipleMode.Count,
+                Count = "2",
+                FillWithGroupMode = FillWithGroupMode.FillWithShuffledGroups,
+                ProgramScheduleItemGraphicsElements = []
+            }
+        };
+
+        // having a graphics element reference the schedule item triggers the bug
+        items[0].ProgramScheduleItemGraphicsElements.Add(new ProgramScheduleItemGraphicsElement
+        {
+            GraphicsElementId = 1,
+            ProgramScheduleItem = items[0],
+            ProgramScheduleItemId = items[0].Id
+        });
+
+        var playout = new Playout
+        {
+            ProgramSchedule = new ProgramSchedule
+            {
+                Items = items
+            },
+            Channel = new Channel(Guid.Empty) { Id = 1, Name = "Test Channel" },
+            ProgramScheduleAnchors = [],
+            Items = [],
+            ProgramScheduleAlternates = [],
+            FillGroupIndices = []
+        };
+
+        var referenceData =
+            new PlayoutReferenceData(
+                playout.Channel,
+                Option<Deco>.None,
+                [],
+                [],
+                playout.ProgramSchedule,
+                [],
+                [],
+                TimeSpan.Zero);
+
+        IConfigElementRepository configRepo = Substitute.For<IConfigElementRepository>();
+        var televisionRepo = new FakeTelevisionRepository();
+        IArtistRepository artistRepo = Substitute.For<IArtistRepository>();
+        IMultiEpisodeShuffleCollectionEnumeratorFactory factory =
+            Substitute.For<IMultiEpisodeShuffleCollectionEnumeratorFactory>();
+        IRerunHelper rerunHelper = Substitute.For<IRerunHelper>();
+        var builder = new PlayoutBuilder(
+            configRepo,
+            fakeRepository,
+            televisionRepo,
+            artistRepo,
+            factory,
+            new MockFileSystem(),
+            rerunHelper,
+            Logger);
+
+        DateTimeOffset start = HoursAfterMidnight(0);
+        DateTimeOffset finish = start + TimeSpan.FromHours(6);
+
+        Either<BaseError, PlayoutBuildResult> buildResult = await builder.Build(
+            playout,
+            referenceData,
+            PlayoutBuildResult.Empty,
+            PlayoutBuildMode.Reset,
+            start,
+            finish,
+            CancellationToken);
+
+        buildResult.IsRight.ShouldBeTrue();
+    }
+
     [Test]
     public async Task OnlyZeroDurationItem_Should_Abort()
     {
diff --git a/ErsatzTV.Core/Extensions/ProgramScheduleItemExtensions.cs b/ErsatzTV.Core/Extensions/ProgramScheduleItemExtensions.cs
new file mode 100644
index 000000000..53f2ffc06
--- /dev/null
+++ b/ErsatzTV.Core/Extensions/ProgramScheduleItemExtensions.cs
@@ -0,0 +1,25 @@
+using ErsatzTV.Core.Domain;
+using Newtonsoft.Json;
+
+namespace ErsatzTV.Core.Extensions;
+
+public static class ProgramScheduleItemExtensions
+{
+    public static ProgramScheduleItem DeepCopy(this ProgramScheduleItem item)
+    {
+        if (item == null)
+        {
+            return null;
+        }
+
+        var settings = new JsonSerializerSettings
+        {
+            // program schedule item => graphics element => (same) program schedule item should be ignored
+            ReferenceLoopHandling = ReferenceLoopHandling.Ignore,
+            NullValueHandling = NullValueHandling.Ignore
+        };
+
+        string json = JsonConvert.SerializeObject(item, settings);
+        return (ProgramScheduleItem)JsonConvert.DeserializeObject(json, item.GetType(), settings);
+    }
+}
diff --git a/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs b/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs
index 16add392d..1d467f567 100644
--- a/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs
+++ b/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs
@@ -1,5 +1,4 @@
 using System.IO.Abstractions;
-using System.Reflection;
 using ErsatzTV.Core.Domain;
 using ErsatzTV.Core.Domain.Filler;
 using ErsatzTV.Core.Errors;
@@ -673,13 +672,6 @@ public class PlayoutBuilder : IPlayoutBuilder
                 .Filter(c => c.ShowId > 0 || c.ArtistId > 0 || !string.IsNullOrWhiteSpace(c.Key))
                 .ToList();
             List<ProgramScheduleItem> fakeScheduleItems = [];
-
-            // this will be used to clone a schedule item
-            MethodInfo generic = typeof(JsonConvert).GetMethods()
-                .FirstOrDefault(x => x.Name.Equals("DeserializeObject", StringComparison.OrdinalIgnoreCase) &&
-                                     x.IsGenericMethod &&
-                                     x.GetParameters().Length == 1)?.MakeGenericMethod(scheduleItem.GetType());
-
             foreach (CollectionWithItems fakeCollection in fakeCollections)
             {
                 CollectionKey key = (fakeCollection.ShowId, fakeCollection.ArtistId, fakeCollection.Key) switch
@@ -709,8 +701,7 @@ public class PlayoutBuilder : IPlayoutBuilder
                     continue;
                 }
 
-                string serialized = JsonConvert.SerializeObject(scheduleItem);
-                var copyScheduleItem = generic.Invoke(this, [serialized]) as ProgramScheduleItem;
+                var copyScheduleItem = scheduleItem.DeepCopy();
                 copyScheduleItem.CollectionType = key.CollectionType;
                 copyScheduleItem.MediaItemId = key.MediaItemId;
                 copyScheduleItem.FakeCollectionKey = key.FakeCollectionKey;