diff --git a/osu.Game.Tests/Visual/UserInterface/TestSceneOsuTooltip.cs b/osu.Game.Tests/Visual/UserInterface/TestSceneOsuTooltip.cs
new file mode 100644
index 0000000000..a2e88bfbc9
--- /dev/null
+++ b/osu.Game.Tests/Visual/UserInterface/TestSceneOsuTooltip.cs
@@ -0,0 +1,86 @@
+// 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.Framework.Graphics;
+using osu.Framework.Graphics.Containers;
+using osu.Framework.Graphics.Cursor;
+using osu.Framework.Graphics.Shapes;
+using osu.Framework.Localisation;
+using osu.Framework.Testing;
+using osu.Game.Graphics;
+using osu.Game.Graphics.Cursor;
+using osu.Game.Graphics.Sprites;
+using osuTK;
+
+namespace osu.Game.Tests.Visual.UserInterface
+{
+    [TestFixture]
+    public partial class TestSceneOsuTooltip : OsuManualInputManagerTestScene
+    {
+        private TestTooltipContainer container = null!;
+
+        private static readonly string[] test_case_tooltip_string =
+        [
+            "Hello!!",
+            string.Concat(Enumerable.Repeat("Hello ", 100)),
+
+            //TODO: o!f issue: https://github.com/ppy/osu-framework/issues/5007
+            //Enable after o!f fixed
+            // $"H{new string('e', 500)}llo",
+        ];
+
+        [SetUp]
+        public void SetUp() => Schedule(() =>
+        {
+            Child = new Container
+            {
+                RelativeSizeAxes = Axes.Both,
+                Padding = new MarginPadding(100),
+                Children = new Drawable[]
+                {
+                    new Box
+                    {
+                        Colour = Colour4.Red.Opacity(0.5f),
+                        RelativeSizeAxes = Axes.Both,
+                    },
+                    container = new TestTooltipContainer
+                    {
+                        RelativeSizeAxes = Axes.Both,
+                        Child = new OsuSpriteText
+                        {
+                            Text = "Hover me!",
+                            Anchor = Anchor.Centre,
+                            Origin = Anchor.Centre,
+                            Font = OsuFont.GetFont(size: 50)
+                        }
+                    },
+                },
+            };
+        });
+
+        [TestCaseSource(nameof(test_case_tooltip_string))]
+        public void TestTooltipBasic(string text)
+        {
+            AddStep("Set tooltip content", () => container.TooltipText = text);
+
+            AddStep("Move mouse to container", () => InputManager.MoveMouseTo(new Vector2(InputManager.ScreenSpaceDrawQuad.Centre.X, InputManager.ScreenSpaceDrawQuad.Centre.Y)));
+
+            OsuTooltipContainer.OsuTooltip? tooltip = null!;
+
+            AddUntilStep("Wait for the tooltip shown", () =>
+            {
+                tooltip = container.FindClosestParent<OsuTooltipContainer>().ChildrenOfType<OsuTooltipContainer.OsuTooltip>().FirstOrDefault();
+                return tooltip != null && tooltip.Alpha == 1;
+            });
+
+            AddAssert("Check tooltip is under width limit", () => tooltip != null && tooltip.Width <= 500);
+        }
+
+        internal sealed partial class TestTooltipContainer : Container, IHasTooltip
+        {
+            public LocalisableString TooltipText { get; set; }
+        }
+    }
+}
diff --git a/osu.Game/Graphics/Cursor/OsuTooltipContainer.cs b/osu.Game/Graphics/Cursor/OsuTooltipContainer.cs
index aab5b3ee36..0d36cc1d08 100644
--- a/osu.Game/Graphics/Cursor/OsuTooltipContainer.cs
+++ b/osu.Game/Graphics/Cursor/OsuTooltipContainer.cs
@@ -10,7 +10,7 @@ using osu.Framework.Graphics.Cursor;
 using osu.Framework.Graphics.Effects;
 using osu.Framework.Graphics.Shapes;
 using osu.Framework.Localisation;
-using osu.Game.Graphics.Sprites;
+using osu.Framework.Graphics.Containers;
 
 namespace osu.Game.Graphics.Cursor
 {
@@ -27,15 +27,20 @@ namespace osu.Game.Graphics.Cursor
 
         public partial class OsuTooltip : Tooltip
         {
+            private const float max_width = 500;
+
             private readonly Box background;
-            private readonly OsuSpriteText text;
+            private readonly TextFlowContainer text;
             private bool instantMovement = true;
 
-            public override void SetContent(LocalisableString contentString)
-            {
-                if (contentString == text.Text) return;
+            private LocalisableString lastContent;
 
-                text.Text = contentString;
+            public override void SetContent(LocalisableString content)
+            {
+                if (content.Equals(lastContent))
+                    return;
+
+                text.Text = content;
 
                 if (IsPresent)
                 {
@@ -44,6 +49,8 @@ namespace osu.Game.Graphics.Cursor
                 }
                 else
                     AutoSizeDuration = 0;
+
+                lastContent = content;
             }
 
             public OsuTooltip()
@@ -65,10 +72,14 @@ namespace osu.Game.Graphics.Cursor
                         RelativeSizeAxes = Axes.Both,
                         Alpha = 0.9f,
                     },
-                    text = new OsuSpriteText
+                    text = new TextFlowContainer(f =>
                     {
-                        Padding = new MarginPadding(5),
-                        Font = OsuFont.GetFont(weight: FontWeight.Regular)
+                        f.Font = OsuFont.GetFont(weight: FontWeight.Regular);
+                    })
+                    {
+                        Margin = new MarginPadding(5),
+                        AutoSizeAxes = Axes.Both,
+                        MaximumSize = new Vector2(max_width, float.PositiveInfinity),
                     }
                 };
             }