diff --git a/src/gui/input.rs b/src/gui/input.rs
index 254b257..dc27399 100644
--- a/src/gui/input.rs
+++ b/src/gui/input.rs
@@ -21,10 +21,17 @@ impl SoundpadGui {
             }
 
             if i.key_pressed(Key::Enter) && self.app_state.selected_file.is_some() {
-                self.play_file(
-                    &self.app_state.selected_file.clone().unwrap(),
-                    i.modifiers.ctrl,
-                );
+                let path = &self.app_state.selected_file.clone().unwrap();
+                if i.modifiers.ctrl {
+                    self.play_file(path, true);
+                } else if i.modifiers.shift
+                    && let Some(last_track) = self.audio_player_state.tracks.last()
+                {
+                    self.stop(Some(last_track.id));
+                    self.play_file(path, true);
+                } else {
+                    self.play_file(path, false);
+                }
             }
 
             if !self.app_state.show_settings {