diff --git a/CHANGELOG.md b/CHANGELOG.md
index 880e0dc5..596aa806 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -56,6 +56,7 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/).
 - Fix multi-variant playlist to report more accurate `BANDWIDTH` value based on ffmpeg profile
 - Fix detecting NVIDIA capabilities on Blackwell GPUs
 - Fix decoder selection in NVIDIA pipeline
+- Prevent playback order `Shuffle In Order` from being used with `Fill With Group Mode` as they are incompatible
 
 ## [25.1.0] - 2025-01-10
 ### Added
diff --git a/ErsatzTV.Application/ProgramSchedules/Commands/ReplaceProgramScheduleItemsHandler.cs b/ErsatzTV.Application/ProgramSchedules/Commands/ReplaceProgramScheduleItemsHandler.cs
index bcae69d6..8c0c8e2f 100644
--- a/ErsatzTV.Application/ProgramSchedules/Commands/ReplaceProgramScheduleItemsHandler.cs
+++ b/ErsatzTV.Application/ProgramSchedules/Commands/ReplaceProgramScheduleItemsHandler.cs
@@ -99,6 +99,12 @@ public class ReplaceProgramScheduleItemsHandler : ProgramScheduleItemCommandBase
         var keyOrders = new Dictionary<CollectionKey, System.Collections.Generic.HashSet<PlaybackOrder>>();
         foreach (ReplaceProgramScheduleItem item in request.Items)
         {
+            if (item.PlaybackOrder is PlaybackOrder.ShuffleInOrder &&
+                item.FillWithGroupMode is not FillWithGroupMode.None)
+            {
+                return new BaseError("Shuffle in Order cannot be used with Fill With Group Mode");
+            }
+
             var key = new CollectionKey(
                 item.CollectionType,
                 item.CollectionId,
diff --git a/ErsatzTV.Application/ProgramSchedules/Queries/GetProgramScheduleItemsHandler.cs b/ErsatzTV.Application/ProgramSchedules/Queries/GetProgramScheduleItemsHandler.cs
index dd98442b..15e4343c 100644
--- a/ErsatzTV.Application/ProgramSchedules/Queries/GetProgramScheduleItemsHandler.cs
+++ b/ErsatzTV.Application/ProgramSchedules/Queries/GetProgramScheduleItemsHandler.cs
@@ -72,6 +72,11 @@ public class GetProgramScheduleItemsHandler :
                     item = item with { PlayoutMode = PlayoutMode.One };
                 }
             }
+
+            if (item.PlaybackOrder is PlaybackOrder.ShuffleInOrder)
+            {
+                item = item with { FillWithGroupMode = FillWithGroupMode.None };
+            }
         }
 
         return item;
diff --git a/ErsatzTV/Pages/ScheduleItemsEditor.razor b/ErsatzTV/Pages/ScheduleItemsEditor.razor
index d14e9a5d..54bc0a7e 100644
--- a/ErsatzTV/Pages/ScheduleItemsEditor.razor
+++ b/ErsatzTV/Pages/ScheduleItemsEditor.razor
@@ -282,8 +282,15 @@
                 </MudGrid>
                 <MudSelect Class="mt-3" Label="Fill With Group Mode (Show or Artist)" @bind-Value="@_selectedItem.FillWithGroupMode" For="@(() => _selectedItem.FillWithGroupMode)" Disabled="@(_selectedItem.CanFillWithGroups == false)">
                     <MudSelectItem Value="FillWithGroupMode.None">(none)</MudSelectItem>
-                    <MudSelectItem Value="FillWithGroupMode.FillWithOrderedGroups">Ordered Groups</MudSelectItem>
-                    <MudSelectItem Value="FillWithGroupMode.FillWithShuffledGroups">Shuffled Groups</MudSelectItem>
+                    @if (_selectedItem.CanFillWithGroups)
+                    {
+                        <MudSelectItem Value="FillWithGroupMode.FillWithOrderedGroups">Ordered Groups</MudSelectItem>
+                        <MudSelectItem Value="FillWithGroupMode.FillWithShuffledGroups">Shuffled Groups</MudSelectItem>
+                    }
+                    else
+                    {
+                        _selectedItem.FillWithGroupMode = FillWithGroupMode.None;
+                    }
                 </MudSelect>
                 <MudSelect Class="mt-3" Label="Tail Mode" @bind-Value="@_selectedItem.TailMode" For="@(() => _selectedItem.TailMode)" Disabled="@(_selectedItem.PlayoutMode != PlayoutMode.Duration)">
                     <MudSelectItem Value="@TailMode.None">(none)</MudSelectItem>
diff --git a/ErsatzTV/ViewModels/ProgramScheduleItemEditViewModel.cs b/ErsatzTV/ViewModels/ProgramScheduleItemEditViewModel.cs
index 28e889fc..624af3d0 100644
--- a/ErsatzTV/ViewModels/ProgramScheduleItemEditViewModel.cs
+++ b/ErsatzTV/ViewModels/ProgramScheduleItemEditViewModel.cs
@@ -41,6 +41,7 @@ public class ProgramScheduleItemEditViewModel : INotifyPropertyChanged
 
     public bool CanFillWithGroups =>
         PlayoutMode is PlayoutMode.Multiple or PlayoutMode.Duration
+        && PlaybackOrder is not PlaybackOrder.ShuffleInOrder
         && CollectionType is ProgramScheduleItemCollectionType.Collection
             or ProgramScheduleItemCollectionType.MultiCollection or ProgramScheduleItemCollectionType.SmartCollection;