diff --git a/mptrack/AutoSaver.cpp b/mptrack/AutoSaver.cpp
index f19c1b669c..4c008ca0c1 100644
--- a/mptrack/AutoSaver.cpp
+++ b/mptrack/AutoSaver.cpp
@@ -28,7 +28,7 @@ OPENMPT_NAMESPACE_BEGIN
 
 
 CAutoSaver::CAutoSaver()
-	: m_lastSave(timeGetTime())
+	: m_lastSave{timeGetTime()}
 {
 }
 
@@ -53,32 +53,38 @@ uint32 CAutoSaver::GetHistoryDepth() const
 	return TrackerSettings::Instance().AutosaveHistoryDepth;
 }
 
-uint32 CAutoSaver::GetSaveInterval() const
+std::chrono::minutes CAutoSaver::GetSaveInterval() const
 {
-	return TrackerSettings::Instance().AutosaveIntervalMinutes;
+	return std::chrono::minutes{TrackerSettings::Instance().AutosaveIntervalMinutes.Get()};
 }
 
 
-bool CAutoSaver::DoSave(DWORD curTime)
+std::chrono::days CAutoSaver::GetRetentionTime() const
+{
+	return std::chrono::days{TrackerSettings::Instance().AutosaveRetentionTimeDays.Get()};
+}
+
+
+bool CAutoSaver::DoSave()
 {
 	// Do nothing if we are already saving, or if time to save has not been reached yet.
-	if(m_saveInProgress || !CheckTimer(curTime))
+	if(m_saveInProgress || !CheckTimer(timeGetTime()))
 		return true;
 		
 	bool success = true, clearStatus = false;
 	m_saveInProgress = true;
 
-	theApp.BeginWaitCursor(); // Display hour glass
+	theApp.BeginWaitCursor();  // Display hour glass
 
 	for(auto &modDoc : theApp.GetOpenDocuments())
 	{
 		if(modDoc->ModifiedSinceLastAutosave())
 		{
 			clearStatus = true;
-			static_cast<CMainFrame *>(theApp.GetMainWnd())->SetHelpText(MPT_CFORMAT("Auto-saving {}...")(modDoc->GetPathNameMpt().GetFilename()));
+			CMainFrame::GetMainFrame()->SetHelpText(MPT_CFORMAT("Auto-saving {}...")(modDoc->GetPathNameMpt().GetFilename()));
 			if(SaveSingleFile(*modDoc))
 			{
-				CleanUpBackups(*modDoc);
+				CleanUpAutosaves(*modDoc);
 			} else
 			{
 				TrackerSettings::Instance().AutosaveEnabled = false;
@@ -87,13 +93,14 @@ bool CAutoSaver::DoSave(DWORD curTime)
 			}
 		}
 	}
+	CleanUpAutosaves();
 
 	m_lastSave = timeGetTime();
 	theApp.EndWaitCursor();  // End display hour glass
 	m_saveInProgress = false;
 
 	if(clearStatus)
-		static_cast<CMainFrame *>(theApp.GetMainWnd())->SetHelpText(_T(""));
+		CMainFrame::GetMainFrame()->SetHelpText(_T(""));
 	
 	return success;
 }
@@ -101,7 +108,7 @@ bool CAutoSaver::DoSave(DWORD curTime)
 
 bool CAutoSaver::CheckTimer(DWORD curTime) const
 {
-	return (curTime - m_lastSave) >= GetSaveIntervalMilliseconds();
+	return std::chrono::milliseconds{curTime - m_lastSave} >= GetSaveInterval();
 }
 
 
@@ -149,41 +156,19 @@ mpt::PathString CAutoSaver::BuildFileName(const CModDoc &modDoc) const
 
 bool CAutoSaver::SaveSingleFile(CModDoc &modDoc)
 {
-	// We do not call CModDoc::DoSave as this populates the Recent Files
-	// list with backups... hence we have duplicated code.. :(
-	CSoundFile &sndFile = modDoc.GetSoundFile();
-	
 	mpt::PathString fileName = BuildFileName(modDoc);
 
 	// We are actually not going to show the log for autosaved files.
 	ScopedLogCapturer logcapturer(modDoc, _T(""), nullptr, false);
-
-	bool success = false;
-	mpt::ofstream f(fileName, std::ios::binary);
-	if(f)
-	{
-		switch(modDoc.GetSoundFile().GetBestSaveFormat())
-		{
-		case MOD_TYPE_MOD: success = sndFile.SaveMod(f); break;
-		case MOD_TYPE_S3M: success = sndFile.SaveS3M(f); break;
-		case MOD_TYPE_XM:  success = sndFile.SaveXM(f); break;
-		case MOD_TYPE_IT:  success = sndFile.SaveIT(f, GetUseOriginalPath() ? fileName : mpt::PathString{}); break;
-		case MOD_TYPE_MPT: success = sndFile.SaveIT(f, GetUseOriginalPath() ? fileName : mpt::PathString{}); break;
-		default:
-			// nothing
-			break;
-		}
-	}
-
-	return success;
+	return modDoc.SaveFile(BuildFileName(modDoc), GetUseOriginalPath());
 }
 
