diff --git a/osu.Game/Graphics/UserInterface/DrawableOsuMenuItem.cs b/osu.Game/Graphics/UserInterface/DrawableOsuMenuItem.cs
index 20de8e3c9f..cd44bd8fb9 100644
--- a/osu.Game/Graphics/UserInterface/DrawableOsuMenuItem.cs
+++ b/osu.Game/Graphics/UserInterface/DrawableOsuMenuItem.cs
@@ -6,6 +6,7 @@
 using System.Collections.Generic;
 using System.Linq;
 using osu.Framework.Allocation;
+using osu.Framework.Bindables;
 using osu.Framework.Extensions.Color4Extensions;
 using osu.Framework.Graphics;
 using osu.Framework.Graphics.Containers;
@@ -26,6 +27,8 @@ namespace osu.Game.Graphics.UserInterface
         public const int TEXT_SIZE = 17;
         public const int TRANSITION_LENGTH = 80;
 
+        public BindableBool ShowCheckbox { get; } = new BindableBool();
+
         private TextContainer text;
         private HotkeyDisplay hotkey;
         private HoverClickSounds hoverClickSounds;
@@ -72,6 +75,7 @@ namespace osu.Game.Graphics.UserInterface
         {
             base.LoadComplete();
 
+            ShowCheckbox.BindValueChanged(_ => updateState());
             Item.Action.BindDisabledChanged(_ => updateState(), true);
             FinishTransforms();
         }
@@ -138,6 +142,8 @@ namespace osu.Game.Graphics.UserInterface
                 text.BoldText.FadeOut(TRANSITION_LENGTH, Easing.OutQuint);
                 text.NormalText.FadeIn(TRANSITION_LENGTH, Easing.OutQuint);
             }
+
+            text.CheckboxContainer.Alpha = ShowCheckbox.Value ? 1 : 0;
         }
 
         protected sealed override Drawable CreateContent() => text = CreateTextContainer();
diff --git a/osu.Game/Graphics/UserInterface/OsuMenu.cs b/osu.Game/Graphics/UserInterface/OsuMenu.cs
index 2b9a26166f..6e7dad2b5f 100644
--- a/osu.Game/Graphics/UserInterface/OsuMenu.cs
+++ b/osu.Game/Graphics/UserInterface/OsuMenu.cs
@@ -42,6 +42,25 @@ namespace osu.Game.Graphics.UserInterface
             sampleClose = audio.Samples.Get(@"UI/dropdown-close");
         }
 
+        protected override void Update()
+        {
+            base.Update();
+
+            bool showCheckboxes = false;
+
+            foreach (var drawableItem in ItemsContainer)
+            {
+                if (drawableItem.Item is StatefulMenuItem)
+                    showCheckboxes = true;
+            }
+
+            foreach (var drawableItem in ItemsContainer)
+            {
+                if (drawableItem is DrawableOsuMenuItem osuItem)
+                    osuItem.ShowCheckbox.Value = showCheckboxes;
+            }
+        }
+
         protected override void AnimateOpen()
         {
             if (!TopLevelMenu && !wasOpened)