diff --git a/Pinta.Core/Actions/EditActions.cs b/Pinta.Core/Actions/EditActions.cs
index c0dc0757cd..b1bad74291 100644
--- a/Pinta.Core/Actions/EditActions.cs
+++ b/Pinta.Core/Actions/EditActions.cs
@@ -321,7 +321,8 @@ private void HandlePintaCoreActionsEditFillSelectionActivated (object sender, Ev
 				Translations.GetString ("Fill Selection"),
 				old,
 				doc.Layers.CurrentUserLayerIndex
-			)
+			),
+			this
 		);
 	}
 
@@ -341,7 +342,7 @@ private void HandlePintaCoreActionsEditSelectAllActivated (object sender, EventA
 		doc.ResetSelectionPaths ();
 		doc.Selection.Visible = true;
 
-		doc.History.PushNewItem (hist);
+		doc.History.PushNewItem (hist, this);
 		doc.Workspace.Invalidate ();
 	}
 
@@ -367,7 +368,8 @@ private void HandlePintaCoreActionsEditEraseSelectionActivated (object sender, E
 			sender switch {
 				string and "Cut" => new SimpleHistoryItem (Resources.StandardIcons.EditCut, Translations.GetString ("Cut"), old, doc.Layers.CurrentUserLayerIndex),
 				_ => new SimpleHistoryItem (Resources.Icons.EditSelectionErase, Translations.GetString ("Erase Selection"), old, doc.Layers.CurrentUserLayerIndex),
-			}
+			},
+			this
 		);
 	}
 
@@ -386,7 +388,7 @@ private void HandlePintaCoreActionsEditDeselectActivated (object sender, EventAr
 
 		doc.ResetSelectionPaths ();
 
-		doc.History.PushNewItem (hist);
+		doc.History.PushNewItem (hist, this);
 		doc.Workspace.Invalidate ();
 	}
 
@@ -456,7 +458,7 @@ private void HandlerPintaCoreActionsEditUndoActivated (object sender, EventArgs
 		if (tools.CurrentTool?.DoHandleUndo (doc) == true)
 			return;
 
-		doc.History.Undo ();
+		doc.History.Undo (this);
 
 		tools.CurrentTool?.DoAfterUndo (doc);
 	}
@@ -468,7 +470,7 @@ private void HandlerPintaCoreActionsEditRedoActivated (object sender, EventArgs
 		if (tools.CurrentTool?.DoHandleRedo (doc) == true)
 			return;
 
-		doc.History.Redo ();
+		doc.History.Redo (this);
 
 		tools.CurrentTool?.DoAfterRedo (doc);
 	}
@@ -610,7 +612,7 @@ void HandleInvertSelectionActivated (object sender, EventArgs e)
 
 		doc.Selection.Invert (doc.ImageSize);
 
-		doc.History.PushNewItem (historyItem);
+		doc.History.PushNewItem (historyItem, this);
 		doc.Workspace.Invalidate ();
 	}
 
diff --git a/Pinta.Core/Actions/ImageActions.cs b/Pinta.Core/Actions/ImageActions.cs
index 195e5fe758..46a7baf212 100644
--- a/Pinta.Core/Actions/ImageActions.cs
+++ b/Pinta.Core/Actions/ImageActions.cs
@@ -44,11 +44,13 @@ public sealed class ImageActions
 
 	private readonly ToolManager tools;
 	private readonly WorkspaceManager workspace;
+	private readonly EditActions edit;
 	private readonly ViewActions view;
 
 	public ImageActions (
 		ToolManager tools,
 		WorkspaceManager workspace,
+		EditActions edit,
 		ViewActions view)
 	{
 		CropToSelection = new Command (
@@ -121,6 +123,7 @@ public ImageActions (
 
 		this.tools = tools;
 		this.workspace = workspace;
+		this.edit = edit;
 		this.view = view;
 	}
 
@@ -191,7 +194,7 @@ private void HandlePintaCoreActionsImageRotateCCWActivated (object sender, Event
 		tools.Commit ();
 
 		doc.RotateImageCCW ();
-		doc.History.PushNewItem (new InvertHistoryItem (InvertType.Rotate90CCW));
+		doc.History.PushNewItem (new InvertHistoryItem (InvertType.Rotate90CCW), edit);
 	}
 
 	private void HandlePintaCoreActionsImageRotateCWActivated (object sender, EventArgs e)
@@ -201,7 +204,7 @@ private void HandlePintaCoreActionsImageRotateCWActivated (object sender, EventA
 		tools.Commit ();
 
 		doc.RotateImageCW ();
-		doc.History.PushNewItem (new InvertHistoryItem (InvertType.Rotate90CW));
+		doc.History.PushNewItem (new InvertHistoryItem (InvertType.Rotate90CW), edit);
 	}
 
 	private void HandlePintaCoreActionsImageFlattenActivated (object sender, EventArgs e)
@@ -227,7 +230,7 @@ private void HandlePintaCoreActionsImageFlattenActivated (object sender, EventAr
 
 		hist.Push (new SimpleHistoryItem (string.Empty, string.Empty, oldBottomSurface, 0));
 