 
-void CAutoSaver::CleanUpBackups(const CModDoc &modDoc) const
+void CAutoSaver::CleanUpAutosaves(const CModDoc &modDoc) const
 {
 	// Find all autosave files for this document, and delete the oldest ones if there are more than the user wants.
 	std::vector<mpt::PathString> foundfiles;
-	FolderScanner scanner(GetBasePath(modDoc, false), FolderScanner::kOnlyFiles, GetBaseName(modDoc) + P_(".AutoSave.*"));
+	FolderScanner scanner(GetBasePath(modDoc, false), FolderScanner::kOnlyFiles, GetBaseName(modDoc) + P_(".AutoSave.*.*.*"));
 	mpt::PathString fileName;
 	while(scanner.Next(fileName))
 	{
@@ -191,11 +176,53 @@ void CAutoSaver::CleanUpBackups(const CModDoc &modDoc) const
 	}
 	std::sort(foundfiles.begin(), foundfiles.end());
 	size_t filesToDelete = std::max(static_cast<size_t>(GetHistoryDepth()), foundfiles.size()) - GetHistoryDepth();
+	const bool deletePermanently = TrackerSettings::Instance().AutosaveDeletePermanently;
 	for(size_t i = 0; i < filesToDelete; i++)
 	{
-		DeleteFile(foundfiles[i].AsNative().c_str());
+		DeleteAutosave(foundfiles[i], deletePermanently);
 	}
 }
 
 
+// Find all autosave files in the autosave folder and delete all of those older than X days
+void CAutoSaver::CleanUpAutosaves() const
+{
+	if(GetUseOriginalPath() || !GetRetentionTime().count())
+		return;
+	auto path = GetPath();
+	if(!mpt::native_fs{}.is_directory(path))
+		return;
+	const std::chrono::seconds maxAge = GetRetentionTime();
+	const bool deletePermanently = TrackerSettings::Instance().AutosaveDeletePermanently;
+	FILETIME sysFileTime;
+	GetSystemTimeAsFileTime(&sysFileTime);
+	const int64 currentTime = static_cast<int64>(mpt::bit_cast<ULARGE_INTEGER>(sysFileTime).QuadPart);
+	FolderScanner scanner(std::move(path), FolderScanner::kOnlyFiles, P_("*.AutoSave.*.*.*"));
+	mpt::PathString fileName;
+	WIN32_FIND_DATA fileInfo;
+	while(scanner.Next(fileName, &fileInfo))
+	{
+		const auto fileTime = static_cast<int64>(mpt::bit_cast<ULARGE_INTEGER>(fileInfo.ftLastWriteTime).QuadPart);
+		const auto timeDiff = std::chrono::seconds{(currentTime - fileTime) / 10000000};
+		if(timeDiff >= maxAge)
+			DeleteAutosave(fileName, deletePermanently);
+	}
+}
+
+
+void CAutoSaver::DeleteAutosave(const mpt::PathString &fileName, bool deletePermanently)
+{
+	// Create double-null-terminated path list
+	// Note: We could supply multiple filenames here. However, if the files in total are too big for the recycling bin,
+	// this will cause all of them to be deleted permanently. If we supply them one by one, at least some of them
+	// will go to the recycling bin until it is full.
+	mpt::winstring path = fileName.AsNative() + _T('\0');
+	SHFILEOPSTRUCT fos{};
+	fos.hwnd = CMainFrame::GetMainFrame()->m_hWnd;
+	fos.wFunc = FO_DELETE;
+	fos.pFrom = path.c_str();
+	fos.fFlags = (deletePermanently ? 0 : FOF_ALLOWUNDO) | FOF_NO_UI;
+	SHFileOperation(&fos);
+}
+
 OPENMPT_NAMESPACE_END
diff --git a/mptrack/AutoSaver.h b/mptrack/AutoSaver.h
index 42f7b74dd5..66d70da331 100644
--- a/mptrack/AutoSaver.h
+++ b/mptrack/AutoSaver.h
@@ -21,28 +21,27 @@ class CAutoSaver
 public:
 	CAutoSaver();
 	
-	bool DoSave(DWORD curTime);
+	bool DoSave();
 
 	bool IsEnabled() const;
 	bool GetUseOriginalPath() const;
 	mpt::PathString GetPath() const;
 	uint32 GetHistoryDepth() const;
-	uint32 GetSaveInterval() const;
-	uint32 GetSaveIntervalMilliseconds() const
-	{
-		return Clamp(GetSaveInterval(), 0u, (1u << 30) / 60u / 1000u) * 60 * 1000;
-	}
+	std::chrono::minutes GetSaveInterval() const;
+	std::chrono::days GetRetentionTime() const;
 
 private:
 	bool SaveSingleFile(CModDoc &modDoc);
 	mpt::PathString GetBasePath(const CModDoc &modDoc, bool createPath) const;
 	mpt::PathString GetBaseName(const CModDoc &modDoc) const;
 	mpt::PathString BuildFileName(const CModDoc &modDoc) const;
-	void CleanUpBackups(const CModDoc &modDoc) const;
+	void CleanUpAutosaves(const CModDoc &modDoc) const;
+	void CleanUpAutosaves() const;
 	bool CheckTimer(DWORD curTime) const;
+	static void DeleteAutosave(const mpt::PathString &fileName, bool deletePermanently);
 	
 	DWORD m_lastSave = 0;
-	//Flag to prevent autosave from starting new saving if previous is still in progress.
+	// Flag to prevent autosave from starting new saving if previous is still in progress.
 	bool m_saveInProgress = false;
 
 };
diff --git a/mptrack/FolderScanner.cpp b/mptrack/FolderScanner.cpp
index 7ed7c7e7eb..bdbb50ae20 100644
--- a/mptrack/FolderScanner.cpp
+++ b/mptrack/FolderScanner.cpp
@@ -14,19 +14,18 @@
 
