diff --git a/osu.Game/Screens/Play/SkipOverlay.cs b/osu.Game/Screens/Play/SkipOverlay.cs
index ee05fce730..99fe659bf3 100644
--- a/osu.Game/Screens/Play/SkipOverlay.cs
+++ b/osu.Game/Screens/Play/SkipOverlay.cs
@@ -136,20 +136,29 @@ namespace osu.Game.Screens.Play
             };
 
             fadeContainer.TriggerShow();
-
-            if (skipQueued)
-            {
-                Scheduler.AddDelayed(() => button.TriggerClick(), 200);
-                skipQueued = false;
-            }
         }
 
+        /// <summary>
+        /// Triggers an "automated" skip to happen as soon as available.
+        /// </summary>
         public void SkipWhenReady()
         {
-            if (IsLoaded)
+            if (skipQueued) return;
+
+            skipQueued = true;
+            attemptNextSkip();
+
+            void attemptNextSkip() => Scheduler.AddDelayed(() =>
+            {
+                if (!button.Enabled.Value)
+                {
+                    skipQueued = false;
+                    return;
+                }
+
                 button.TriggerClick();
-            else
-                skipQueued = true;
+                attemptNextSkip();
+            }, 200);
         }
 
         protected override void Update()