diff --git a/osu.Framework.Tests/Visual/UserInterface/TestSceneTooltip.cs b/osu.Framework.Tests/Visual/UserInterface/TestSceneTooltip.cs
index fc5ae4856c..34f81f9a00 100644
--- a/osu.Framework.Tests/Visual/UserInterface/TestSceneTooltip.cs
+++ b/osu.Framework.Tests/Visual/UserInterface/TestSceneTooltip.cs
@@ -265,6 +265,16 @@ private void generateTest(bool cursorlessTooltip)
                                 Text = "with real time updates!",
                                 Size = new Vector2(400, 30),
                             },
+                            new CustomTallTooltipSpriteTextAlt("this one doesn't overlap!")
+                            {
+                                Anchor = Anchor.TopRight,
+                                Origin = Anchor.TopRight,
+                            },
+                            new CustomTallTooltipSpriteText("this one is anchored down and overlaps!")
+                            {
+                                Anchor = Anchor.TopRight,
+                                Origin = Anchor.TopRight,
+                            },
                             new TooltipContainer
                             {
                                 AutoSizeAxes = Axes.Both,
@@ -353,6 +363,26 @@ public CustomTooltipSpriteTextAlt(string displayedContent, string tooltipContent
             public override ITooltip GetCustomTooltip() => new CustomTooltipAlt();
         }
 
+        private partial class CustomTallTooltipSpriteText : CustomTooltipSpriteText
+        {
+            public CustomTallTooltipSpriteText(string displayedContent, string tooltipContent = null)
+                : base(displayedContent, tooltipContent)
+            {
+            }
+
+            public override ITooltip GetCustomTooltip() => new CustomTallTooltip();
+        }
+
+        private partial class CustomTallTooltipSpriteTextAlt : CustomTooltipSpriteText
+        {
+            public CustomTallTooltipSpriteTextAlt(string displayedContent, string tooltipContent = null)
+                : base(displayedContent, tooltipContent)
+            {
+            }
+
+            public override ITooltip GetCustomTooltip() => new CustomTallTooltipAlt();
+        }
+
         private class CustomContent
         {
             public readonly LocalisableString Text;
@@ -367,7 +397,7 @@ private partial class CustomTooltip : CompositeDrawable, ITooltip<CustomContent>
         {
             private static int i;
 
-            private readonly SpriteText text;
+            protected readonly SpriteText Text;
 
             public CustomTooltip()
             {
@@ -380,7 +410,7 @@ public CustomTooltip()
                         RelativeSizeAxes = Axes.Both,
                         Colour = FrameworkColour.GreenDark,
                     },
-                    text = new SpriteText
+                    Text = new SpriteText
                     {
                         Font = FrameworkFont.Regular.With(size: 16),
                         Padding = new MarginPadding(5),
@@ -395,9 +425,10 @@ public CustomTooltip()
                 };
             }
 
-            public void SetContent(CustomContent content) => text.Text = content.Text;
+            public void SetContent(CustomContent content) => Text.Text = content.Text;
 
             public void Move(Vector2 pos) => Position = pos;
+            public virtual bool AllowCursorOverlap => true;
         }
 
         private partial class CustomTooltipAlt : CustomTooltip
@@ -410,6 +441,21 @@ public CustomTooltipAlt()
             }
         }
 
+        private partial class CustomTallTooltip : CustomTooltip
+        {
+            public CustomTallTooltip()
+            {
+                AutoSizeAxes = Axes.Both;
+
+                Text.Width = 0;
+            }
+        }
+
+        private partial class CustomTallTooltipAlt : CustomTallTooltip
+        {
+            public override bool AllowCursorOverlap => false;
+        }
+
         private partial class TooltipSpriteText : Container, IHasTooltip
         {
             public LocalisableString TooltipText { get; }
diff --git a/osu.Framework/Graphics/Cursor/ITooltip.cs b/osu.Framework/Graphics/Cursor/ITooltip.cs
index 2cec948cf0..30afa4b155 100644
--- a/osu.Framework/Graphics/Cursor/ITooltip.cs
+++ b/osu.Framework/Graphics/Cursor/ITooltip.cs
@@ -21,6 +21,16 @@ public interface ITooltip : IDrawable
         /// </summary>
         /// <param name="pos">The position the tooltip should be moved to.</param>
         void Move(Vector2 pos);
+
+        /// <summary>
+        /// Whether to allow the cursor to overlap the tooltip. If true, the tooltip will try to stay anchored
+        /// to the bottom-right of the cursor while keeping itself on screen, potentially overlapping the cursor.
+        /// If false, the tooltip will move to the top-right when the content doesn't fit with the current cursor location.
+        /// </summary>
+        /// <remarks>
+        /// If true, this can be used to avoid abrupt position changes when the content is near the bottom window edge.
+        /// </remarks>
+        bool AllowCursorOverlap { get; }
     }
 
     /// <inheritdoc />
diff --git a/osu.Framework/Graphics/Cursor/TooltipContainer.cs b/osu.Framework/Graphics/Cursor/TooltipContainer.cs
index 3f4c65ab5b..8dc9d84dfc 100644
--- a/osu.Framework/Graphics/Cursor/TooltipContainer.cs
+++ b/osu.Framework/Graphics/Cursor/TooltipContainer.cs
@@ -129,15 +129,23 @@ private Vector2 computeMouseTooltipPosition()
             Vector2 southEast = new Vector2(1).Normalized();
             Vector2 tooltipPos = cursorCentre + southEast * boundingRadius;
 
+            const float edge_padding = 5;
+
             // Clamp position to tooltip container
-            tooltipPos.X = Math.Min(tooltipPos.X, DrawWidth - CurrentTooltip.DrawSize.X - 5);
-            float dX = Math.Max(0, tooltipPos.X - cursorCentre.X);
-            float dY = MathF.Sqrt(boundingRadius * boundingRadius - dX * dX);
+            tooltipPos.X = Math.Min(tooltipPos.X, DrawWidth - CurrentTooltip.DrawSize.X - edge_padding);
 
-            if (tooltipPos.Y > DrawHeight - CurrentTooltip.DrawSize.Y - 5)
-                tooltipPos.Y = cursorCentre.Y - dY - CurrentTooltip.DrawSize.Y;
+            if (CurrentTooltip.AllowCursorOverlap)
+                tooltipPos.Y = Math.Min(tooltipPos.Y, DrawHeight - CurrentTooltip.DrawSize.Y - edge_padding);
             else
-                tooltipPos.Y = cursorCentre.Y + dY;
+            {
+                float dX = Math.Max(0, tooltipPos.X - cursorCentre.X);
+                float dY = MathF.Sqrt(boundingRadius * boundingRadius - dX * dX);
+
+                if (tooltipPos.Y > DrawHeight - CurrentTooltip.DrawSize.Y - edge_padding)
+                    tooltipPos.Y = Math.Max(cursorCentre.Y - dY - CurrentTooltip.DrawSize.Y, edge_padding);
+                else
+                    tooltipPos.Y = cursorCentre.Y + dY;
+            }
 
             return tooltipPos;
         }
@@ -418,6 +426,8 @@ public virtual void Refresh()
             /// </summary>
             /// <param name="pos">The new position of the tooltip.</param>
             public virtual void Move(Vector2 pos) => Position = pos;
+
+            public bool AllowCursorOverlap => false;
         }
     }
 }