 OPENMPT_NAMESPACE_BEGIN
 
-FolderScanner::FolderScanner(const mpt::PathString &path, FlagSet<ScanType> type, mpt::PathString filter)
-	: m_paths(1, path)
-	, m_filter(std::move(filter))
-	, m_hFind(INVALID_HANDLE_VALUE)
-	, m_type(type)
+FolderScanner::FolderScanner(mpt::PathString path, FlagSet<ScanType> type, mpt::PathString filter)
+	: m_paths{1, std::move(path)}
+	, m_filter{std::move(filter)}
+	, m_type{type}
 {
-	MemsetZero(m_wfd);
 }
 
 
 FolderScanner::~FolderScanner()
 {
-	FindClose(m_hFind);
+	if(m_hFind != INVALID_HANDLE_VALUE)
+		FindClose(m_hFind);
 }
 
 #if MPT_COMPILER_MSVC
@@ -34,7 +33,7 @@ FolderScanner::~FolderScanner()
 #pragma warning(push)
 #pragma warning(disable:6387) // 'HANDLE' could be '0'
 #endif // MPT_COMPILER_MSVC
-bool FolderScanner::Next(mpt::PathString &file)
+bool FolderScanner::Next(mpt::PathString &file, WIN32_FIND_DATA *fileInfo)
 {
 	bool found = false;
 	do
@@ -42,13 +41,10 @@ bool FolderScanner::Next(mpt::PathString &file)
 		if(m_hFind == INVALID_HANDLE_VALUE)
 		{
 			if(m_paths.empty())
-			{
 				return false;
-			}
 
-			m_currentPath = m_paths.back();
+			m_currentPath = m_paths.back().WithTrailingSlash();
 			m_paths.pop_back();
-			m_currentPath = m_currentPath.WithTrailingSlash();
 			m_hFind = FindFirstFile(mpt::support_long_path((m_currentPath + m_filter).AsNative()).c_str(), &m_wfd);
 		}
 
@@ -62,29 +58,25 @@ bool FolderScanner::Next(mpt::PathString &file)
 				{
 					if(_tcscmp(m_wfd.cFileName, _T("..")) && _tcscmp(m_wfd.cFileName, _T(".")))
 					{
+						// Add sub directory
 						if(m_type[kFindInSubDirectories])
-						{
-							// Add sub directory
 							m_paths.push_back(file);
-						}
 						if(m_type[kOnlyDirectories])
-						{
 							found = true;
-						}
 					}
 				} else if(m_type[kOnlyFiles])
 				{
 					found = true;
 				}
+				if(found && fileInfo)
+					*fileInfo = m_wfd;
 			} while((nextFile = FindNextFile(m_hFind, &m_wfd)) != FALSE && !found);
 		}
 		if(nextFile == FALSE)
 		{
 			// Done with this directory, advance to next
 			if(m_hFind != INVALID_HANDLE_VALUE)
-			{
 				FindClose(m_hFind);
-			}
 			m_hFind = INVALID_HANDLE_VALUE;
 		}
 	} while(!found);
diff --git a/mptrack/FolderScanner.h b/mptrack/FolderScanner.h
index c55fcbfa80..292f7c7ba0 100644
--- a/mptrack/FolderScanner.h
+++ b/mptrack/FolderScanner.h
@@ -27,20 +27,19 @@ class FolderScanner
 		kFindInSubDirectories = 0x04,
 	};
 
-protected:
-	std::vector<mpt::PathString> m_paths;
-	mpt::PathString m_currentPath;
-	mpt::PathString m_filter;
-	HANDLE m_hFind;
-	WIN32_FIND_DATA m_wfd;
-	FlagSet<ScanType> m_type;
-
-public:
-	FolderScanner(const mpt::PathString &path, FlagSet<ScanType> type, mpt::PathString filter = MPT_PATHSTRING("*.*"));
+	FolderScanner(mpt::PathString path, FlagSet<ScanType> type, mpt::PathString filter = P_("*.*"));
 	~FolderScanner();
 
 	// Return one file or directory at a time in parameter file. Returns true if a file was found (file parameter is valid), false if no more files can be found (file parameter is not touched).
-	bool Next(mpt::PathString &file);
+	bool Next(mpt::PathString &file, WIN32_FIND_DATA *fileInfo = nullptr);
+
+protected:
+	std::vector<mpt::PathString> m_paths;
+	mpt::PathString m_currentPath;
+	const mpt::PathString m_filter;
+	HANDLE m_hFind = INVALID_HANDLE_VALUE;
+	WIN32_FIND_DATA m_wfd{};
+	const FlagSet<ScanType> m_type;
 };
 
 MPT_DECLARE_ENUM(FolderScanner::ScanType)
diff --git a/mptrack/MainFrm.cpp b/mptrack/MainFrm.cpp
index d235071ba8..516d52ca4f 100644
--- a/mptrack/MainFrm.cpp
+++ b/mptrack/MainFrm.cpp
@@ -2216,17 +2216,14 @@ void CMainFrame::OnTimerGUI()
 		{
 			m_dwTimeSec = time;
 			m_nAvgMixChn = m_nMixChn;
-			OnUpdateTime(NULL);
+			OnUpdateTime(nullptr);
 		}
 	}
 
