diff --git a/src/Avalonia.Controls/ListBox.cs b/src/Avalonia.Controls/ListBox.cs
index 041b81155a..3150b6be91 100644
--- a/src/Avalonia.Controls/ListBox.cs
+++ b/src/Avalonia.Controls/ListBox.cs
@@ -84,6 +84,16 @@ namespace Avalonia.Controls
             set { SetValue(VirtualizationModeProperty, value); }
         }
 
+        /// <summary>
+        /// Selects all items in the <see cref="ListBox"/>.
+        /// </summary>
+        public new void SelectAll() => base.SelectAll();
+
+        /// <summary>
+        /// Deselects all items in the <see cref="ListBox"/>.
+        /// </summary>
+        public new void UnselectAll() => base.UnselectAll();
+
         /// <inheritdoc/>
         protected override IItemContainerGenerator CreateItemContainerGenerator()
         {
@@ -118,7 +128,8 @@ namespace Avalonia.Controls
                     e.Source,
                     true,
                     (e.InputModifiers & InputModifiers.Shift) != 0,
-                    (e.InputModifiers & InputModifiers.Control) != 0);
+                    (e.InputModifiers & InputModifiers.Control) != 0,
+                    e.MouseButton == MouseButton.Right);
             }
         }
 
diff --git a/src/Avalonia.Controls/Primitives/SelectingItemsControl.cs b/src/Avalonia.Controls/Primitives/SelectingItemsControl.cs
index 7b91d6235d..91a9fa7e40 100644
--- a/src/Avalonia.Controls/Primitives/SelectingItemsControl.cs
+++ b/src/Avalonia.Controls/Primitives/SelectingItemsControl.cs
@@ -12,6 +12,7 @@ using Avalonia.Data;
 using Avalonia.Input;
 using Avalonia.Input.Platform;
 using Avalonia.Interactivity;
+using Avalonia.Logging;
 using Avalonia.Styling;
 using Avalonia.VisualTree;
 
@@ -103,6 +104,7 @@ namespace Avalonia.Controls.Primitives
 
         private static readonly IList Empty = Array.Empty<object>();
 
+        private readonly Selection _selection = new Selection();
         private int _selectedIndex = -1;
         private object _selectedItem;
         private IList _selectedItems;
@@ -152,23 +154,8 @@ namespace Avalonia.Controls.Primitives
             {
                 if (_updateCount == 0)
                 {
-                    SetAndRaise(SelectedIndexProperty, ref _selectedIndex, (int val, ref int backing, Action<Action> notifyWrapper) =>
-                    {
-                        var old = backing;
-                        var effective = (val >= 0 && val < Items?.Cast<object>().Count()) ? val : -1;
-
-                        if (old != effective)
-                        {
-                            backing = effective;
-                            notifyWrapper(() =>
-                                RaisePropertyChanged(
-                                    SelectedIndexProperty,
-                                    old,
-                                    effective,
-                                    BindingPriority.LocalValue));
-                            SelectedItem = ElementAt(Items, effective);
-                        }
-                    }, value);
+                    var effective = (value >= 0 && value < ItemCount) ? value : -1;
+                    UpdateSelectedItem(effective);
                 }
                 else
                 {
@@ -192,41 +179,7 @@ namespace Avalonia.Controls.Primitives
             {
                 if (_updateCount == 0)
                 {
-                    SetAndRaise(SelectedItemProperty, ref _selectedItem, (object val, ref object backing, Action<Action> notifyWrapper) =>
-                    {
-                        var old = backing;
-                        var index = IndexOf(Items, val);
-                        var effective = index != -1 ? val : null;
-
-                        if (!object.Equals(effective, old))
-                        {
-                            backing = effective;
-
-                            notifyWrapper(() =>
-                                RaisePropertyChanged(
-                                    SelectedItemProperty,
-                                    old,
-                                    effective,
-                                    BindingPriority.LocalValue));
-
-                            SelectedIndex = index;
-
-                            if (effective != null)
-                            {
-                                if (SelectedItems.Count != 1 || SelectedItems[0] != effective)
-                                {
-                                    _syncingSelectedItems = true;
-                                    SelectedItems.Clear();
-                                    SelectedItems.Add(effective);
-                                    _syncingSelectedItems = false;
-                                }
-                            }
-                            else if (SelectedItems.Count > 0)
-                            {
-                                SelectedItems.Clear();
-                            }
-                        }
-                    }, value);
+                    UpdateSelectedItem(IndexOf(Items, value));
                 }
                 else
                 {
@@ -354,31 +307,23 @@ namespace Avalonia.Controls.Primitives
                     {
                         SelectedIndex = 0;
                     }
+                    else
+                    {
+                        _selection.ItemsInserted(e.NewStartingIndex, e.NewItems.Count);
+                        UpdateSelectedItem(_selection.First(), false);
+                    }
 
