diff --git a/src/base_media_base.h b/src/base_media_base.h
--- a/src/base_media_base.h
+++ b/src/base_media_base.h
@@ -301,6 +301,7 @@ struct MusicSongInfo {
 	const char *filename;    ///< file on disk containing song (when used in MusicSet class, this pointer is owned by MD5File object for the file)
 	MusicTrackType filetype; ///< decoder required for song file
 	int cat_index;           ///< entry index in CAT file, for filetype==MTT_MPSMIDI
+	bool loop;               ///< song should play in a tight loop if possible, never ending
 	int override_start;      ///< MIDI ticks to skip over in beginning
 	int override_end;        ///< MIDI tick to end the song at (0 if no override)
 };
diff --git a/src/music/dmusic.cpp b/src/music/dmusic.cpp
--- a/src/music/dmusic.cpp
+++ b/src/music/dmusic.cpp
@@ -832,8 +832,8 @@ static void MidiThreadProc(void *)
 			/* end? */
 			if (current_block == current_file.blocks.size()) {
 				if (current_segment.loop) {
-					current_block = 0;
-					clock->GetTime(&playback_start_time);
+					current_block = current_segment.start_block;
+					playback_start_time = block_time - current_file.blocks[current_block].realtime * MIDITIME_TO_REFTIME;
 				} else {
 					_playback.do_stop = true;
 				}
@@ -1237,7 +1237,7 @@ void MusicDriver_DMusic::PlaySong(const 
 
 	_playback.next_segment.start = song.override_start;
 	_playback.next_segment.end = song.override_end;
-	_playback.next_segment.loop = false;
+	_playback.next_segment.loop = song.loop;
 
 	_playback.do_start = true;
 	SetEvent(_thread_event);
diff --git a/src/music/win32_m.cpp b/src/music/win32_m.cpp
--- a/src/music/win32_m.cpp
+++ b/src/music/win32_m.cpp
@@ -302,8 +302,8 @@ void CALLBACK TimerCallback(UINT uTimerI
 	/* end? */
 	if (_midi.current_block == _midi.current_file.blocks.size()) {
 		if (_midi.current_segment.loop) {
-			_midi.current_block = 0;
-			_midi.playback_start_time = timeGetTime();
+			_midi.current_block = _midi.current_segment.start_block;
+			_midi.playback_start_time = timeGetTime() - _midi.current_file.blocks[_midi.current_block].realtime / 1000;
 		} else {
 			_midi.do_stop = true;
 		}
@@ -322,7 +322,7 @@ void MusicDriver_Win32::PlaySong(const M
 
 	_midi.next_segment.start = song.override_start;
 	_midi.next_segment.end = song.override_end;
-	_midi.next_segment.loop = false;
+	_midi.next_segment.loop = song.loop;
 
 	DEBUG(driver, 2, "Win32-MIDI: PlaySong: setting flag");
 	_midi.do_stop = _midi.playing;
diff --git a/src/music_gui.cpp b/src/music_gui.cpp
--- a/src/music_gui.cpp
+++ b/src/music_gui.cpp
@@ -191,6 +191,7 @@ static void DoPlaySong()
 		FioFindFullPath(filename, lastof(filename), OLD_GM_DIR, songinfo.filename);
 	}
 	songinfo.filename = filename; // non-owned pointer
+	songinfo.loop = (_game_mode == GM_MENU) && (_music_wnd_cursong == 1);
 	MusicDriver::GetInstance()->PlaySong(songinfo);
 	SetWindowDirty(WC_MUSIC_WINDOW, 0);
 }