-	// Idle Time Check
-	DWORD curTime = timeGetTime();
-
 	if(m_AutoSaver.IsEnabled())
 	{
-		bool success = m_AutoSaver.DoSave(curTime);
-		if (!success)		// autosave failure; bring up options.
+		bool success = m_AutoSaver.DoSave();
+		if(!success)  // autosave failure; bring up options.
 		{
 			CMainFrame::m_nLastOptionsPage = OPTIONS_PAGE_PATHS;
 			OnViewOptions();
diff --git a/mptrack/Moddoc.cpp b/mptrack/Moddoc.cpp
index 50cf9f2e66..d1012017cd 100644
--- a/mptrack/Moddoc.cpp
+++ b/mptrack/Moddoc.cpp
@@ -318,65 +318,41 @@ bool CModDoc::OnSaveDocument(const mpt::PathString &filename, const bool setPath
 	if(filename.empty())
 		return false;
 
-	bool ok = false;
 	BeginWaitCursor();
-	m_SndFile.m_dwLastSavedWithVersion = Version::Current();
-	try
+	const bool ok = SaveFile(filename, true);
+	if(ok && m_SndFile.m_SongFlags[SONG_IMPORTED])
 	{
-		mpt::IO::SafeOutputFile sf(filename, std::ios::binary, mpt::IO::FlushModeFromBool(TrackerSettings::Instance().MiscFlushFileBuffersOnSave));
-		mpt::IO::ofstream &f = sf;
-		if(f)
+		const auto formatName = m_SndFile.GetModSpecifications().GetFileExtensionUpper();
+		if(!(GetModType() & (MOD_TYPE_MOD | MOD_TYPE_S3M)))
 		{
-			if(m_SndFile.m_SongFlags[SONG_IMPORTED])
+			// Check if any non-supported playback behaviours are enabled due to being imported from a different format
+			// File saving code will omit those flags automatically, so it's okay if we check and reset them after a successful save only
+			const auto supportedBehaviours = m_SndFile.GetSupportedPlaybackBehaviour(GetModType());
+			bool showWarning = true;
+			for(size_t i = 0; i < kMaxPlayBehaviours; i++)
 			{
-				const auto formatName = m_SndFile.GetModSpecifications().GetFileExtensionUpper();
-				if(!(GetModType() & (MOD_TYPE_MOD | MOD_TYPE_S3M)))
+				if(m_SndFile.m_playBehaviour[i] && !supportedBehaviours[i])
 				{
-					// Check if any non-supported playback behaviours are enabled due to being imported from a different format
-					const auto supportedBehaviours = m_SndFile.GetSupportedPlaybackBehaviour(GetModType());
-					bool showWarning = true;
-					for(size_t i = 0; i < kMaxPlayBehaviours; i++)
+					if(showWarning)
 					{
-						if(m_SndFile.m_playBehaviour[i] && !supportedBehaviours[i])
-						{
-							if(showWarning)
-							{
-								AddToLog(LogWarning, MPT_UFORMAT("Some imported Compatibility Settings that are not supported by the {} format have been disabled. Verify that the module still sounds as intended.")
-									(formatName));
-								showWarning = false;
-							}
-							m_SndFile.m_playBehaviour.reset(i);
-						}
+						AddToLog(LogWarning, MPT_UFORMAT("Some imported Compatibility Settings that are not supported by the {} format have been disabled. Verify that the module still sounds as intended.")(formatName));
+						showWarning = false;
 					}
+					m_SndFile.m_playBehaviour.reset(i);
 				}
-
-				for(INSTRUMENTINDEX i = 1; i <= GetNumInstruments(); i++)
-				{
-					if(m_SndFile.Instruments[i] && m_SndFile.Instruments[i]->synth.HasScripts())
-					{
-						AddToLog(LogWarning, MPT_UFORMAT("Scripted instruments are not supported by the {} format and will not be exported.")(formatName));
-						break;
-					}
-				}
-				if(!m_SndFile.m_globalScript.empty())
-					AddToLog(LogWarning, MPT_UFORMAT("Global instrument scripts are not supported by the {} format and will not be exported.")(formatName));
 			}
+		}
 
-			f.exceptions(f.exceptions() | std::ios::badbit | std::ios::failbit);
-			FixNullStrings();
-			switch(m_SndFile.GetType())
+		for(INSTRUMENTINDEX i = 1; i <= GetNumInstruments(); i++)
+		{
+			if(m_SndFile.Instruments[i] && m_SndFile.Instruments[i]->synth.HasScripts())
 			{
-			case MOD_TYPE_MOD: ok = m_SndFile.SaveMod(f); break;
-			case MOD_TYPE_S3M: ok = m_SndFile.SaveS3M(f); break;
-			case MOD_TYPE_XM:  ok = m_SndFile.SaveXM(f); break;
-			case MOD_TYPE_IT:  ok = m_SndFile.SaveIT(f, filename); break;
-			case MOD_TYPE_MPT: ok = m_SndFile.SaveIT(f, filename); break;
-			default:           MPT_ASSERT_NOTREACHED();
+				AddToLog(LogWarning, MPT_UFORMAT("Scripted instruments are not supported by the {} format and will not be exported.")(formatName));
+				break;
 			}
 		}
-	} catch(const std::exception &)
-	{
-		ok = false;
+		if(!m_SndFile.m_globalScript.empty())
+			AddToLog(LogWarning, MPT_UFORMAT("Global instrument scripts are not supported by the {} format and will not be exported.")(formatName));
 	}
 	EndWaitCursor();
 