                     break;
 
                 case NotifyCollectionChangedAction.Remove:
-                case NotifyCollectionChangedAction.Replace:
-                    var selectedIndex = SelectedIndex;
-
-                    if (selectedIndex >= e.OldStartingIndex &&
-                        selectedIndex < e.OldStartingIndex + e.OldItems.Count)
-                    {
-                        if (!AlwaysSelected)
-                        {
-                            selectedIndex = SelectedIndex = -1;
-                        }
-                        else
-                        {
-                            LostSelection();
-                        }
-                    }
+                    _selection.ItemsRemoved(e.OldStartingIndex, e.OldItems.Count);
+                    UpdateSelectedItem(_selection.First(), false);
+                    ResetSelectedItems();
+                    break;
 
-                    var items = Items?.Cast<object>();
-                    if (selectedIndex >= items.Count())
-                    {
-                        selectedIndex = SelectedIndex = items.Count() - 1;
-                    }
+                case NotifyCollectionChangedAction.Replace:
+                    UpdateSelectedItem(SelectedIndex, false);
+                    ResetSelectedItems();
                     break;
 
                 case NotifyCollectionChangedAction.Move:
@@ -439,11 +384,7 @@ namespace Avalonia.Controls.Primitives
             {
                 if (i.ContainerControl != null && i.Item != null)
                 {
-                    var ms = MemberSelector;
-                    bool selected = ms == null ? 
-                        SelectedItems.Contains(i.Item) : 
-                        SelectedItems.OfType<object>().Any(v => Equals(ms.Select(v), i.Item));
-
+                    bool selected = _selection.Contains(i.Index);
                     MarkContainerSelected(i.ContainerControl, selected);
                 }
             }
@@ -476,9 +417,12 @@ namespace Avalonia.Controls.Primitives
                 var keymap = AvaloniaLocator.Current.GetService<PlatformHotkeyConfiguration>();
                 bool Match(List<KeyGesture> gestures) => gestures.Any(g => g.Matches(e));
 
-                if (this.SelectionMode == SelectionMode.Multiple && Match(keymap.SelectAll))
+                if (ItemCount > 0 &&
+                    Match(keymap.SelectAll) &&
+                    (((SelectionMode & SelectionMode.Multiple) != 0) ||
+                      (SelectionMode & SelectionMode.Toggle) != 0))
                 {
-                    SynchronizeItems(SelectedItems, Items?.Cast<object>());
+                    SelectAll();
                     e.Handled = true;
                 }
             }
@@ -520,6 +464,41 @@ namespace Avalonia.Controls.Primitives
             return false;
         }
 