-		doc.History.PushNewItem (hist);
+		doc.History.PushNewItem (hist, edit);
 	}
 
 	private void HandlePintaCoreActionsImageRotate180Activated (object sender, EventArgs e)
@@ -237,7 +240,7 @@ private void HandlePintaCoreActionsImageRotate180Activated (object sender, Event
 		tools.Commit ();
 
 		doc.RotateImage180 ();
-		doc.History.PushNewItem (new InvertHistoryItem (InvertType.Rotate180));
+		doc.History.PushNewItem (new InvertHistoryItem (InvertType.Rotate180), edit);
 	}
 
 	private void HandlePintaCoreActionsImageFlipVerticalActivated (object sender, EventArgs e)
@@ -247,7 +250,7 @@ private void HandlePintaCoreActionsImageFlipVerticalActivated (object sender, Ev
 		tools.Commit ();
 
 		doc.FlipImageVertical ();
-		doc.History.PushNewItem (new InvertHistoryItem (InvertType.FlipVertical));
+		doc.History.PushNewItem (new InvertHistoryItem (InvertType.FlipVertical), edit);
 	}
 
 	private void HandlePintaCoreActionsImageFlipHorizontalActivated (object sender, EventArgs e)
@@ -257,7 +260,7 @@ private void HandlePintaCoreActionsImageFlipHorizontalActivated (object sender,
 		tools.Commit ();
 
 		doc.FlipImageHorizontal ();
-		doc.History.PushNewItem (new InvertHistoryItem (InvertType.FlipHorizontal));
+		doc.History.PushNewItem (new InvertHistoryItem (InvertType.FlipHorizontal), edit);
 	}
 
 	private void HandlePintaCoreActionsImageCropToSelectionActivated (object sender, EventArgs e)
@@ -300,7 +303,7 @@ void CropImageToRectangle (Document doc, RectangleI rect, Path? selection)
 		double original_scale = doc.Workspace.Scale;
 		doc.ImageSize = rect.Size;
 		doc.Workspace.ViewSize = rect.Size;
-		doc.Workspace.Scale = original_scale;
+		doc.Workspace.SetScale (original_scale);
 
 		view.UpdateCanvasScale ();
 
@@ -309,7 +312,7 @@ void CropImageToRectangle (Document doc, RectangleI rect, Path? selection)
 
 		hist.FinishSnapshotOfImage ();
 
-		doc.History.PushNewItem (hist);
+		doc.History.PushNewItem (hist, edit);
 		doc.ResetSelectionPaths ();
 
 		doc.Workspace.Invalidate ();
diff --git a/Pinta.Core/Actions/LayerActions.cs b/Pinta.Core/Actions/LayerActions.cs
index f6c9fade92..8dfd07ba8b 100644
--- a/Pinta.Core/Actions/LayerActions.cs
+++ b/Pinta.Core/Actions/LayerActions.cs
@@ -47,6 +47,7 @@ public sealed class LayerActions
 	private readonly RecentFileManager recent_files;
 	private readonly ToolManager tools;
 	private readonly WorkspaceManager workspace;
+	private readonly EditActions edit;
 	private readonly ImageActions image;
 	public LayerActions (
 		ChromeManager chrome,
@@ -54,6 +55,7 @@ public LayerActions (
 		RecentFileManager recentFiles,
 		ToolManager tools,
 		WorkspaceManager workspace,
+		EditActions edit,
 		ImageActions image)
 	{
 		AddNewLayer = new Command (
@@ -132,6 +134,7 @@ public LayerActions (
 		recent_files = recentFiles;
 		this.tools = tools;
 		this.workspace = workspace;
+		this.edit = edit;
 		this.image = image;
 	}
 
@@ -261,7 +264,7 @@ private async void HandlePintaCoreActionsLayersImportFromFileActivated (object s
 		// --- Changes to document go after everything else is completed successfully
 
 		doc.Layers.SetCurrentUserLayer (layer);
-		doc.History.PushNewItem (hist);
+		doc.History.PushNewItem (hist, edit);
 		doc.Workspace.Invalidate ();
 	}
 
@@ -273,7 +276,7 @@ private void HandlePintaCoreActionsLayersFlipVerticalActivated (object sender, E
 
 		doc.Layers.CurrentUserLayer.FlipVertical ();
 		doc.Workspace.Invalidate ();
-		doc.History.PushNewItem (new InvertHistoryItem (InvertType.FlipLayerVertical, doc.Layers.CurrentUserLayerIndex));
+		doc.History.PushNewItem (new InvertHistoryItem (InvertType.FlipLayerVertical, doc.Layers.CurrentUserLayerIndex), edit);
 	}
 
 	private void HandlePintaCoreActionsLayersFlipHorizontalActivated (object sender, EventArgs e)
@@ -284,7 +287,7 @@ private void HandlePintaCoreActionsLayersFlipHorizontalActivated (object sender,
 
 		doc.Layers.CurrentUserLayer.FlipHorizontal ();
 		doc.Workspace.Invalidate ();
-		doc.History.PushNewItem (new InvertHistoryItem (InvertType.FlipLayerHorizontal, doc.Layers.CurrentUserLayerIndex));
+		doc.History.PushNewItem (new InvertHistoryItem (InvertType.FlipLayerHorizontal, doc.Layers.CurrentUserLayerIndex), edit);
 	}
 
 	private void HandlePintaCoreActionsLayersMoveLayerUpActivated (object sender, EventArgs e)
@@ -300,7 +303,7 @@ private void HandlePintaCoreActionsLayersMoveLayerUpActivated (object sender, Ev
 			doc.Layers.CurrentUserLayerIndex + 1);
 
 		doc.Layers.MoveCurrentLayerUp ();
-		doc.History.PushNewItem (hist);
+		doc.History.PushNewItem (hist, edit);
 	}
 
 	private void HandlePintaCoreActionsLayersMoveLayerDownActivated (object sender, EventArgs e)
@@ -316,7 +319,7 @@ private void HandlePintaCoreActionsLayersMoveLayerDownActivated (object sender,
 			doc.Layers.CurrentUserLayerIndex - 1);
 
 		doc.Layers.MoveCurrentLayerDown ();
-		doc.History.PushNewItem (hist);
+		doc.History.PushNewItem (hist, edit);
 	}
 
 	private void HandlePintaCoreActionsLayersMergeLayerDownActivated (object sender, EventArgs e)
@@ -348,7 +351,7 @@ private void HandlePintaCoreActionsLayersMergeLayerDownActivated (object sender,
 		hist.Push (h1);
 		hist.Push (h2);
 