@@ -398,6 +374,33 @@ bool CModDoc::OnSaveDocument(const mpt::PathString &filename, const bool setPath
 }
 
 
+bool CModDoc::SaveFile(const mpt::PathString &filename, bool allowRelativeSamplePaths)
+{
+	try
+	{
+		mpt::IO::SafeOutputFile sf(filename, std::ios::binary, mpt::IO::FlushModeFromBool(TrackerSettings::Instance().MiscFlushFileBuffersOnSave));
+		mpt::IO::ofstream &f = sf;
+		if(!f)
+			return false;
+
+		f.exceptions(f.exceptions() | std::ios::badbit | std::ios::failbit);
+		FixNullStrings();
+		switch(m_SndFile.GetBestSaveFormat())
+		{
+		case MOD_TYPE_MOD: return m_SndFile.SaveMod(f);
+		case MOD_TYPE_S3M: return m_SndFile.SaveS3M(f);
+		case MOD_TYPE_XM:  return m_SndFile.SaveXM(f);
+		case MOD_TYPE_IT:  return m_SndFile.SaveIT(f, allowRelativeSamplePaths ? filename : mpt::PathString{});
+		case MOD_TYPE_MPT: return m_SndFile.SaveIT(f, allowRelativeSamplePaths ? filename : mpt::PathString{});
+		default: MPT_ASSERT_NOTREACHED();
+		}
+	} catch(const std::exception &)
+	{
+	}
+	return false;
+}
+
+
 BOOL CModDoc::SaveModified()
 {
 	if(m_SndFile.GetType() == MOD_TYPE_MPT && !SaveAllSamples())
diff --git a/mptrack/Moddoc.h b/mptrack/Moddoc.h
index 7429d8c867..c7db5aa2ff 100644
--- a/mptrack/Moddoc.h
+++ b/mptrack/Moddoc.h
@@ -369,6 +369,7 @@ class CModDoc final : public CDocument
 	void OnCloseDocument() override;
 	void SafeFileClose();
 	bool OnSaveDocument(const mpt::PathString &filename, const bool setPath = true);
+	bool SaveFile(const mpt::PathString &filename, bool allowRelativeSamplePaths);
 
 #if MPT_COMPILER_CLANG
 #pragma clang diagnostic push
diff --git a/mptrack/PathConfigDlg.cpp b/mptrack/PathConfigDlg.cpp
index 5029243e33..2ee24e275a 100644
--- a/mptrack/PathConfigDlg.cpp
+++ b/mptrack/PathConfigDlg.cpp
@@ -74,14 +74,17 @@ BEGIN_MESSAGE_MAP(PathConfigDlg, CPropertyPage)
 	ON_COMMAND(IDC_BUTTON_CHANGE_VSTPRESETSDIR, &PathConfigDlg::OnBrowsePresets)
 
 	// Autosave
-	ON_COMMAND(IDC_CHECK1,						&PathConfigDlg::OnSettingsChanged)
-	ON_BN_CLICKED(IDC_AUTOSAVE_BROWSE,			&PathConfigDlg::OnBrowseAutosavePath)
-	ON_BN_CLICKED(IDC_AUTOSAVE_ENABLE,			&PathConfigDlg::OnAutosaveEnable)
-	ON_BN_CLICKED(IDC_AUTOSAVE_USEORIGDIR,		&PathConfigDlg::OnAutosaveUseOrigDir)
-	ON_BN_CLICKED(IDC_AUTOSAVE_USECUSTOMDIR,	&PathConfigDlg::OnAutosaveUseOrigDir)
-	ON_EN_UPDATE(IDC_AUTOSAVE_PATH,				&PathConfigDlg::OnSettingsChanged)
-	ON_EN_UPDATE(IDC_AUTOSAVE_HISTORY,			&PathConfigDlg::OnSettingsChanged)
-	ON_EN_UPDATE(IDC_AUTOSAVE_INTERVAL,			&PathConfigDlg::OnSettingsChanged)
+	ON_COMMAND(IDC_CHECK1,                &PathConfigDlg::OnSettingsChanged)
+	ON_COMMAND(IDC_CHECK2,                &PathConfigDlg::OnAutosaveRetention)
+	ON_COMMAND(IDC_CHECK3,                &PathConfigDlg::OnSettingsChanged)
+	ON_COMMAND(IDC_AUTOSAVE_BROWSE,       &PathConfigDlg::OnBrowseAutosavePath)
+	ON_COMMAND(IDC_AUTOSAVE_ENABLE,       &PathConfigDlg::OnAutosaveEnable)
+	ON_COMMAND(IDC_AUTOSAVE_USEORIGDIR,   &PathConfigDlg::OnAutosaveUseOrigDir)
+	ON_COMMAND(IDC_AUTOSAVE_USECUSTOMDIR, &PathConfigDlg::OnAutosaveUseOrigDir)
+	ON_EN_UPDATE(IDC_AUTOSAVE_PATH,       &PathConfigDlg::OnSettingsChanged)
+	ON_EN_UPDATE(IDC_AUTOSAVE_HISTORY,    &PathConfigDlg::OnSettingsChanged)
+	ON_EN_UPDATE(IDC_AUTOSAVE_INTERVAL,   &PathConfigDlg::OnSettingsChanged)
+	ON_EN_UPDATE(IDC_EDIT1,               &PathConfigDlg::OnSettingsChanged)
 END_MESSAGE_MAP()
 
