diff --git a/src/NexusMods.App.UI/Controls/Spine/SpineViewModel.cs b/src/NexusMods.App.UI/Controls/Spine/SpineViewModel.cs
index 1d799a2244..ca21302ac7 100644
--- a/src/NexusMods.App.UI/Controls/Spine/SpineViewModel.cs
+++ b/src/NexusMods.App.UI/Controls/Spine/SpineViewModel.cs
@@ -75,6 +75,7 @@ public SpineViewModel(ILogger<SpineViewModel> logger,
         this.WhenActivated(disposables =>
         {
             router.Messages
+                .OnUI()
                 .SubscribeWithErrorLogging(logger, HandleMessage)
                 .DisposeWith(disposables);
 
diff --git a/src/NexusMods.App.UI/RightContent/FoundGamesViewModel.cs b/src/NexusMods.App.UI/RightContent/FoundGamesViewModel.cs
index a166ef5516..ec91a96c76 100644
--- a/src/NexusMods.App.UI/RightContent/FoundGamesViewModel.cs
+++ b/src/NexusMods.App.UI/RightContent/FoundGamesViewModel.cs
@@ -52,10 +52,7 @@ public void InitializeFromFound(IEnumerable<IGame> games)
                 vm.Installation = install;
                 vm.PrimaryButton = ReactiveCommand.CreateFromTask(async () =>
                 {
-                    await Task.Run(async () =>
-                    {
-                        await ManageGame(install);
-                    });
+                    await Task.Run(async () => await ManageGame(install));
                 });
                 return vm;
             });
diff --git a/src/NexusMods.DataModel/LoadoutSynchronizer/ALoadoutSynchronizer.cs b/src/NexusMods.DataModel/LoadoutSynchronizer/ALoadoutSynchronizer.cs
index c4d8f375b6..fb7d885ebc 100644
--- a/src/NexusMods.DataModel/LoadoutSynchronizer/ALoadoutSynchronizer.cs
+++ b/src/NexusMods.DataModel/LoadoutSynchronizer/ALoadoutSynchronizer.cs
@@ -8,6 +8,7 @@
 using NexusMods.DataModel.Loadouts.LoadoutSynchronizerDTOs;
 using NexusMods.DataModel.Loadouts.ModFiles;
 using NexusMods.DataModel.Loadouts.Mods;
+using NexusMods.DataModel.LoadoutSynchronizer.Exceptions;
 using NexusMods.DataModel.Sorting;
 using NexusMods.DataModel.Sorting.Rules;
 using NexusMods.FileExtractor.StreamFactories;
@@ -252,7 +253,7 @@ public virtual async Task<DiskState> GetDiskState(GameInstallation installation)
     /// <param name="entry"></param>
     public virtual void HandleNeedIngest(HashedEntry entry)
     {
-        throw new Exception("File changed during apply, need to ingest");
+        throw new NeedsIngestException();
     }
 
     /// <inheritdoc />
diff --git a/src/NexusMods.DataModel/LoadoutSynchronizer/Exceptions/NeedsIngestException.cs b/src/NexusMods.DataModel/LoadoutSynchronizer/Exceptions/NeedsIngestException.cs
new file mode 100644
index 0000000000..d17675b281
--- /dev/null
+++ b/src/NexusMods.DataModel/LoadoutSynchronizer/Exceptions/NeedsIngestException.cs
@@ -0,0 +1,16 @@
+namespace NexusMods.DataModel.LoadoutSynchronizer.Exceptions;
+
+/// <summary>
+/// Thrown when there are changes in the game folder that need to be ingested before a loadout can be applied
+/// </summary>
+public class NeedsIngestException : Exception
+{
+    /// <summary>
+    /// Thrown when a loadout needs to be ingested before it can be applied
+    /// </summary>
+    public NeedsIngestException() : base("Loadout needs to be ingested before it can be applied")
+    {
+
+    }
+
+}
diff --git a/src/NexusMods.DataModel/ToolManager.cs b/src/NexusMods.DataModel/ToolManager.cs
index c1aa7bfa1b..7c8167370e 100644
--- a/src/NexusMods.DataModel/ToolManager.cs
+++ b/src/NexusMods.DataModel/ToolManager.cs
@@ -1,8 +1,10 @@
-using NexusMods.DataModel.Abstractions;
+using Microsoft.Extensions.Logging;
+using NexusMods.DataModel.Abstractions;
 using NexusMods.DataModel.Games;
 using NexusMods.DataModel.Loadouts;
 using NexusMods.DataModel.Loadouts.Extensions;
 using NexusMods.DataModel.Loadouts.Mods;
+using NexusMods.DataModel.LoadoutSynchronizer.Exceptions;
 
 namespace NexusMods.DataModel;
 
@@ -14,6 +16,7 @@ public class ToolManager : IToolManager
     private readonly ILookup<GameDomain,ITool> _tools;
     private readonly IDataStore _dataStore;
     private readonly LoadoutRegistry _loadoutRegistry;
+    private readonly ILogger<ToolManager> _logger;
 
     /// <summary>
     /// DI Constructor
@@ -22,8 +25,9 @@ public class ToolManager : IToolManager
     /// <param name="loadoutSynchronizer"></param>
     /// <param name="dataStore"></param>
     /// <param name="loadoutRegistry"></param>
-    public ToolManager(IEnumerable<ITool> tools, IDataStore dataStore, LoadoutRegistry loadoutRegistry)
+    public ToolManager(ILogger<ToolManager> logger, IEnumerable<ITool> tools, IDataStore dataStore, LoadoutRegistry loadoutRegistry)
     {
+        _logger = logger;
         _dataStore = dataStore;
         _tools = tools.SelectMany(tool => tool.Domains.Select(domain => (domain, tool)))
             .ToLookup(t => t.domain, t => t.tool);
@@ -43,10 +47,23 @@ public async Task<Loadout> RunTool(ITool tool, Loadout loadout, ModId? generated
         if (!tool.Domains.Contains(loadout.Installation.Game.Domain))
             throw new Exception("Tool does not support this game");
 
-        await loadout.Apply();
+        _logger.LogInformation("Applying loadout {LoadoutId} to {GameName} {GameVersion}", loadout.LoadoutId, loadout.Installation.Game.Name, loadout.Installation.Version);
+        try
+        {
+            await loadout.Apply();
+        }
+        catch (NeedsIngestException)
+        {
+            _logger.LogInformation("Ingesting loadout {LoadoutId} from {GameName} {GameVersion}", loadout.LoadoutId, loadout.Installation.Game.Name, loadout.Installation.Version);
+            await loadout.Ingest();
+            _logger.LogInformation("Applying loadout {LoadoutId} to {GameName} {GameVersion}", loadout.LoadoutId, loadout.Installation.Game.Name, loadout.Installation.Version);
+            await loadout.Apply();
+        }
 
+        _logger.LogInformation("Running tool {ToolName} for loadout {LoadoutId} on {GameName} {GameVersion}", tool.Name, loadout.LoadoutId, loadout.Installation.Game.Name, loadout.Installation.Version);
         await tool.Execute(loadout, token);
 
+        _logger.LogInformation("Ingesting loadout {LoadoutId} from {GameName} {GameVersion}", loadout.LoadoutId, loadout.Installation.Game.Name, loadout.Installation.Version);
         return await loadout.Ingest();
     }
 }