diff --git a/src/apps/mediaplayer/ControllerView.cpp b/src/apps/mediaplayer/ControllerView.cpp
index 6dc2a25d3c..4c9f03499b 100644
--- a/src/apps/mediaplayer/ControllerView.cpp
+++ b/src/apps/mediaplayer/ControllerView.cpp
@@ -98,8 +98,10 @@ void
 ControllerView::TogglePlaying()
 {
 	BAutolock _(fPlaylist);
-	if (fPlaylist->CurrentItemIndex() < 0) {
-		// No valid playlist item - start again from the first one
+	if (fPlaylist->CurrentItemIndex() == fPlaylist->CountItems() - 1
+		&& Position() == 1.0) {
+		// Reached end of playlist and end of last item
+		// -> start again from the first item.
 		fPlaylist->SetCurrentItemIndex(0);
 	} else
 		fController->TogglePlaying();
diff --git a/src/apps/mediaplayer/playlist/Playlist.cpp b/src/apps/mediaplayer/playlist/Playlist.cpp
index b8f014c96e..ba16f10927 100644
--- a/src/apps/mediaplayer/playlist/Playlist.cpp
+++ b/src/apps/mediaplayer/playlist/Playlist.cpp
@@ -352,11 +352,14 @@ bool
 Playlist::SetCurrentItemIndex(int32 index)
 {
 	bool result = true;
-	if (index >= CountItems() || index < 0) {
+	if (index >= CountItems()) {
+		index = CountItems() - 1;
+		result = false;
+	}
+	if (index < 0) {
 		index = -1;
 		result = false;
 	}
-
 	if (index == fCurrentIndex)
 		return result;