 
@@ -101,14 +104,19 @@ BOOL PathConfigDlg::OnInitDialog()
 
 	static_cast<CSpinButtonCtrl *>(GetDlgItem(IDC_SPIN1))->SetRange32(1, int32_max);
 	static_cast<CSpinButtonCtrl *>(GetDlgItem(IDC_SPIN2))->SetRange32(1, int32_max);
+	static_cast<CSpinButtonCtrl *>(GetDlgItem(IDC_SPIN3))->SetRange32(1, int32_max);
 	CheckDlgButton(IDC_AUTOSAVE_ENABLE, settings.AutosaveEnabled ? BST_CHECKED : BST_UNCHECKED);
 	SetDlgItemInt(IDC_AUTOSAVE_HISTORY, settings.AutosaveHistoryDepth);
 	SetDlgItemInt(IDC_AUTOSAVE_INTERVAL, settings.AutosaveIntervalMinutes);
+	SetDlgItemInt(IDC_EDIT1, settings.AutosaveRetentionTimeDays ? settings.AutosaveRetentionTimeDays : 30);
+	CheckDlgButton(IDC_CHECK2, settings.AutosaveRetentionTimeDays > 0);
 	CheckDlgButton(IDC_AUTOSAVE_USEORIGDIR, settings.AutosaveUseOriginalPath ? BST_CHECKED : BST_UNCHECKED);
 	CheckDlgButton(IDC_AUTOSAVE_USECUSTOMDIR, settings.AutosaveUseOriginalPath ? BST_UNCHECKED : BST_CHECKED);
+	CheckDlgButton(IDC_CHECK3, settings.AutosaveDeletePermanently ? BST_CHECKED : BST_UNCHECKED);
 	//enable/disable stuff as appropriate
 	OnAutosaveEnable();
 	OnAutosaveUseOrigDir();
+	OnAutosaveRetention();
 
 	return TRUE;
 }
@@ -132,10 +140,15 @@ void PathConfigDlg::OnOK()
 	// Autosave
 	settings.CreateBackupFiles = IsDlgButtonChecked(IDC_CHECK1) != BST_UNCHECKED;
 
-	settings.AutosaveEnabled = (IsDlgButtonChecked(IDC_AUTOSAVE_ENABLE) != BST_UNCHECKED);
-	settings.AutosaveHistoryDepth = (GetDlgItemInt(IDC_AUTOSAVE_HISTORY));
-	settings.AutosaveIntervalMinutes = (GetDlgItemInt(IDC_AUTOSAVE_INTERVAL));
-	settings.AutosaveUseOriginalPath = (IsDlgButtonChecked(IDC_AUTOSAVE_USEORIGDIR) == BST_CHECKED);
+	settings.AutosaveEnabled = IsDlgButtonChecked(IDC_AUTOSAVE_ENABLE) != BST_UNCHECKED;
+	settings.AutosaveHistoryDepth = GetDlgItemInt(IDC_AUTOSAVE_HISTORY);
+	settings.AutosaveIntervalMinutes = GetDlgItemInt(IDC_AUTOSAVE_INTERVAL);
+	if(IsDlgButtonChecked(IDC_CHECK2))
+		settings.AutosaveRetentionTimeDays = std::max(GetDlgItemInt(IDC_EDIT1), UINT(1));
+	else
+		settings.AutosaveRetentionTimeDays = 0;
+	settings.AutosaveUseOriginalPath = IsDlgButtonChecked(IDC_AUTOSAVE_USEORIGDIR) != BST_UNCHECKED;
+	settings.AutosaveDeletePermanently = IsDlgButtonChecked(IDC_CHECK3) != BST_UNCHECKED;
 
 	CPropertyPage::OnOK();
 }
@@ -157,15 +170,16 @@ void PathConfigDlg::BrowseFolder(UINT nID)
 
 void PathConfigDlg::OnAutosaveEnable()
 {
-	BOOL enabled = IsDlgButtonChecked(IDC_AUTOSAVE_ENABLE);
-	GetDlgItem(IDC_AUTOSAVE_INTERVAL)->EnableWindow(enabled);
-	GetDlgItem(IDC_SPIN1)->EnableWindow(enabled);
-	GetDlgItem(IDC_AUTOSAVE_HISTORY)->EnableWindow(enabled);
-	GetDlgItem(IDC_SPIN2)->EnableWindow(enabled);
-	GetDlgItem(IDC_AUTOSAVE_USEORIGDIR)->EnableWindow(enabled);
-	GetDlgItem(IDC_AUTOSAVE_USECUSTOMDIR)->EnableWindow(enabled);
-	GetDlgItem(IDC_AUTOSAVE_PATH)->EnableWindow(enabled);
-	GetDlgItem(IDC_AUTOSAVE_BROWSE)->EnableWindow(enabled);
+	const BOOL enabled = IsDlgButtonChecked(IDC_AUTOSAVE_ENABLE);
+	static constexpr UINT AutoSaveDlgItems[] =
+	{
+		IDC_AUTOSAVE_INTERVAL, IDC_AUTOSAVE_HISTORY, IDC_AUTOSAVE_USEORIGDIR, IDC_AUTOSAVE_USECUSTOMDIR,
+		IDC_AUTOSAVE_PATH, IDC_AUTOSAVE_BROWSE, IDC_CHECK2, IDC_CHECK3, IDC_EDIT1, IDC_SPIN1, IDC_SPIN2, IDC_SPIN3
+	};
+	for(UINT id : AutoSaveDlgItems)
+	{
+		GetDlgItem(id)->EnableWindow(enabled);
+	}
 	OnSettingsChanged();
 	return;
 }
@@ -173,17 +187,28 @@ void PathConfigDlg::OnAutosaveEnable()
 