-		doc.History.PushNewItem (hist);
+		doc.History.PushNewItem (hist, edit);
 	}
 
 	private void HandlePintaCoreActionsLayersDuplicateLayerActivated (object sender, EventArgs e)
@@ -366,7 +369,7 @@ private void HandlePintaCoreActionsLayersDuplicateLayerActivated (object sender,
 			Resources.Icons.LayerDuplicate,
 			Translations.GetString ("Duplicate Layer"),
 			doc.Layers.IndexOf (l));
-		doc.History.PushNewItem (hist);
+		doc.History.PushNewItem (hist, edit);
 	}
 
 	private void HandlePintaCoreActionsLayersDeleteLayerActivated (object sender, EventArgs e)
@@ -383,7 +386,7 @@ private void HandlePintaCoreActionsLayersDeleteLayerActivated (object sender, Ev
 
 		doc.Layers.DeleteLayer (doc.Layers.CurrentUserLayerIndex);
 
-		doc.History.PushNewItem (hist);
+		doc.History.PushNewItem (hist, edit);
 	}
 
 	private void HandlePintaCoreActionsLayersAddNewLayerActivated (object sender, EventArgs e)
@@ -400,6 +403,6 @@ private void HandlePintaCoreActionsLayersAddNewLayerActivated (object sender, Ev
 			Resources.Icons.LayerNew,
 			Translations.GetString ("Add New Layer"),
 			doc.Layers.IndexOf (l));
-		doc.History.PushNewItem (hist);
+		doc.History.PushNewItem (hist, edit);
 	}
 }
diff --git a/Pinta.Core/Classes/Document.cs b/Pinta.Core/Classes/Document.cs
index c2143a62b8..4be18bf85b 100644
--- a/Pinta.Core/Classes/Document.cs
+++ b/Pinta.Core/Classes/Document.cs
@@ -197,7 +197,7 @@ public void ClearFileReference ()
 	public void Close ()
 	{
 		Layers.Close ();
-		Workspace.History.Clear ();
+		Workspace.History.Clear (actions.Edit);
 	}
 
 	public Context CreateClippedContext ()
@@ -233,7 +233,7 @@ public void FinishSelection ()
 		Layers.DestroySelectionLayer ();
 		Workspace.Invalidate ();
 
-		Workspace.History.PushNewItem (hist);
+		Workspace.History.PushNewItem (hist, actions.Edit);
 	}
 
 	// Flip image horizontally
@@ -341,11 +341,11 @@ public void ResizeCanvas (
 		if (compoundAction is not null)
 			compoundAction.Push (hist);
 		else
-			Workspace.History.PushNewItem (hist);
+			Workspace.History.PushNewItem (hist, actions.Edit);
 
 		ResetSelectionPaths ();
 
-		Workspace.Scale = scale;
+		Workspace.SetScale (scale);
 	}
 
 	public void ResizeImage (
@@ -370,11 +370,11 @@ public void ResizeImage (
 
 		hist.FinishSnapshotOfImage ();
 
-		Workspace.History.PushNewItem (hist);
+		Workspace.History.PushNewItem (hist, actions.Edit);
 
 		ResetSelectionPaths ();
 
-		Workspace.Scale = scale;
+		Workspace.SetScale (scale);
 		actions.View.UpdateCanvasScale ();
 	}
 
diff --git a/Pinta.Core/Classes/DocumentHistory.cs b/Pinta.Core/Classes/DocumentHistory.cs
index 402babbf50..fdf734edd2 100644
--- a/Pinta.Core/Classes/DocumentHistory.cs
+++ b/Pinta.Core/Classes/DocumentHistory.cs
@@ -31,8 +31,6 @@ namespace Pinta.Core;
 
 public sealed class DocumentHistory
 {
-	private readonly EditActions edit;
-
 	private readonly Document document;
 
 	private readonly List<BaseHistoryItem> history = [];
@@ -42,11 +40,8 @@ public sealed class DocumentHistory
 	public event EventHandler? ActionUndone;
 	public event EventHandler? ActionRedone;
 
-	internal DocumentHistory (
-		EditActions edit,
-		Document document)
+	internal DocumentHistory (Document document)
 	{
-		this.edit = edit;
 		this.document = document;
 	}
 
@@ -63,7 +58,7 @@ internal DocumentHistory (
 
 	public IEnumerable<BaseHistoryItem> Items => history;
 
-	public void PushNewItem (BaseHistoryItem newItem)
+	public void PushNewItem (BaseHistoryItem newItem, EditActions edit)
 	{
 		// Remove all old redos starting from the end of the list
 		for (var i = history.Count - 1; i >= 0; i--) {
@@ -89,7 +84,7 @@ public void PushNewItem (BaseHistoryItem newItem)
 		HistoryItemAdded?.Invoke (this, new HistoryItemAddedEventArgs (newItem));
 	}
 
-	public void Undo ()
+	public void Undo (EditActions edit)
 	{
 		if (Pointer < 0)
 			throw new InvalidOperationException ("Undo stack is empty");
@@ -114,7 +109,7 @@ public void Undo ()
 		ActionUndone?.Invoke (this, EventArgs.Empty);
 	}
 
-	public void Redo ()
+	public void Redo (EditActions edit)
 	{
 		if (Pointer >= history.Count - 1)
 			throw new InvalidOperationException ("Redo stack is empty");
@@ -160,7 +155,7 @@ public void SetDirty ()
 		document.IsDirty = true;
 	}
 
-	public void Clear ()
+	public void Clear (EditActions edit)
 	{
 		history.Clear ();
 		Pointer = -1;
diff --git a/Pinta.Core/Classes/DocumentWorkspace.cs b/Pinta.Core/Classes/DocumentWorkspace.cs
index b9af931a07..e8e5e30bfa 100644
--- a/Pinta.Core/Classes/DocumentWorkspace.cs
+++ b/Pinta.Core/Classes/DocumentWorkspace.cs
@@ -30,9 +30,8 @@ namespace Pinta.Core;
 
 public sealed class DocumentWorkspace
 {
-	private readonly Document document;
-
 	private readonly ActionManager actions;
+	private readonly Document document;
 
 	private enum ZoomType
 	{
@@ -41,15 +40,11 @@ private enum ZoomType
 		ZoomManually,
 	}
 
