diff --git a/osu.Game.Tests/Gameplay/TestSceneProxyContainer.cs b/osu.Game.Tests/Gameplay/TestSceneProxyContainer.cs
new file mode 100644
index 0000000000..1264d575a4
--- /dev/null
+++ b/osu.Game.Tests/Gameplay/TestSceneProxyContainer.cs
@@ -0,0 +1,85 @@
+// 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.Collections.Generic;
+using NUnit.Framework;
+using osu.Framework.Graphics;
+using osu.Framework.Graphics.Containers;
+using osu.Framework.Testing;
+using osu.Framework.Timing;
+using osu.Game.Rulesets.Objects;
+using osu.Game.Rulesets.Objects.Drawables;
+using osu.Game.Rulesets.UI;
+using osu.Game.Tests.Visual;
+
+namespace osu.Game.Tests.Gameplay
+{
+    [HeadlessTest]
+    public class TestSceneProxyContainer : OsuTestScene
+    {
+        private HitObjectContainer hitObjectContainer;
+        private ProxyContainer proxyContainer;
+        private readonly ManualClock clock = new ManualClock();
+
+        [SetUp]
+        public void SetUp() => Schedule(() =>
+        {
+            Child = new Container
+            {
+                Children = new Drawable[]
+                {
+                    hitObjectContainer = new HitObjectContainer(),
+                    proxyContainer = new ProxyContainer()
+                },
+                Clock = new FramedClock(clock)
+            };
+            clock.CurrentTime = 0;
+        });
+
+        [Test]
+        public void TestProxyLifetimeManagement()
+        {
+            AddStep("Add proxy drawables", () =>
+            {
+                addProxy(new TestDrawableHitObject(1000));
+                addProxy(new TestDrawableHitObject(3000));
+                addProxy(new TestDrawableHitObject(5000));
+            });
+
+            AddStep("time = 1000", () => clock.CurrentTime = 1000);
+            AddAssert("One proxy is alive", () => proxyContainer.AliveChildren.Count == 1);
+            AddStep("time = 5000", () => clock.CurrentTime = 5000);
+            AddAssert("One proxy is alive", () => proxyContainer.AliveChildren.Count == 1);
+            AddStep("time = 6000", () => clock.CurrentTime = 6000);
+            AddAssert("No proxy is alive", () => proxyContainer.AliveChildren.Count == 0);
+        }
+
+        private void addProxy(DrawableHitObject drawableHitObject)
+        {
+            hitObjectContainer.Add(drawableHitObject);
+            proxyContainer.AddProxy(drawableHitObject);
+        }
+
+        private class ProxyContainer : LifetimeManagementContainer
+        {
+            public IReadOnlyList<Drawable> AliveChildren => AliveInternalChildren;
+
+            public void AddProxy(Drawable d) => AddInternal(d.CreateProxy());
+        }
+
+        private class TestDrawableHitObject : DrawableHitObject
+        {
+            protected override double InitialLifetimeOffset => 100;
+
+            public TestDrawableHitObject(double startTime)
+                : base(new HitObject { StartTime = startTime })
+            {
+            }
+
+            protected override void UpdateInitialTransforms()
+            {
+                LifetimeEnd = LifetimeStart + 500;
+            }
+        }
+    }
+}
diff --git a/osu.Game/Rulesets/Objects/Pooling/PoolableDrawableWithLifetime.cs b/osu.Game/Rulesets/Objects/Pooling/PoolableDrawableWithLifetime.cs
index ed0430012a..64e1ac16bd 100644
--- a/osu.Game/Rulesets/Objects/Pooling/PoolableDrawableWithLifetime.cs
+++ b/osu.Game/Rulesets/Objects/Pooling/PoolableDrawableWithLifetime.cs
@@ -3,7 +3,6 @@
 
 #nullable enable
 
-using System;
 using System.Diagnostics;
 using osu.Framework.Graphics.Performance;
 using osu.Framework.Graphics.Pooling;
@@ -27,13 +26,14 @@ namespace osu.Game.Rulesets.Objects.Pooling
         /// </summary>
         protected bool HasEntryApplied { get; private set; }
 
+        // Drawable's lifetime gets out of sync with entry's lifetime if entry's lifetime is modified.
+        // We cannot delegate getter to `Entry.LifetimeStart` because it is incompatible with `LifetimeManagementContainer` due to how lifetime change is detected.
         public override double LifetimeStart
         {
-            get => Entry?.LifetimeStart ?? double.MinValue;
+            get => base.LifetimeStart;
             set
             {
-                if (Entry == null && LifetimeStart != value)
-                    throw new InvalidOperationException($"Cannot modify lifetime of {nameof(PoolableDrawableWithLifetime<TEntry>)} when entry is not set");
+                base.LifetimeStart = value;
 
                 if (Entry != null)
                     Entry.LifetimeStart = value;
@@ -42,11 +42,10 @@ namespace osu.Game.Rulesets.Objects.Pooling
 
         public override double LifetimeEnd
         {
-            get => Entry?.LifetimeEnd ?? double.MaxValue;
+            get => base.LifetimeEnd;
             set
             {
-                if (Entry == null && LifetimeEnd != value)
-                    throw new InvalidOperationException($"Cannot modify lifetime of {nameof(PoolableDrawableWithLifetime<TEntry>)} when entry is not set");
+                base.LifetimeEnd = value;
 
                 if (Entry != null)
                     Entry.LifetimeEnd = value;
@@ -80,7 +79,12 @@ namespace osu.Game.Rulesets.Objects.Pooling
                 free();
 
             Entry = entry;
+
+            base.LifetimeStart = entry.LifetimeStart;
+            base.LifetimeEnd = entry.LifetimeEnd;
+
             OnApply(entry);
+
             HasEntryApplied = true;
         }
 
@@ -112,7 +116,11 @@ namespace osu.Game.Rulesets.Objects.Pooling
             Debug.Assert(Entry != null && HasEntryApplied);
 
             OnFree(Entry);
+
             Entry = null;
+            base.LifetimeStart = double.MinValue;
+            base.LifetimeEnd = double.MaxValue;
+
             HasEntryApplied = false;
         }
     }