 void PathConfigDlg::OnAutosaveUseOrigDir()
 {
-	if (IsDlgButtonChecked(IDC_AUTOSAVE_ENABLE))
+	if(IsDlgButtonChecked(IDC_AUTOSAVE_ENABLE))
 	{
-		BOOL enabled = IsDlgButtonChecked(IDC_AUTOSAVE_USEORIGDIR);
-		GetDlgItem(IDC_AUTOSAVE_PATH)->EnableWindow(!enabled);
-		GetDlgItem(IDC_AUTOSAVE_BROWSE)->EnableWindow(!enabled);
+		const BOOL enabled = IsDlgButtonChecked(IDC_AUTOSAVE_USEORIGDIR) ? FALSE : TRUE;
+		static constexpr UINT AutoSaveDirDlgItems[] = {IDC_AUTOSAVE_PATH, IDC_AUTOSAVE_BROWSE, IDC_CHECK2, IDC_EDIT1, IDC_SPIN3};
+		for(UINT id : AutoSaveDirDlgItems)
+		{
+			GetDlgItem(id)->EnableWindow(enabled);
+		}
 		OnSettingsChanged();
 	}
 	return;
 }
 
 
+void PathConfigDlg::OnAutosaveRetention()
+{
+	const BOOL enabled = IsDlgButtonChecked(IDC_CHECK2) ? TRUE : FALSE;
+	GetDlgItem(IDC_EDIT1)->EnableWindow(enabled);
+	GetDlgItem(IDC_SPIN3)->EnableWindow(enabled);
+}
+
+
 void PathConfigDlg::OnSettingsChanged()
 {
 	SetModified(TRUE);
diff --git a/mptrack/PathConfigDlg.h b/mptrack/PathConfigDlg.h
index a9674d58b7..ca7e5e2ed7 100644
--- a/mptrack/PathConfigDlg.h
+++ b/mptrack/PathConfigDlg.h
@@ -31,6 +31,7 @@ class PathConfigDlg : public CPropertyPage
 
 	afx_msg void OnAutosaveEnable();
 	afx_msg void OnAutosaveUseOrigDir();
+	afx_msg void OnAutosaveRetention();
 	afx_msg void OnBrowseAutosavePath();
 	afx_msg void OnBrowseSongs();
 	afx_msg void OnBrowseSamples();
diff --git a/mptrack/TrackerSettings.cpp b/mptrack/TrackerSettings.cpp
index 9f1242b3de..607be0cda6 100644
--- a/mptrack/TrackerSettings.cpp
+++ b/mptrack/TrackerSettings.cpp
@@ -318,7 +318,9 @@ TrackerSettings::TrackerSettings(SettingsContainer &conf)
 	, AutosaveEnabled(conf, UL_("AutoSave"), UL_("Enabled"), true)
 	, AutosaveIntervalMinutes(conf, UL_("AutoSave"), UL_("IntervalMinutes"), 10)
 	, AutosaveHistoryDepth(conf, UL_("AutoSave"), UL_("BackupHistory"), 3)
+	, AutosaveRetentionTimeDays(conf, UL_("AutoSave"), UL_("RetentionTimeDays"), 30)
 	, AutosaveUseOriginalPath(conf, UL_("AutoSave"), UL_("UseOriginalPath"), true)
+	, AutosaveDeletePermanently(conf, UL_("AutoSave"), UL_("DeletePermanently"), false)
 	, AutosavePath(conf, UL_("AutoSave"), UL_("Path"), mpt::common_directories::get_temp_directory())
 	// Paths
 	, PathSongs(conf, UL_("Paths"), UL_("Songs_Directory"), mpt::PathString())
diff --git a/mptrack/TrackerSettings.h b/mptrack/TrackerSettings.h
index 918bc62d84..c88df59ecd 100644
--- a/mptrack/TrackerSettings.h
+++ b/mptrack/TrackerSettings.h
@@ -886,7 +886,9 @@ class TrackerSettings
 	CachedSetting<bool> AutosaveEnabled;
 	CachedSetting<uint32> AutosaveIntervalMinutes;
 	CachedSetting<uint32> AutosaveHistoryDepth;
+	CachedSetting<uint32> AutosaveRetentionTimeDays;
 	CachedSetting<bool> AutosaveUseOriginalPath;
+	CachedSetting<bool> AutosaveDeletePermanently;
 	ConfigurableDirectory AutosavePath;
 	
