diff --git a/osu.Game/Graphics/Containers/SectionsContainer.cs b/osu.Game/Graphics/Containers/SectionsContainer.cs
index b9cb406ae0..8ae619cdc0 100644
--- a/osu.Game/Graphics/Containers/SectionsContainer.cs
+++ b/osu.Game/Graphics/Containers/SectionsContainer.cs
@@ -123,6 +123,8 @@ namespace osu.Game.Graphics.Containers
             originalSectionsMargin = sectionsContainer.Margin;
         }
 
+        public void ScrollTo(Drawable section) => ScrollContainer.ScrollTo(ScrollContainer.GetChildPosInContent(section) - FixedHeader.BoundingBox.Height);
+
         private float lastKnownScroll;
         protected override void UpdateAfterChildren()
         {
diff --git a/osu.Game/OsuGame.cs b/osu.Game/OsuGame.cs
index 961e296050..843861c0da 100644
--- a/osu.Game/OsuGame.cs
+++ b/osu.Game/OsuGame.cs
@@ -56,6 +56,8 @@ namespace osu.Game
             }
         }
 
+        public float ToolbarOffset => Toolbar.Position.Y + Toolbar.DrawHeight;
+
         private OsuScreen screenStack;
 
         private VolumeControl volume;
@@ -360,7 +362,7 @@ namespace osu.Game
         {
             base.UpdateAfterChildren();
 
-            mainContent.Padding = new MarginPadding { Top = Toolbar.Position.Y + Toolbar.DrawHeight };
+            mainContent.Padding = new MarginPadding { Top = ToolbarOffset };
 
             Cursor.State = currentScreen?.HasLocalCursorDisplayed == false ? Visibility.Visible : Visibility.Hidden;
         }
diff --git a/osu.Game/Overlays/Settings/Sidebar.cs b/osu.Game/Overlays/Settings/Sidebar.cs
index 6c91f69fd9..44d296a079 100644
--- a/osu.Game/Overlays/Settings/Sidebar.cs
+++ b/osu.Game/Overlays/Settings/Sidebar.cs
@@ -1,6 +1,8 @@
 // Copyright (c) 2007-2017 ppy Pty Ltd <contact@ppy.sh>.
 // Licensed under the MIT Licence - https://raw.githubusercontent.com/ppy/osu/master/LICENCE
 
+using System.Linq;
+using osu.Framework;
 using OpenTK;
 using OpenTK.Graphics;
 using osu.Framework.Graphics;
@@ -12,7 +14,7 @@ using osu.Game.Overlays.Toolbar;
 
 namespace osu.Game.Overlays.Settings
 {
-    public class Sidebar : Container
+    public class Sidebar : Container, IStateful<ExpandedState>
     {
         private readonly FillFlowContainer content;
         internal const float DEFAULT_WIDTH = ToolbarButton.WIDTH;
@@ -47,24 +49,29 @@ namespace osu.Game.Overlays.Settings
         }
 
         private ScheduledDelegate expandEvent;
+        private ExpandedState state;
 
         protected override bool OnHover(InputState state)
         {
-            expandEvent = Scheduler.AddDelayed(() =>
-            {
-                expandEvent = null;
-                ResizeTo(new Vector2(EXPANDED_WIDTH, Height), 150, EasingTypes.OutQuad);
-            }, 750);
+            queueExpandIfHovering();
             return true;
         }
 
         protected override void OnHoverLost(InputState state)
         {
             expandEvent?.Cancel();
-            ResizeTo(new Vector2(DEFAULT_WIDTH, Height), 150, EasingTypes.OutQuad);
+            lastHoveredButton = null;
+            State = ExpandedState.Contracted;
+
             base.OnHoverLost(state);
         }
 
