diff --git a/osu.Game.Tests/Visual/Gameplay/TestSceneOverlayActivation.cs b/osu.Game.Tests/Visual/Gameplay/TestSceneOverlayActivation.cs
new file mode 100644
index 0000000000..3ee0f4e720
--- /dev/null
+++ b/osu.Game.Tests/Visual/Gameplay/TestSceneOverlayActivation.cs
@@ -0,0 +1,54 @@
+// Copyright (c) ppy Pty Ltd <contact@ppy.sh>. Licensed under the MIT Licence.
+// See the LICENCE file in the repository root for full licence text.
+
+using System.Linq;
+using NUnit.Framework;
+using osu.Game.Overlays;
+using osu.Game.Rulesets;
+
+namespace osu.Game.Tests.Visual.Gameplay
+{
+    public class TestSceneOverlayActivation : OsuPlayerTestScene
+    {
+        protected new OverlayTestPlayer Player => base.Player as OverlayTestPlayer;
+
+        [Test]
+        public void TestGameplayOverlayActivation()
+        {
+            AddAssert("activation mode is disabled", () => Player.OverlayActivationMode == OverlayActivation.Disabled);
+        }
+
+        [Test]
+        public void TestGameplayOverlayActivationPaused()
+        {
+            AddUntilStep("activation mode is disabled", () => Player.OverlayActivationMode == OverlayActivation.Disabled);
+            AddStep("pause gameplay", () => Player.Pause());
+            AddUntilStep("activation mode is user triggered", () => Player.OverlayActivationMode == OverlayActivation.UserTriggered);
+        }
+
+        [Test]
+        public void TestGameplayOverlayActivationReplayLoaded()
+        {
+            AddAssert("activation mode is disabled", () => Player.OverlayActivationMode == OverlayActivation.Disabled);
+            AddStep("load a replay", () => Player.DrawableRuleset.HasReplayLoaded.Value = true);
+            AddAssert("activation mode is user triggered", () => Player.OverlayActivationMode == OverlayActivation.UserTriggered);
+        }
+
+        [Test]
+        public void TestGameplayOverlayActivationBreaks()
+        {
+            AddAssert("activation mode is disabled", () => Player.OverlayActivationMode == OverlayActivation.Disabled);
+            AddStep("seek to break", () => Player.GameplayClockContainer.Seek(Beatmap.Value.Beatmap.Breaks.First().StartTime));
+            AddUntilStep("activation mode is user triggered", () => Player.OverlayActivationMode == OverlayActivation.UserTriggered);
+            AddStep("seek to break end", () => Player.GameplayClockContainer.Seek(Beatmap.Value.Beatmap.Breaks.First().EndTime));
+            AddUntilStep("activation mode is disabled", () => Player.OverlayActivationMode == OverlayActivation.Disabled);
+        }
+
+        protected override TestPlayer CreatePlayer(Ruleset ruleset) => new OverlayTestPlayer();
+
+        protected class OverlayTestPlayer : TestPlayer
+        {
+            public new OverlayActivation OverlayActivationMode => base.OverlayActivationMode.Value;
+        }
+    }
+}
diff --git a/osu.Game/Configuration/OsuConfigManager.cs b/osu.Game/Configuration/OsuConfigManager.cs
index a8a8794320..d49c78183e 100644
--- a/osu.Game/Configuration/OsuConfigManager.cs
+++ b/osu.Game/Configuration/OsuConfigManager.cs
@@ -231,6 +231,6 @@ namespace osu.Game.Configuration
         UIHoldActivationDelay,
         HitLighting,
         MenuBackgroundSource,
-        GameplayDisableWinKey
+        GameplayDisableWinKey,
     }
 }
diff --git a/osu.Game/Screens/Menu/Disclaimer.cs b/osu.Game/Screens/Menu/Disclaimer.cs
index 986de1edf0..fcb9aacd76 100644
--- a/osu.Game/Screens/Menu/Disclaimer.cs
+++ b/osu.Game/Screens/Menu/Disclaimer.cs
@@ -190,7 +190,7 @@ namespace osu.Game.Screens.Menu
             {
                 "You can press Ctrl-T anywhere in the game to toggle the toolbar!",
                 "You can press Ctrl-O anywhere in the game to access options!",
-                "All settings are dynamic and take effect in real-time. Try changing the skin while playing!",
+                "All settings are dynamic and take effect in real-time. Try pausing and changing the skin while playing!",
                 "New features are coming online every update. Make sure to stay up-to-date!",
                 "If you find the UI too large or small, try adjusting UI scale in settings!",
                 "Try adjusting the \"Screen Scaling\" mode to change your gameplay or UI area, even in fullscreen!",
diff --git a/osu.Game/Screens/Play/Player.cs b/osu.Game/Screens/Play/Player.cs
index e78b2a694f..539f9227a3 100644
--- a/osu.Game/Screens/Play/Player.cs
+++ b/osu.Game/Screens/Play/Player.cs
@@ -203,6 +203,10 @@ namespace osu.Game.Screens.Play
                 skipOverlay.Hide();
             }
 
+            DrawableRuleset.IsPaused.BindValueChanged(_ => updateOverlayActivationMode());
+            DrawableRuleset.HasReplayLoaded.BindValueChanged(_ => updateOverlayActivationMode());
+            breakTracker.IsBreakTime.BindValueChanged(_ => updateOverlayActivationMode());
+
             DrawableRuleset.HasReplayLoaded.BindValueChanged(_ => updatePauseOnFocusLostState(), true);
 
             // bind clock into components that require it
@@ -347,6 +351,16 @@ namespace osu.Game.Screens.Play
             HUDOverlay.KeyCounter.IsCounting = !isBreakTime.NewValue;
         }
 
+        private void updateOverlayActivationMode()
+        {
+            bool canTriggerOverlays = DrawableRuleset.IsPaused.Value || breakTracker.IsBreakTime.Value;
+
+            if (DrawableRuleset.HasReplayLoaded.Value || canTriggerOverlays)
+                OverlayActivationMode.Value = OverlayActivation.UserTriggered;
+            else
+                OverlayActivationMode.Value = OverlayActivation.Disabled;
+        }
+
         private void updatePauseOnFocusLostState() =>
             HUDOverlay.HoldToQuit.PauseOnFocusLost = PauseOnFocusLost
                                                      && !DrawableRuleset.HasReplayLoaded.Value
@@ -640,6 +654,8 @@ namespace osu.Game.Screens.Play
             musicController.ResetTrackAdjustments();
             foreach (var mod in Mods.Value.OfType<IApplicableToTrack>())
                 mod.ApplyToTrack(musicController.CurrentTrack);
+
+            updateOverlayActivationMode();
         }
 
         public override void OnSuspending(IScreen next)