 	// Paths
diff --git a/mptrack/mptrack.rc b/mptrack/mptrack.rc
index bbcb0cb8d9..6740e4093f 100644
--- a/mptrack/mptrack.rc
+++ b/mptrack/mptrack.rc
@@ -2188,21 +2188,23 @@ STYLE DS_SETFONT | DS_3DLOOK | DS_FIXEDSYS | WS_CHILD | WS_DISABLED | WS_CAPTION
 CAPTION "Paths / Auto Save"
 FONT 8, "MS Shell Dlg", 0, 0, 0x0
 BEGIN
+    GROUPBOX        "Default Directories",IDC_STATIC,6,6,312,102
     RTEXT           "Songs:",IDC_STATIC_MODDIR,12,18,48,12,SS_CENTERIMAGE
     EDITTEXT        IDC_OPTIONS_DIR_MODS,66,18,192,12,ES_AUTOHSCROLL
-    PUSHBUTTON      "Browse...",IDC_BUTTON_CHANGE_MODDIR,264,18,48,11
+    PUSHBUTTON      "Browse...",IDC_BUTTON_CHANGE_MODDIR,264,18,48,12
     RTEXT           "Samples:",IDC_STATIC_SAMPDIR,12,36,48,12,SS_CENTERIMAGE
     EDITTEXT        IDC_OPTIONS_DIR_SAMPS,66,36,192,12,ES_AUTOHSCROLL
-    PUSHBUTTON      "Browse...",IDC_BUTTON_CHANGE_SAMPDIR,264,36,48,11
+    PUSHBUTTON      "Browse...",IDC_BUTTON_CHANGE_SAMPDIR,264,36,48,12
     RTEXT           "Instruments:",IDC_STATIC_INSTRDIR,12,54,48,12,SS_CENTERIMAGE
     EDITTEXT        IDC_OPTIONS_DIR_INSTS,66,54,192,12,ES_AUTOHSCROLL
-    PUSHBUTTON      "Browse...",IDC_BUTTON_CHANGE_INSTRDIR,264,54,48,11
+    PUSHBUTTON      "Browse...",IDC_BUTTON_CHANGE_INSTRDIR,264,54,48,12
     RTEXT           "VST Plugins:",IDC_STATIC_VSTDIR,12,72,48,12,SS_CENTERIMAGE
     EDITTEXT        IDC_OPTIONS_DIR_VSTS,66,72,192,12,ES_AUTOHSCROLL
-    PUSHBUTTON      "Browse...",IDC_BUTTON_CHANGE_VSTDIR,264,72,48,11
+    PUSHBUTTON      "Browse...",IDC_BUTTON_CHANGE_VSTDIR,264,72,48,12
     RTEXT           "VST Presets:",IDC_STATIC_VSTPRESETDIR,12,90,48,12,SS_CENTERIMAGE
     EDITTEXT        IDC_OPTIONS_DIR_VSTPRESETS,66,90,192,12,ES_AUTOHSCROLL
-    PUSHBUTTON      "Browse...",IDC_BUTTON_CHANGE_VSTPRESETSDIR,264,90,48,11
+    PUSHBUTTON      "Browse...",IDC_BUTTON_CHANGE_VSTPRESETSDIR,264,90,48,12
+    GROUPBOX        "Backup and Auto Save",IDC_STATIC,6,120,312,186
     CONTROL         "Create &backup copy (*.bak) when saving module files",IDC_CHECK1,
                     "Button",BS_AUTOCHECKBOX | WS_TABSTOP,18,135,258,12
     CONTROL         "&Enable Auto Save",IDC_AUTOSAVE_ENABLE,"Button",BS_AUTOCHECKBOX | WS_TABSTOP,18,154,237,10
@@ -2218,12 +2220,16 @@ BEGIN
                     "Button",BS_AUTORADIOBUTTON,18,202,218,10
     CONTROL         "S&tore in:",IDC_AUTOSAVE_USECUSTOMDIR,"Button",BS_AUTORADIOBUTTON,18,218,43,10
     EDITTEXT        IDC_AUTOSAVE_PATH,72,216,186,12,ES_AUTOHSCROLL
-    PUSHBUTTON      "Browse...",IDC_AUTOSAVE_BROWSE,264,216,48,11
-    LTEXT           "Filename:",IDC_STATIC,30,240,36,12,SS_CENTERIMAGE
-    LTEXT           "[filename].AutoSave.[timestamp].[extension]",IDC_STATIC,72,240,240,12,SS_CENTERIMAGE,WS_EX_CLIENTEDGE
-    LTEXT           "(example: mySong.AutoSave.20050327.2343.it)",IDC_STATIC,72,258,240,12,SS_CENTERIMAGE
-    GROUPBOX        "Backup and Auto Save",IDC_STATIC,6,120,312,186
-    GROUPBOX        "Default Directories",IDC_STATIC,6,6,312,102
+    PUSHBUTTON      "Browse...",IDC_AUTOSAVE_BROWSE,264,216,48,12
+    CONTROL         "&Delete auto saves older than",IDC_CHECK2,"Button",BS_AUTOCHECKBOX | WS_TABSTOP,72,234,114,12
+    EDITTEXT        IDC_EDIT1,186,234,40,12,ES_AUTOHSCROLL | ES_NUMBER
+    CONTROL         "",IDC_SPIN3,"msctls_updown32",UDS_SETBUDDYINT | UDS_ALIGNRIGHT | UDS_AUTOBUDDY | UDS_ARROWKEYS | UDS_NOTHOUSANDS,210,240,11,14
+    LTEXT           "days",IDC_STATIC,234,236,30,8
+    CONTROL         "Delete old auto saves &permanently instead of moving them to the recycling bin",IDC_CHECK3,
+                    "Button",BS_AUTOCHECKBOX | WS_TABSTOP,18,252,294,10
+    LTEXT           "Filename:",IDC_STATIC,18,270,36,12,SS_CENTERIMAGE
+    LTEXT           "[filename].AutoSave.[timestamp].[extension]",IDC_STATIC,60,270,252,12,SS_CENTERIMAGE,WS_EX_CLIENTEDGE
+    LTEXT           "(example: mySong.it.AutoSave.20050327.2343.it)",IDC_STATIC,60,288,252,12,SS_CENTERIMAGE
 END
 
 IDD_EDIT_GOTO DIALOGEX 0, 0, 123, 122