-	internal DocumentWorkspace (
-		ActionManager actions,
-		Document document)
+	internal DocumentWorkspace (ActionManager actions, Document document)
 	{
 		this.actions = actions;
-
 		this.document = document;
-
-		History = new DocumentHistory (actions.Edit, document);
+		History = new DocumentHistory (document);
 	}
 
 	#region Public Events
@@ -103,17 +98,18 @@ public bool ImageFitsInWindow {
 	/// <summary>
 	/// Scale factor for the zoomed image.
 	/// </summary>
-	public double Scale {
-		get => ViewSize.Width / (double) document.ImageSize.Width;
-		set {
-			if (value == ViewSize.Width / (double) document.ImageSize.Width && value == ViewSize.Height / (double) document.ImageSize.Height)
-				return;
+	public double Scale
+		=> ViewSize.Width / (double) document.ImageSize.Width;
+
+	public void SetScale (double value)
+	{
+		if (value == ViewSize.Width / (double) document.ImageSize.Width && value == ViewSize.Height / (double) document.ImageSize.Height)
+			return;
 
-			document.ImageSize = CoercedToPositive (document.ImageSize);
-			ViewSize = GetNewViewSize (document.ImageSize, value);
+		document.ImageSize = CoercedToPositive (document.ImageSize);
+		ViewSize = GetNewViewSize (document.ImageSize, value);
 
-			Invalidate ();
-		}
+		Invalidate ();
 	}
 
 	/// <summary>
diff --git a/Pinta.Core/Managers/ActionManager.cs b/Pinta.Core/Managers/ActionManager.cs
index 910936178a..25ce6d531c 100644
--- a/Pinta.Core/Managers/ActionManager.cs
+++ b/Pinta.Core/Managers/ActionManager.cs
@@ -66,8 +66,8 @@ public ActionManager (
 
 		FileActions file = new (system, app);
 		HelpActions help = new (system, app);
-		ImageActions image = new (tools, workspace, view);
-		LayerActions layers = new (chrome, imageFormats, recentFiles, tools, workspace, image);
+		ImageActions image = new (tools, workspace, edit, view);
+		LayerActions layers = new (chrome, imageFormats, recentFiles, tools, workspace, edit, image);
 
 		// --- References to keep
 
diff --git a/Pinta.Core/Managers/LivePreviewManager.cs b/Pinta.Core/Managers/LivePreviewManager.cs
index 3a65f5958b..8c4c2a0c43 100644
--- a/Pinta.Core/Managers/LivePreviewManager.cs
+++ b/Pinta.Core/Managers/LivePreviewManager.cs
@@ -44,12 +44,14 @@ public interface ILivePreview
 
 public sealed class LivePreviewManager : ILivePreview
 {
+	private readonly ActionManager actions;
 	private readonly WorkspaceManager workspace;
 	private readonly ToolManager tools;
 	private readonly SystemManager system;
 	private readonly ChromeManager chrome;
 
 	internal LivePreviewManager (
+		ActionManager actions,
 		WorkspaceManager workspaceManager,
 		ToolManager toolManager,
 		SystemManager systemManager,
@@ -57,6 +59,7 @@ internal LivePreviewManager (
 	{
 		IsEnabled = false;
 
+		this.actions = actions;
 		workspace = workspaceManager;
 		tools = toolManager;
 		system = systemManager;
@@ -181,7 +184,7 @@ public async void Start (BaseEffect effect)
 			layer.DrawWithOperator (context, LivePreviewSurface, Cairo.Operator.Source);
 			context.Restore ();
 
-			workspace.ActiveDocument.History.PushNewItem (historyItem);
+			workspace.ActiveDocument.History.PushNewItem (historyItem, actions.Edit);
 
 		} finally {
 
diff --git a/Pinta.Core/Managers/WorkspaceManager.cs b/Pinta.Core/Managers/WorkspaceManager.cs
index 97e0b03328..2bc17bd32f 100644
--- a/Pinta.Core/Managers/WorkspaceManager.cs
+++ b/Pinta.Core/Managers/WorkspaceManager.cs
@@ -136,7 +136,7 @@ public static Document NewDocument (
 			g.Paint ();
 		}
 
-		doc.Workspace.History.PushNewItem (new BaseHistoryItem (Resources.StandardIcons.DocumentNew, Translations.GetString ("New Image")));
+		doc.Workspace.History.PushNewItem (new BaseHistoryItem (Resources.StandardIcons.DocumentNew, Translations.GetString ("New Image")), PintaCore.Actions.Edit);
 		doc.Workspace.History.SetClean ();
 
 		return doc;
@@ -203,7 +203,7 @@ public Size CanvasSize {
 
 	public double Scale {
 		get => ActiveWorkspace.Scale;
-		set => ActiveWorkspace.Scale = value;
+		set => ActiveWorkspace.SetScale (value);
 	}
 
 	private readonly List<Document> open_documents;
@@ -348,7 +348,7 @@ public bool OpenFile (
 				}
 			}
 