+        protected override bool OnMouseMove(InputState state)
+        {
+            queueExpandIfHovering();
+            return base.OnMouseMove(state);
+        }
+
         private class SidebarScrollContainer : ScrollContainer
         {
             public SidebarScrollContainer()
@@ -74,5 +81,52 @@ namespace osu.Game.Overlays.Settings
                 RelativeSizeAxes = Axes.Both;
             }
         }
+
+        public ExpandedState State
+        {
+            get { return state; }
+            set
+            {
+                if (state == value) return;
+
+                state = value;
+
+                switch (state)
+                {
+                    default:
+                        ResizeTo(new Vector2(DEFAULT_WIDTH, Height), 500, EasingTypes.OutQuint);
+                        break;
+                    case ExpandedState.Expanded:
+                        ResizeTo(new Vector2(EXPANDED_WIDTH, Height), 500, EasingTypes.OutQuint);
+                        break;
+                }
+            }
+        }
+
+        private Drawable lastHoveredButton;
+
+        private Drawable hoveredButton => content.Children.FirstOrDefault(c => c.IsHovered);
+
+        private void queueExpandIfHovering()
+        {
+            // only expand when we hover a different button.
+            if (lastHoveredButton == hoveredButton) return;
+
+            if (!IsHovered) return;
+
+            if (State != ExpandedState.Expanded)
+            {
+                expandEvent?.Cancel();
+                expandEvent = Scheduler.AddDelayed(() => State = ExpandedState.Expanded, 750);
+            }
+
+            lastHoveredButton = hoveredButton;
+        }
+    }
+
+    public enum ExpandedState
+    {
+        Contracted,
+        Expanded,
     }
 }
\ No newline at end of file
diff --git a/osu.Game/Overlays/SettingsOverlay.cs b/osu.Game/Overlays/SettingsOverlay.cs
index 4a5a0de890..66b15234c3 100644
--- a/osu.Game/Overlays/SettingsOverlay.cs
+++ b/osu.Game/Overlays/SettingsOverlay.cs
@@ -1,6 +1,7 @@
 // Copyright (c) 2007-2017 ppy Pty Ltd <contact@ppy.sh>.
 // Licensed under the MIT Licence - https://raw.githubusercontent.com/ppy/osu/master/LICENCE
 
+using System;
 using System.Linq;
 using OpenTK.Graphics;
 using osu.Framework.Allocation;
@@ -35,6 +36,8 @@ namespace osu.Game.Overlays
 
         private SearchTextBox searchTextBox;
 
+        private Func<float> getToolbarHeight;
+
         public SettingsOverlay()
         {
             RelativeSizeAxes = Axes.Y;
@@ -93,7 +96,11 @@ namespace osu.Game.Overlays
                         new SidebarButton
                         {
                             Section = section,
-                            Action = b => sectionsContainer.ScrollContainer.ScrollTo(b),
+                            Action = s =>
+                            {
+                                sectionsContainer.ScrollTo(s);
+                                sidebar.State = ExpandedState.Contracted;
+                            },
                         }
                     ).ToArray()
                 }
@@ -111,7 +118,7 @@ namespace osu.Game.Overlays
 
             searchTextBox.Current.ValueChanged += newValue => sectionsContainer.SearchContainer.SearchTerm = newValue;
 
-            sectionsContainer.Padding = new MarginPadding { Top = game?.Toolbar.DrawHeight ?? 0 };
+            getToolbarHeight = () => game?.ToolbarOffset ?? 0;
         }
 
         protected override void PopIn()
@@ -148,6 +155,14 @@ namespace osu.Game.Overlays
             base.OnFocus(state);
         }
 
+        protected override void UpdateAfterChildren()
+        {
+            base.UpdateAfterChildren();
+
+            sectionsContainer.Margin = new MarginPadding { Left = sidebar.DrawWidth };
+            sectionsContainer.Padding = new MarginPadding { Top = getToolbarHeight() };
+        }
+
         private class SettingsSectionsContainer : SectionsContainer
         {
             public SearchContainer SearchContainer;