diff --git a/Pinta.Core/Actions/EditActions.cs b/Pinta.Core/Actions/EditActions.cs
index c0dc0757cd..45508e7f1e 100644
--- a/Pinta.Core/Actions/EditActions.cs
+++ b/Pinta.Core/Actions/EditActions.cs
@@ -53,6 +53,7 @@ public sealed class EditActions
 	public Command ResizePalette { get; }
 
 	private Gio.File? last_palette_dir = null;
+	private Document? active_document = null;
 
 	private readonly ChromeManager chrome;
 	private readonly PaletteFormatManager palette_formats;
@@ -616,14 +617,41 @@ void HandleInvertSelectionActivated (object sender, EventArgs e)
 
 	private void WorkspaceActiveDocumentChanged (object? sender, EventArgs e)
 	{
-		if (!workspace.HasOpenDocuments) {
-			Undo.Sensitive = false;
+		if (active_document != null) {
+			active_document.History.HistoryItemAdded -= OnDocumentHistoryChanged;
+			active_document.History.ActionRedone -= OnDocumentHistoryChanged;
+			active_document.History.ActionUndone -= OnDocumentHistoryChanged;
+		}
+
+		active_document = workspace.ActiveDocumentOrDefault;
+
+		// Register event handlers for the new document to update the undo/redo state.
+		if (active_document != null) {
+			active_document.History.HistoryItemAdded += OnDocumentHistoryChanged;
+			active_document.History.ActionRedone += OnDocumentHistoryChanged;
+			active_document.History.ActionUndone += OnDocumentHistoryChanged;
+		}
+
+		// Force an update of the undo/redo state after switching documents.
+		UpdateUndoRedoActions ();
+	}
+
+	private void OnDocumentHistoryChanged (object? sender, EventArgs e)
+	{
+		UpdateUndoRedoActions ();
+	}
+
+	private void UpdateUndoRedoActions ()
+	{
+		if (active_document != null) {
+			Redo.Sensitive = active_document.Workspace.History.CanRedo;
+			Undo.Sensitive = active_document.Workspace.History.CanUndo;
+		} else {
 			Redo.Sensitive = false;
-			return;
+			Undo.Sensitive = false;
 		}
 
-		Redo.Sensitive = workspace.ActiveWorkspace.History.CanRedo;
-		Undo.Sensitive = workspace.ActiveWorkspace.History.CanUndo;
 	}
+
 	#endregion
 }
diff --git a/Pinta.Core/Classes/DocumentHistory.cs b/Pinta.Core/Classes/DocumentHistory.cs
index 402babbf50..5a25ed7047 100644
--- a/Pinta.Core/Classes/DocumentHistory.cs
+++ b/Pinta.Core/Classes/DocumentHistory.cs
@@ -1,21 +1,21 @@
-// 
+//
 // DocumentHistory.cs
-//  
+//
 // Author:
 //       Jonathan Pobst <monkey@jpobst.com>
-// 
+//
 // Copyright (c) 2010 Jonathan Pobst
-// 
+//
 // Permission is hereby granted, free of charge, to any person obtaining a copy
 // of this software and associated documentation files (the "Software"), to deal
 // in the Software without restriction, including without limitation the rights
 // to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
 // copies of the Software, and to permit persons to whom the Software is
 // furnished to do so, subject to the following conditions:
-// 
+//
 // The above copyright notice and this permission notice shall be included in
 // all copies or substantial portions of the Software.
-// 
+//
 // THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
 // IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
 // FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
@@ -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;
 	}
 
@@ -81,11 +76,6 @@ public void PushNewItem (BaseHistoryItem newItem)
 		if (newItem.CausesDirty)
 			document.IsDirty = true;
 
-		if (history.Count > 1)
-			edit.Undo.Sensitive = true;
-
-		edit.Redo.Sensitive = false;
-
 		HistoryItemAdded?.Invoke (this, new HistoryItemAddedEventArgs (newItem));
 	}
 
@@ -106,11 +96,6 @@ public void Undo ()
 		if (Pointer == clean_pointer)
 			document.IsDirty = false;
 
-		if (Pointer == 0)
-			edit.Undo.Sensitive = false;
-
-		edit.Redo.Sensitive = true;
-
 		ActionUndone?.Invoke (this, EventArgs.Empty);
 	}
 
@@ -125,17 +110,11 @@ public void Redo ()
 		item.Redo ();
 		item.State = HistoryItemState.Undo;
 
-		if (Pointer == history.Count - 1)
-			edit.Redo.Sensitive = false;
-
 		if (Pointer == clean_pointer)
 			document.IsDirty = false;
 		else if (item.CausesDirty)
 			document.IsDirty = true;
 
-		if (history.Count > 1)
-			edit.Undo.Sensitive = true;
-
 		ActionRedone?.Invoke (this, EventArgs.Empty);
 	}
 
@@ -167,8 +146,5 @@ public void Clear ()
 		clean_pointer = -1;
 
 		document.IsDirty = false;
-
-		edit.Redo.Sensitive = false;
-		edit.Undo.Sensitive = false;
 	}
 }
diff --git a/Pinta.Core/Classes/DocumentWorkspace.cs b/Pinta.Core/Classes/DocumentWorkspace.cs
index b9af931a07..924fb50318 100644
--- a/Pinta.Core/Classes/DocumentWorkspace.cs
+++ b/Pinta.Core/Classes/DocumentWorkspace.cs
@@ -49,7 +49,7 @@ internal DocumentWorkspace (
 
 		this.document = document;
 
-		History = new DocumentHistory (actions.Edit, document);
+		History = new DocumentHistory (document);
 	}
 
 	#region Public Events