-			ActiveWorkspace.History.PushNewItem (new BaseHistoryItem (Resources.StandardIcons.DocumentOpen, Translations.GetString ("Open Image")));
+			ActiveWorkspace.History.PushNewItem (new BaseHistoryItem (Resources.StandardIcons.DocumentOpen, Translations.GetString ("Open Image")), PintaCore.Actions.Edit);
 			ActiveDocument.History.SetClean ();
 
 			return true;
diff --git a/Pinta.Core/PintaCore.cs b/Pinta.Core/PintaCore.cs
index abdba7e115..802d05bc0c 100644
--- a/Pinta.Core/PintaCore.cs
+++ b/Pinta.Core/PintaCore.cs
@@ -82,7 +82,7 @@ static PintaCore ()
 		ToolManager tools = new (workspace, chrome);
 		PaletteManager palette = new (settings, paletteFormats);
 		ActionManager actions = new (chrome, imageFormats, paletteFormats, palette, recentFiles, system, tools, workspace);
-		LivePreviewManager livePreview = new (workspace, tools, system, chrome);
+		LivePreviewManager livePreview = new (actions, workspace, tools, system, chrome);
 		EffectsManager effects = new (actions, chrome, livePreview);
 		CanvasGridManager canvasGrid = new (workspace, settings);
 
diff --git a/Pinta.Gui.Widgets/Widgets/History/HistoryListView.cs b/Pinta.Gui.Widgets/Widgets/History/HistoryListView.cs
index ae5d755123..f8ec682a6b 100644
--- a/Pinta.Gui.Widgets/Widgets/History/HistoryListView.cs
+++ b/Pinta.Gui.Widgets/Widgets/History/HistoryListView.cs
@@ -38,7 +38,9 @@ public sealed class HistoryListView : Gtk.ScrolledWindow
 
 	private Document? active_document;
 
-	public HistoryListView ()
+	private readonly EditActions edit;
+
+	public HistoryListView (EditActions edit)
 	{
 		Gio.ListStore listModel = Gio.ListStore.New (HistoryListViewItem.GetGType ());
 
@@ -79,6 +81,8 @@ public HistoryListView ()
 		// --- Event handlers for the application
 		// TODO: Move handlers out of this constructor
 
+		this.edit = edit;
+
 		PintaCore.Workspace.ActiveDocumentChanged += OnActiveDocumentChanged;
 	}
 
@@ -89,10 +93,10 @@ private void HandleSelectionChanged (Gtk.SelectionModel sender, EventArgs e)
 		int index = (int) selection_model.Selected;
 
 		while (active_document.History.Pointer < index)
-			active_document.History.Redo ();
+			active_document.History.Redo (edit);
 
 		while (active_document.History.Pointer > index)
-			active_document.History.Undo ();
+			active_document.History.Undo (edit);
 	}
 
 	private void OnActiveDocumentChanged (object? sender, EventArgs e)
diff --git a/Pinta.Gui.Widgets/Widgets/Layers/LayersListViewItemWidget.cs b/Pinta.Gui.Widgets/Widgets/Layers/LayersListViewItemWidget.cs
index d229e59c72..032723b978 100644
--- a/Pinta.Gui.Widgets/Widgets/Layers/LayersListViewItemWidget.cs
+++ b/Pinta.Gui.Widgets/Widgets/Layers/LayersListViewItemWidget.cs
@@ -104,7 +104,7 @@ public void HandleVisibilityToggled (bool visible)
 
 		historyItem.Redo ();
 
-		doc.History.PushNewItem (historyItem);
+		doc.History.PushNewItem (historyItem, PintaCore.Actions.Edit);
 	}
 
 	public event EventHandler? LayerModified;
diff --git a/Pinta.Tools/Editable/EditEngines/BaseEditEngine.cs b/Pinta.Tools/Editable/EditEngines/BaseEditEngine.cs
index 22c638b9a6..d1227b0cc2 100644
--- a/Pinta.Tools/Editable/EditEngines/BaseEditEngine.cs
+++ b/Pinta.Tools/Editable/EditEngines/BaseEditEngine.cs
@@ -296,8 +296,12 @@ public void HandleBuildToolBar (Gtk.Box tb, ISettingsService settings, string to
 				//if shape is selected it will be converted to new shape and shape type will be changed, otherwise only shape type will be changed.
 
 				//Create a new ShapesModifyHistoryItem so that the changing of the shape type can be undone.
-				workspace.ActiveDocument.History.PushNewItem (new ShapesModifyHistoryItem (
-					this, owner.Icon, Translations.GetString ("Changed Shape Type")));
+				workspace.ActiveDocument.History.PushNewItem (
+					new ShapesModifyHistoryItem (
+						this,
+						owner.Icon,
+						Translations.GetString ("Changed Shape Type")),
+					actions.Edit);
 
 				//Clone the old shape; it should be automatically garbage-collected. newShapeType already has the updated value.
 				selEngine = selEngine.Convert (newShapeType, SelectedShapeIndex);
@@ -617,8 +621,8 @@ private void HandleSpace (ToolKeyEventArgs e)
 			new ShapesModifyHistoryItem (
 				this,
 				owner.Icon,
-				ShapeName + " " + Translations.GetString ("Point Added")
-			)
+				ShapeName + " " + Translations.GetString ("Point Added")),
+			actions.Edit
 		);
 
 		bool shiftKey = e.IsShiftPressed;
@@ -668,8 +672,8 @@ private void HandleDelete ()
 				new ShapesModifyHistoryItem (
 					this,
 					owner.Icon,
-					ShapeName + " " + Translations.GetString ("Point Deleted")
-				)
+					ShapeName + " " + Translations.GetString ("Point Deleted")),
+				actions.Edit
 			);
 
 			//Delete the selected point from the shape.
@@ -692,8 +696,8 @@ private void HandleDelete ()
 					doc.Layers.CurrentUserLayer,
 					SelectedPointIndex,
 					SelectedShapeIndex,
-					false
-				)
+					false),
+				actions.Edit
 			);
 
 
@@ -820,7 +824,13 @@ public virtual void HandleMouseDown (Document document, ToolMouseEventArgs e)
 			//Only create a new shape if the user isn't holding the control key down.
 			if (!ctrlKey) {
 				//Create a new ShapesModifyHistoryItem so that the adding of a control point can be undone.
-				doc.History.PushNewItem (new ShapesModifyHistoryItem (this, owner.Icon, ShapeName + " " + Translations.GetString ("Point Added")));
+				doc.History.PushNewItem (
+					new ShapesModifyHistoryItem (
+						this,
+						owner.Icon,
+						ShapeName + " " + Translations.GetString ("Point Added")),
+					actions.Edit
+				);
 
