diff --git a/Pinta.Core/Classes/Document.cs b/Pinta.Core/Classes/Document.cs
index c2143a62b8..e0a449b1bb 100644
--- a/Pinta.Core/Classes/Document.cs
+++ b/Pinta.Core/Classes/Document.cs
@@ -25,6 +25,7 @@
 // THE SOFTWARE.
 
 using System;
+using System.Diagnostics.CodeAnalysis;
 using System.Threading.Tasks;
 using Cairo;
 
@@ -140,6 +141,7 @@ public Gio.File? File {
 	/// <summary>
 	/// Whether the document is associated with a file on disk.
 	/// </summary>
+	[MemberNotNullWhen(true, nameof(File))]
 	public bool HasFile => file is not null;
 
 	/// Whether or not the document has been saved to the file that it is currently associated with in the
@@ -445,4 +447,15 @@ private void OnSelectionChanged ()
 	public event EventHandler? Renamed;
 	public event LayerCloneEvent? LayerCloned;
 	public event EventHandler? SelectionChanged;
+
+	private bool is_autosave_dirty;
+	public bool IsAutosaveDirty {
+		get => is_autosave_dirty;
+		set => is_autosave_dirty = value;
+	}
+	private uint autosave_files_index;
+	public uint AutosaveFilesIndex {
+		get => autosave_files_index;
+		set => autosave_files_index = value;
+	}
 }
diff --git a/Pinta.Core/Classes/DocumentHistory.cs b/Pinta.Core/Classes/DocumentHistory.cs
index 5a25ed7047..7a8d546408 100644
--- a/Pinta.Core/Classes/DocumentHistory.cs
+++ b/Pinta.Core/Classes/DocumentHistory.cs
@@ -73,8 +73,10 @@ public void PushNewItem (BaseHistoryItem newItem)
 		history.Add (newItem);
 		Pointer = history.Count - 1;
 
-		if (newItem.CausesDirty)
+		if (newItem.CausesDirty) {
 			document.IsDirty = true;
+			document.IsAutosaveDirty = true;
+		}
 
 		HistoryItemAdded?.Invoke (this, new HistoryItemAddedEventArgs (newItem));
 	}
diff --git a/Pinta.Core/Managers/WorkspaceManager.cs b/Pinta.Core/Managers/WorkspaceManager.cs
index 97e0b03328..8ae3f52ed1 100644
--- a/Pinta.Core/Managers/WorkspaceManager.cs
+++ b/Pinta.Core/Managers/WorkspaceManager.cs
@@ -161,7 +161,8 @@ public sealed class WorkspaceManager : IWorkspaceService
 	public WorkspaceManager (
 		SystemManager systemManager,
 		ChromeManager chromeManager,
-		ImageConverterManager imageFormats)
+		ImageConverterManager imageFormats,
+		SettingsManager settings)
 	{
 		open_documents = [];
 		OpenDocuments = new ReadOnlyCollection<Document> (open_documents);
@@ -169,6 +170,8 @@ public WorkspaceManager (
 
 		chrome_manager = chromeManager;
 		image_formats = imageFormats;
+
+		StartAutosaveTimer(settings);
 	}
 
 	public int ActiveDocumentIndex
@@ -465,6 +468,89 @@ private Task ShowFilePermissionErrorDialog (
 		return chrome_manager.ShowMessageDialog (parent, message, details);
 	}
 
