diff --git a/osu.Game.Rulesets.Mania.Tests/TestSceneHoldNoteInput.cs b/osu.Game.Rulesets.Mania.Tests/TestSceneHoldNoteInput.cs
index 0d13b85901..95072cf4f8 100644
--- a/osu.Game.Rulesets.Mania.Tests/TestSceneHoldNoteInput.cs
+++ b/osu.Game.Rulesets.Mania.Tests/TestSceneHoldNoteInput.cs
@@ -2,6 +2,7 @@
 // See the LICENCE file in the repository root for full licence text.
 
 using System.Collections.Generic;
+using System.Linq;
 using NUnit.Framework;
 using osu.Framework.Screens;
 using osu.Game.Beatmaps;
@@ -10,6 +11,8 @@ using osu.Game.Replays;
 using osu.Game.Rulesets.Judgements;
 using osu.Game.Rulesets.Mania.Objects;
 using osu.Game.Rulesets.Mania.Replays;
+using osu.Game.Rulesets.Mania.Scoring;
+using osu.Game.Rulesets.Objects;
 using osu.Game.Rulesets.Replays;
 using osu.Game.Rulesets.Scoring;
 using osu.Game.Scoring;
@@ -236,6 +239,53 @@ namespace osu.Game.Rulesets.Mania.Tests
             assertTailJudgement(HitResult.Meh);
         }
 
+        [Test]
+        public void TestMissReleaseAndHitSecondRelease()
+        {
+            var windows = new ManiaHitWindows();
+            windows.SetDifficulty(10);
+
+            var beatmap = new Beatmap<ManiaHitObject>
+            {
+                HitObjects =
+                {
+                    new HoldNote
+                    {
+                        StartTime = 1000,
+                        Duration = 500,
+                        Column = 0,
+                    },
+                    new HoldNote
+                    {
+                        StartTime = 1000 + 500 + windows.WindowFor(HitResult.Miss) + 10,
+                        Duration = 500,
+                        Column = 0,
+                    },
+                },
+                BeatmapInfo =
+                {
+                    BaseDifficulty = new BeatmapDifficulty
+                    {
+                        SliderTickRate = 4,
+                        OverallDifficulty = 10,
+                    },
+                    Ruleset = new ManiaRuleset().RulesetInfo
+                },
+            };
+
+            performTest(new List<ReplayFrame>
+            {
+                new ManiaReplayFrame(beatmap.HitObjects[1].StartTime, ManiaAction.Key1),
+                new ManiaReplayFrame(beatmap.HitObjects[1].GetEndTime()),
+            }, beatmap);
+
+            AddAssert("first hold note missed", () => judgementResults.Where(j => beatmap.HitObjects[0].NestedHitObjects.Contains(j.HitObject))
+                                                                      .All(j => j.Type == HitResult.Miss));
+
+            AddAssert("second hold note missed", () => judgementResults.Where(j => beatmap.HitObjects[1].NestedHitObjects.Contains(j.HitObject))
+                                                                       .All(j => j.Type == HitResult.Perfect));
+        }
+
         private void assertHeadJudgement(HitResult result)
             => AddAssert($"head judged as {result}", () => judgementResults[0].Type == result);
 
@@ -250,11 +300,11 @@ namespace osu.Game.Rulesets.Mania.Tests
 
         private ScoreAccessibleReplayPlayer currentPlayer;
 
-        private void performTest(List<ReplayFrame> frames)
+        private void performTest(List<ReplayFrame> frames, Beatmap<ManiaHitObject> beatmap = null)
         {
-            AddStep("load player", () =>
+            if (beatmap == null)
             {
-                Beatmap.Value = CreateWorkingBeatmap(new Beatmap<ManiaHitObject>
+                beatmap = new Beatmap<ManiaHitObject>
                 {
                     HitObjects =
                     {
@@ -270,9 +320,14 @@ namespace osu.Game.Rulesets.Mania.Tests
                         BaseDifficulty = new BeatmapDifficulty { SliderTickRate = 4 },
                         Ruleset = new ManiaRuleset().RulesetInfo
                     },
-                });
+                };
 
-                Beatmap.Value.Beatmap.ControlPointInfo.Add(0, new DifficultyControlPoint { SpeedMultiplier = 0.1f });
+                beatmap.ControlPointInfo.Add(0, new DifficultyControlPoint { SpeedMultiplier = 0.1f });
+            }
+
+            AddStep("load player", () =>
+            {
+                Beatmap.Value = CreateWorkingBeatmap(beatmap);
 
                 var p = new ScoreAccessibleReplayPlayer(new Score { Replay = new Replay { Frames = frames } });
 
diff --git a/osu.Game.Rulesets.Mania/Objects/Drawables/DrawableHoldNote.cs b/osu.Game.Rulesets.Mania/Objects/Drawables/DrawableHoldNote.cs
index 2262bd2b7d..0c5289efe1 100644
--- a/osu.Game.Rulesets.Mania/Objects/Drawables/DrawableHoldNote.cs
+++ b/osu.Game.Rulesets.Mania/Objects/Drawables/DrawableHoldNote.cs
@@ -167,6 +167,12 @@ namespace osu.Game.Rulesets.Mania.Objects.Drawables
             if (action != Action.Value)
                 return false;
 
+            // The tail has a lenience applied to it which is factored into the miss window (i.e. the miss judgement will be delayed).
+            // But the hold cannot ever be started within the late-lenience window, so we should skip trying to begin the hold during that time.
+            // Note: Unlike below, we use the tail's start time to determine the time offset.
+            if (Time.Current > Tail.HitObject.StartTime && !Tail.HitObject.HitWindows.CanBeHit(Time.Current - Tail.HitObject.StartTime))
+                return false;
+
             beginHoldAt(Time.Current - Head.HitObject.StartTime);
             Head.UpdateResult();