 				SEngines[closestShapeIndex].ControlPoints.Insert (closestPointIndex,
 					new ControlPoint (new PointD (current_point.X, current_point.Y), DefaultMidPointTension));
@@ -849,8 +859,17 @@ public virtual void HandleMouseDown (Document document, ToolMouseEventArgs e)
 			}
 
 			//Create a new ShapesHistoryItem so that the creation of a new shape can be undone.
-			doc.History.PushNewItem (new ShapesHistoryItem (this, owner.Icon, ShapeName + " " + Translations.GetString ("Added"),
-				doc.Layers.CurrentUserLayer.Surface.Clone (), doc.Layers.CurrentUserLayer, SelectedPointIndex, SelectedShapeIndex, false));
+			doc.History.PushNewItem (
+				new ShapesHistoryItem (
+					this,
+					owner.Icon,
+					ShapeName + " " + Translations.GetString ("Added"),
+					doc.Layers.CurrentUserLayer.Surface.Clone (),
+					doc.Layers.CurrentUserLayer,
+					SelectedPointIndex,
+					SelectedShapeIndex,
+					false),
+				actions.Edit);
 
 			//Create the shape, add its starting points, and add it to SEngines.
 			SEngines.Add (CreateShape (ctrlKey, clicked_control_point, prevSelPoint));
@@ -929,9 +948,15 @@ public virtual void HandleMouseMove (Document document, ToolMouseEventArgs e)
 		}
 
 		if (clicked_without_modifying) {
-			//Create a new ShapesModifyHistoryItem so that the modification of the shape can be undone.
+
+			// Create a new ShapesModifyHistoryItem so that the modification of the shape can be undone.
 			doc.History.PushNewItem (
-							new ShapesModifyHistoryItem (this, owner.Icon, ShapeName + " " + Translations.GetString ("Modified")));
+				new ShapesModifyHistoryItem (
+					this,
+					owner.Icon,
+					ShapeName + " " + Translations.GetString ("Modified")),
+				actions.Edit
+			);
 
 			clicked_without_modifying = false;
 		}
@@ -1119,8 +1144,8 @@ private RectangleD DrawFinalized (ShapeEngine engine, bool createHistoryItem, bo
 					doc.Layers.CurrentUserLayer,
 					SelectedPointIndex,
 					SelectedShapeIndex,
-					false
-				)
+					false),
+				actions.Edit
 			);
 		}
 
@@ -1400,8 +1425,18 @@ protected void FinalizeAllShapes ()
 		//Make sure that the undo surface isn't null.
 		if (undoSurface != null) {
 			//Create a new ShapesHistoryItem so that the finalization of the shapes can be undone.
-			doc.History.PushNewItem (new ShapesHistoryItem (this, owner.Icon, Translations.GetString ("Finalized"),
-				undoSurface, doc.Layers.CurrentUserLayer, previousSelectedPointIndex, prev_selected_shape_index, true));
+			doc.History.PushNewItem (
+				new ShapesHistoryItem (
+					this,
+					owner.Icon,
+					Translations.GetString ("Finalized"),
+					undoSurface,
+					doc.Layers.CurrentUserLayer,
+					previousSelectedPointIndex,
+					prev_selected_shape_index,
+					true),
+				actions.Edit
+			);
 		}
 
 		if (totalDirty.HasValue) {
diff --git a/Pinta.Tools/Tools/BaseBrushTool.cs b/Pinta.Tools/Tools/BaseBrushTool.cs
index 11d98d7336..11219ea19c 100644
--- a/Pinta.Tools/Tools/BaseBrushTool.cs
+++ b/Pinta.Tools/Tools/BaseBrushTool.cs
@@ -85,7 +85,14 @@ protected override void OnMouseDown (Document document, ToolMouseEventArgs e)
 	protected override void OnMouseUp (Document document, ToolMouseEventArgs e)
 	{
 		if (undo_surface != null && surface_modified) {
-			document.History.PushNewItem (new SimpleHistoryItem (Icon, Name, undo_surface, document.Layers.CurrentUserLayerIndex));
+			document.History.PushNewItem (
+				new SimpleHistoryItem (
+					Icon,
+					Name,
+					undo_surface,
+					document.Layers.CurrentUserLayerIndex),
+				PintaCore.Actions.Edit
+			);
 		}
 
 		surface_modified = false;
diff --git a/Pinta.Tools/Tools/FreeformShapeTool.cs b/Pinta.Tools/Tools/FreeformShapeTool.cs
index 7a8902ce24..2a2e48747e 100644
--- a/Pinta.Tools/Tools/FreeformShapeTool.cs
+++ b/Pinta.Tools/Tools/FreeformShapeTool.cs
@@ -189,8 +189,16 @@ protected override void OnMouseUp (Document document, ToolMouseEventArgs e)
 			g.Stroke ();
 		}
 
-		if (surface_modified && undo_surface != null)
-			document.History.PushNewItem (new SimpleHistoryItem (Icon, Name, undo_surface, document.Layers.CurrentUserLayerIndex));
+		if (surface_modified && undo_surface != null) {
+			document.History.PushNewItem (
+				new SimpleHistoryItem (
+					Icon,
+					Name,
+					undo_surface,
+					document.Layers.CurrentUserLayerIndex),
+				PintaCore.Actions.Edit
+			);
+		}
 
 		undo_surface = null;
 		surface_modified = false;
diff --git a/Pinta.Tools/Tools/GradientTool.cs b/Pinta.Tools/Tools/GradientTool.cs
index e64ac1fc74..500e99c5bd 100644
--- a/Pinta.Tools/Tools/GradientTool.cs
+++ b/Pinta.Tools/Tools/GradientTool.cs
@@ -123,11 +123,21 @@ protected override void OnMouseUp (Document document, ToolMouseEventArgs e)
 		document.Layers.ToolLayer.Clear ();
 