+	private uint autosave_timer_id;
+	private uint autosave_files;
+	private int autosave_history;
+	private readonly HashSet<string> autosaveFiles = new();
+	private void StartAutosaveTimer (SettingsManager settings)
+	{
+		int interval = settings.GetSetting("autosave-interval", 0);
+		if (interval > 0) {
+			autosave_files = Math.Max(1, (uint)settings.GetSetting("autosave-files", 1));
+			autosave_history = settings.GetSetting("autosave-history", 0);
+			autosave_timer_id = GLib.Functions.TimeoutAdd(GLib.Constants.PRIORITY_DEFAULT, (uint)interval * 1000, OnAutosaveTick);
+		}
+	}
+	private bool OnAutosaveTick ()
+	{
+		if (!HasOpenDocuments)
+			return true;
+
+		var format = PintaCore.ImageFormats.GetFormatByExtension ("ora");
+		if (format?.Exporter is null) {
+			autosave_timer_id = 0;
+			return false;
+		}
+
+		foreach (var doc in OpenDocuments) {
+			if (!doc.HasFile)
+				continue;
+			if (!doc.IsAutosaveDirty)
+				continue;
+
+			string autosaveFile = doc.File.GetParseName() + ".pinta_autosave_" + doc.AutosaveFilesIndex + ".ora";
+			doc.AutosaveFilesIndex += 1;
+			if ( doc.AutosaveFilesIndex == autosave_files ) doc.AutosaveFilesIndex = 0;
+
+			format.Exporter.Export (doc, Gio.FileHelper.NewForPath (autosaveFile), PintaCore.Chrome.MainWindow);
+
+			autosaveFiles.Add(autosaveFile);
+			DumpLastHistorySteps(doc);
+			doc.IsAutosaveDirty = false;
+		}
+		if ( autosave_history != 0 ) {
+			Console.WriteLine($"Date: {DateTime.Now:yyyy-MM-dd HH:mm:ss}");
+		}
+
+		return true;
+	}
+	public void StopAutosave () {
+		if (autosave_timer_id != 0)
+		{
+			GLib.Source.Remove(autosave_timer_id);
+		}
+		foreach (var file_string in autosaveFiles)
+		{
+			try
+			{
+				var file = Gio.FileHelper.NewForPath(file_string);
+				if (file.QueryExists(null))
+					file.Delete(null);
+			}
+			catch
+			{
+				// ignore cleanup failures
+			}
+		}
+		autosaveFiles.Clear();
+	}
+	private void DumpLastHistorySteps(Document doc)
+	{
+		if ( autosave_history != 0 ) {
+			Console.WriteLine("=== Last History Steps ===");
+
+			var history = doc.History;
+			var n = history.Items.Count();
+			for (var i = Math.Max(0, n - autosave_history); i < n; i++)
+			{
+				var item = history.Items.ElementAt(i);
+				Console.WriteLine($"[{i}] {item.Text}");
+			}
+
+			Console.WriteLine("==========================");
+		}
+	}
+
 	public event EventHandler? LayerAdded;
 	public event EventHandler? LayerRemoved;
 	public event EventHandler? SelectedLayerChanged;
diff --git a/Pinta.Core/PintaCore.cs b/Pinta.Core/PintaCore.cs
index abdba7e115..3a85197d36 100644
--- a/Pinta.Core/PintaCore.cs
+++ b/Pinta.Core/PintaCore.cs
@@ -78,7 +78,7 @@ static PintaCore ()
 		// --- Services that depend on other services
 
 		ImageConverterManager imageFormats = new (settings);
-		WorkspaceManager workspace = new (system, chrome, imageFormats);
+		WorkspaceManager workspace = new (system, chrome, imageFormats, settings);
 		ToolManager tools = new (workspace, chrome);
 		PaletteManager palette = new (settings, paletteFormats);
 		ActionManager actions = new (chrome, imageFormats, paletteFormats, palette, recentFiles, system, tools, workspace);
diff --git a/Pinta/Actions/File/ExitAction.cs b/Pinta/Actions/File/ExitAction.cs
index 746c59b7a4..870a0e89d2 100644
--- a/Pinta/Actions/File/ExitAction.cs
+++ b/Pinta/Actions/File/ExitAction.cs
@@ -67,6 +67,8 @@ private void Activated (object sender, EventArgs e)
 				return;
 		}
 
+		PintaCore.Workspace.StopAutosave();
+
 		// Let everyone know we are quitting
 		actions.App.RaiseBeforeQuit ();