diff --git a/Userland/Applications/SoundPlayer/Player.cpp b/Userland/Applications/SoundPlayer/Player.cpp
index d9ffbbb86d..153d7060ac 100644
--- a/Userland/Applications/SoundPlayer/Player.cpp
+++ b/Userland/Applications/SoundPlayer/Player.cpp
@@ -48,7 +48,7 @@ void Player::play_file_path(String const& path)
         return;
     }
 
-    if (path.ends_with(".m3u", AK::CaseSensitivity::CaseInsensitive) || path.ends_with(".m3u8", AK::CaseSensitivity::CaseInsensitive)) {
+    if (is_playlist(path)) {
         playlist_loaded(path, m_playlist.load(path));
         return;
     }
@@ -69,6 +69,12 @@ void Player::play_file_path(String const& path)
     play();
 }
 
+bool Player::is_playlist(String const& path)
+{
+    return (path.ends_with(".m3u", AK::CaseSensitivity::CaseInsensitive)
+        || path.ends_with(".m3u8", AK::CaseSensitivity::CaseInsensitive));
+}
+
 void Player::set_play_state(PlayState state)
 {
     if (m_play_state != state) {
diff --git a/Userland/Applications/SoundPlayer/Player.h b/Userland/Applications/SoundPlayer/Player.h
index 1666032384..d215ae6989 100644
--- a/Userland/Applications/SoundPlayer/Player.h
+++ b/Userland/Applications/SoundPlayer/Player.h
@@ -33,6 +33,7 @@ public:
     virtual ~Player() { }
 
     void play_file_path(String const& path);
+    bool is_playlist(String const& path);
 
     Playlist& playlist() { return m_playlist; }
     String const& loaded_filename() const { return m_loaded_filename; }
diff --git a/Userland/Applications/SoundPlayer/main.cpp b/Userland/Applications/SoundPlayer/main.cpp
index 3b0c6b17b1..e7a8a882ba 100644
--- a/Userland/Applications/SoundPlayer/main.cpp
+++ b/Userland/Applications/SoundPlayer/main.cpp
@@ -43,6 +43,8 @@ ErrorOr<int> serenity_main(Main::Arguments arguments)
     if (arguments.argc > 1) {
         StringView path = arguments.strings[1];
         player->play_file_path(path);
+        if (player->is_playlist(path))
+            player->set_loop_mode(Player::LoopMode::Playlist);
     }
 
     auto file_menu = TRY(window->try_add_menu("&File"));
@@ -61,10 +63,9 @@ ErrorOr<int> serenity_main(Main::Arguments arguments)
     auto playback_menu = TRY(window->try_add_menu("&Playback"));
     GUI::ActionGroup loop_actions;
     loop_actions.set_exclusive(true);
-    auto loop_none = TRY(GUI::Action::try_create("&No Loop", [&](auto&) {
+    auto loop_none = GUI::Action::create_checkable("&No Loop", { Mod_Ctrl, Key_N }, [&](auto&) {
         player->set_loop_mode(Player::LoopMode::None);
-    }));
-    loop_none->set_checked(true);
+    });
     loop_actions.add_action(loop_none);
     TRY(playback_menu->try_add_action(loop_none));
 
@@ -90,8 +91,12 @@ ErrorOr<int> serenity_main(Main::Arguments arguments)
     auto playlist_toggle = GUI::Action::create_checkable("&Show Playlist", [&](auto& action) {
         static_cast<SoundPlayerWidgetAdvancedView*>(player)->set_playlist_visible(action.is_checked());
     });
-    if (player->loop_mode() == Player::LoopMode::Playlist)
+    if (player->loop_mode() == Player::LoopMode::Playlist) {
         playlist_toggle->set_checked(true);
+        loop_playlist->set_checked(true);
+    } else {
+        loop_none->set_checked(true);
+    }
     TRY(playback_menu->try_add_action(playlist_toggle));
 
     auto shuffle_mode = GUI::Action::create_checkable("S&huffle Playlist", [&](auto& action) {