 		if (undo_surface != null) {
+
 			string name = is_newly_created
 				? Translations.GetString ("Gradient Created")
 				: Translations.GetString ("Gradient Modified");
-			document.History.PushNewItem (new GradientHistoryItem (Icon, name, undo_surface,
-				document.Layers.CurrentUserLayerIndex, undo_data!.Value, this));
+
+			document.History.PushNewItem (
+				new GradientHistoryItem (
+					Icon,
+					name,
+					undo_surface,
+					document.Layers.CurrentUserLayerIndex,
+					undo_data!.Value,
+					this),
+				PintaCore.Actions.Edit
+			);
 		}
 
 		is_newly_created = false;
@@ -183,8 +193,16 @@ private void Finalize (Document? document)
 		if (document != null) {
 			undo_data = Data;
 			undo_surface = document.Layers.CurrentUserLayer.Surface.Clone ();
-			document.History.PushNewItem (new GradientHistoryItem (Icon, Name + " " + Translations.GetString ("Finalized"), undo_surface,
-						document.Layers.CurrentUserLayerIndex, undo_data!.Value, this));
+			document.History.PushNewItem (
+				new GradientHistoryItem (
+					Icon,
+					Name + " " + Translations.GetString ("Finalized"),
+					undo_surface,
+					document.Layers.CurrentUserLayerIndex,
+					undo_data!.Value,
+					this),
+				PintaCore.Actions.Edit
+			);
 		}
 		handle.Active = false;
 
diff --git a/Pinta.Tools/Tools/LassoSelectTool.cs b/Pinta.Tools/Tools/LassoSelectTool.cs
index 4392d1d64c..e8d9a2a3fb 100644
--- a/Pinta.Tools/Tools/LassoSelectTool.cs
+++ b/Pinta.Tools/Tools/LassoSelectTool.cs
@@ -149,7 +149,7 @@ private void FinalizeShape (Document document)
 	{
 		if (hist != null) {
 			if (lasso_polygon.Count > 1)
-				document.History.PushNewItem (hist);
+				document.History.PushNewItem (hist, PintaCore.Actions.Edit);
 			hist = null;
 		}
 		lasso_polygon.Clear ();
diff --git a/Pinta.Tools/Tools/MagicWandTool.cs b/Pinta.Tools/Tools/MagicWandTool.cs
index 039c37b1f9..021e298166 100644
--- a/Pinta.Tools/Tools/MagicWandTool.cs
+++ b/Pinta.Tools/Tools/MagicWandTool.cs
@@ -90,7 +90,7 @@ protected override void OnFillRegionComputed (Document document, IReadOnlyList<I
 		document.Selection.SelectionPolygons.Clear ();
 		SelectionModeHandler.PerformSelectionMode (document, combine_mode, DocumentSelection.ConvertToPolygons (polygonSet));
 
-		document.History.PushNewItem (undoAction);
+		document.History.PushNewItem (undoAction, PintaCore.Actions.Edit);
 	}
 
 	protected override void OnSaveSettings (ISettingsService settings)
diff --git a/Pinta.Tools/Tools/MoveSelectedTool.cs b/Pinta.Tools/Tools/MoveSelectedTool.cs
index 65a6f7e930..f33b438fc1 100644
--- a/Pinta.Tools/Tools/MoveSelectedTool.cs
+++ b/Pinta.Tools/Tools/MoveSelectedTool.cs
@@ -126,7 +126,7 @@ protected override void OnFinishTransform (Document document, Matrix transform)
 		document.PreviousSelection = prev_selection.Transform (transform);
 
 		if (hist != null)
-			document.History.PushNewItem (hist);
+			document.History.PushNewItem (hist, PintaCore.Actions.Edit);
 
 		hist = null;
 		original_selection = null;
diff --git a/Pinta.Tools/Tools/MoveSelectionTool.cs b/Pinta.Tools/Tools/MoveSelectionTool.cs
index 8c617d9554..bfb28c6a1c 100644
--- a/Pinta.Tools/Tools/MoveSelectionTool.cs
+++ b/Pinta.Tools/Tools/MoveSelectionTool.cs
@@ -93,7 +93,7 @@ protected override void OnFinishTransform (Document document, Matrix transform)
 		document.PreviousSelection = prev_selection.Transform (transform);
 
 		if (hist != null)
-			document.History.PushNewItem (hist);
+			document.History.PushNewItem (hist, PintaCore.Actions.Edit);
 
 		hist = null;
 
diff --git a/Pinta.Tools/Tools/PaintBucketTool.cs b/Pinta.Tools/Tools/PaintBucketTool.cs
index 5df0f3453e..8c44a685c2 100644
--- a/Pinta.Tools/Tools/PaintBucketTool.cs
+++ b/Pinta.Tools/Tools/PaintBucketTool.cs
@@ -100,7 +100,7 @@ protected override void OnFillRegionComputed (Document document, BitMask stencil
 		layer_ctx.Paint ();
 
 		document.Layers.ToolLayer.Clear ();
-		document.History.PushNewItem (hist);
+		document.History.PushNewItem (hist, PintaCore.Actions.Edit);
 		document.Workspace.Invalidate ();
 	}
 }
diff --git a/Pinta.Tools/Tools/PencilTool.cs b/Pinta.Tools/Tools/PencilTool.cs
index 128a024861..3b2ae7d008 100644
--- a/Pinta.Tools/Tools/PencilTool.cs
+++ b/Pinta.Tools/Tools/PencilTool.cs
@@ -103,8 +103,16 @@ protected override void OnMouseMove (Document document, ToolMouseEventArgs e)
 
 	protected override void OnMouseUp (Document document, ToolMouseEventArgs e)
 	{
-		if (undo_surface != null && surface_modified)
-			document.History.PushNewItem (new SimpleHistoryItem (Icon, Name, undo_surface, document.Layers.CurrentUserLayerIndex));
+		if (undo_surface != null && surface_modified) {
+			document.History.PushNewItem (
+				new SimpleHistoryItem (
+					Icon,
+					Name,
+					undo_surface,
+					document.Layers.CurrentUserLayerIndex),
+				PintaCore.Actions.Edit
+			);
+		}
 
 		surface_modified = false;
 		undo_surface = null;
diff --git a/Pinta.Tools/Tools/SelectTool.cs b/Pinta.Tools/Tools/SelectTool.cs
index 577121d9f8..95dd259171 100644
--- a/Pinta.Tools/Tools/SelectTool.cs
+++ b/Pinta.Tools/Tools/SelectTool.cs
@@ -113,7 +113,7 @@ protected override void OnMouseUp (Document document, ToolMouseEventArgs e)
 			document.Selection.HandleBounds = handle.Rectangle;
 
 			if (hist != null) {
-				document.History.PushNewItem (hist);
+				document.History.PushNewItem (hist, PintaCore.Actions.Edit);
 				hist = null;
 			}
 
diff --git a/Pinta.Tools/Tools/TextTool.cs b/Pinta.Tools/Tools/TextTool.cs
index 7771d447e5..dde52d7b13 100644
--- a/Pinta.Tools/Tools/TextTool.cs
+++ b/Pinta.Tools/Tools/TextTool.cs
@@ -973,7 +973,7 @@ protected override bool OnKeyDown (Document document, ToolKeyEventArgs e)
 								OnHandleUndo (document);
 
 								if (workspace.ActiveDocument.History.CanUndo)
-									workspace.ActiveDocument.History.Undo ();
+									workspace.ActiveDocument.History.Undo (PintaCore.Actions.Edit);
 
 								return true;
 							} else if (e.Key.Value == Gdk.Constants.KEY_i) {
@@ -1150,8 +1150,8 @@ private void StopEditing (bool finalize)
 					text_undo_surface.Clone (),
 					user_undo_surface.Clone (),
 					undo_engine!.Clone (), // NRT - Set in StartEditing
-					doc.Layers.CurrentUserLayer
-				)
+					doc.Layers.CurrentUserLayer),
+				PintaCore.Actions.Edit
 			);
 
 			//Stop ignoring any Surface.Clone calls from this point on.
@@ -1369,7 +1369,7 @@ public void FinalizeText ()
 			doc.Layers.CurrentUserLayer);
 
 		//Add the new TextHistoryItem.
-		doc.History.PushNewItem (hist);
+		doc.History.PushNewItem (hist, PintaCore.Actions.Edit);
 
 		//Stop ignoring any Surface.Clone calls from this point on.
 		ignore_clone_finalizations = false;
diff --git a/Pinta/Actions/Edit/OffsetSelectionAction.cs b/Pinta/Actions/Edit/OffsetSelectionAction.cs
index b25edad452..b11d5ad757 100755
--- a/Pinta/Actions/Edit/OffsetSelectionAction.cs
+++ b/Pinta/Actions/Edit/OffsetSelectionAction.cs
@@ -81,7 +81,7 @@ private async void Activated (object sender, EventArgs e)
 		historyItem.TakeSnapshot ();
 
 		document.Selection.Offset (newOffset);
-		document.History.PushNewItem (historyItem);
+		document.History.PushNewItem (historyItem, edit);
 		document.Workspace.Invalidate ();
 	}
 
diff --git a/Pinta/Actions/Edit/PasteAction.cs b/Pinta/Actions/Edit/PasteAction.cs
index 760537a1e8..5b32be5e5c 100644
--- a/Pinta/Actions/Edit/PasteAction.cs
+++ b/Pinta/Actions/Edit/PasteAction.cs
@@ -199,7 +199,7 @@ public static async void Paste (
 		doc.Workspace.Invalidate ();
 
 		paste_action.Push (new PasteHistoryItem (cb_image, old_selection));
-		doc.History.PushNewItem (paste_action);
+		doc.History.PushNewItem (paste_action, actions.Edit);
 	}
 
 	public static Task ShowClipboardEmptyDialog (ChromeManager chrome)
diff --git a/Pinta/Actions/Layers/LayerPropertiesAction.cs b/Pinta/Actions/Layers/LayerPropertiesAction.cs
index 776aeaa084..8748f38a65 100644
--- a/Pinta/Actions/Layers/LayerPropertiesAction.cs
+++ b/Pinta/Actions/Layers/LayerPropertiesAction.cs
@@ -67,7 +67,7 @@ private async void Activated (object sender, EventArgs e)
 					dialog.InitialLayerProperties,
 					dialog.UpdatedLayerProperties);
 
-				active.History.PushNewItem (historyItem);
+				active.History.PushNewItem (historyItem, PintaCore.Actions.Edit);
 
 				workspace.ActiveWorkspace.Invalidate ();
 			} else {
diff --git a/Pinta/Actions/Layers/RotateZoomLayerAction.cs b/Pinta/Actions/Layers/RotateZoomLayerAction.cs
index bc5162a95c..88a498584a 100644
--- a/Pinta/Actions/Layers/RotateZoomLayerAction.cs
+++ b/Pinta/Actions/Layers/RotateZoomLayerAction.cs
@@ -135,8 +135,8 @@ private void ApplyTransform (RotateZoomData data)
 				Resources.Icons.LayerRotateZoom,
 				Translations.GetString ("Rotate / Zoom Layer"),
 				old_surf,
-				doc.Layers.CurrentUserLayerIndex
-			)
+				doc.Layers.CurrentUserLayerIndex),
+			PintaCore.Actions.Edit
 		);
 	}
 
diff --git a/Pinta/Pads/HistoryPad.cs b/Pinta/Pads/HistoryPad.cs
index 2f613382a8..4b01570450 100644
--- a/Pinta/Pads/HistoryPad.cs
+++ b/Pinta/Pads/HistoryPad.cs
@@ -40,7 +40,7 @@ internal HistoryPad (EditActions edit)
 
 	public void Initialize (Dock workspace)
 	{
-		HistoryListView history = new ();
+		HistoryListView history = new (edit);
 
 		DockItem history_item = new (
 			child: history,