+        /// <summary>
+        /// Selects all items in the control.
+        /// </summary>
+        protected void SelectAll()
+        {
+            if ((SelectionMode & (SelectionMode.Multiple | SelectionMode.Toggle)) == 0)
+            {
+                throw new NotSupportedException("Multiple selection is not enabled on this control.");
+            }
+
+            UpdateSelectedItems(() =>
+            {
+                _selection.Clear();
+
+                for (var i = 0; i < ItemCount; ++i)
+                {
+                    _selection.Add(i);
+                }
+
+                UpdateSelectedItem(0, false);
+
+                foreach (var container in ItemContainerGenerator.Containers)
+                {
+                    MarkItemSelected(container.Index, true);
+                }
+
+                ResetSelectedItems();
+            });
+        }
+
+        /// <summary>
+        /// Deselects all items in the control.
+        /// </summary>
+        protected void UnselectAll() => UpdateSelectedItem(-1);
+
         /// <summary>
         /// Updates the selection for an item based on user interaction.
         /// </summary>
@@ -527,51 +506,83 @@ namespace Avalonia.Controls.Primitives
         /// <param name="select">Whether the item should be selected or unselected.</param>
         /// <param name="rangeModifier">Whether the range modifier is enabled (i.e. shift key).</param>
         /// <param name="toggleModifier">Whether the toggle modifier is enabled (i.e. ctrl key).</param>
+        /// <param name="rightButton">Whether the event is a right-click.</param>
         protected void UpdateSelection(
             int index,
             bool select = true,
             bool rangeModifier = false,
-            bool toggleModifier = false)
+            bool toggleModifier = false,
+            bool rightButton = false)
         {
             if (index != -1)
             {
                 if (select)
                 {
                     var mode = SelectionMode;
-                    var toggle = toggleModifier || (mode & SelectionMode.Toggle) != 0;
                     var multi = (mode & SelectionMode.Multiple) != 0;
-                    var range = multi && SelectedIndex != -1 && rangeModifier;
+                    var toggle = (toggleModifier || (mode & SelectionMode.Toggle) != 0);
+                    var range = multi && rangeModifier;
 
-                    if (!toggle && !range)
+                    if (range)
                     {
-                        SelectedIndex = index;
-                    }
-                    else if (multi && range)
-                    {
-                        SynchronizeItems(
-                            SelectedItems,
-                            GetRange(Items, SelectedIndex, index));
+                        UpdateSelectedItems(() =>
+                        {
+                            var start = SelectedIndex != -1 ? SelectedIndex : 0;
+                            var step = start < index ? 1 : -1;
+
+                            _selection.Clear();
+
+                            for (var i = start; i != index; i += step)
+                            {
+                                _selection.Add(i);
+                            }
+
+                            _selection.Add(index);
+
+                            var first = Math.Min(start, index);
+                            var last = Math.Max(start, index);
+
+                            foreach (var container in ItemContainerGenerator.Containers)
+                            {
+                                MarkItemSelected(
+                                    container.Index,
+                                    container.Index >= first && container.Index <= last);
+                            }
+
+                            ResetSelectedItems();
+                        });
                     }
-                    else
+                    else if (multi && toggle)
                     {
-                        var item = ElementAt(Items, index);
-                        var i = SelectedItems.IndexOf(item);
-
-                        if (i != -1 && (!AlwaysSelected || SelectedItems.Count > 1))
-                        {
-                            SelectedItems.Remove(item);
-                        }
-                        else
+                        UpdateSelectedItems(() =>
                         {
-                            if (multi)
+                            if (!_selection.Contains(index))
                             {
-                                SelectedItems.Add(item);
+                                _selection.Add(index);
+                                MarkItemSelected(index, true);
+                                SelectedItems.Add(ElementAt(Items, index));
                             }
                             else
                             {
-                                SelectedIndex = index;
+                                _selection.Remove(index);
+                                MarkItemSelected(index, false);
+
+                                if (index == _selectedIndex)
+                                {
+                                    UpdateSelectedItem(_selection.First(), false);
+                                }
+
+                                SelectedItems.Remove(ElementAt(Items, index));
                             }
-                        }
+                        });
+                    }
+                    else if (toggle)
+                    {
+                        SelectedIndex = (SelectedIndex == index) ? -1 : index;
+                    }
+                    else
+                    {
+                        UpdateSelectedItem(index, !(rightButton && _selection.Contains(index)));
                     }
 
                     if (Presenter?.Panel != null)
@@ -596,17 +607,19 @@ namespace Avalonia.Controls.Primitives
         /// <param name="select">Whether the container should be selected or unselected.</param>
         /// <param name="rangeModifier">Whether the range modifier is enabled (i.e. shift key).</param>
         /// <param name="toggleModifier">Whether the toggle modifier is enabled (i.e. ctrl key).</param>
+        /// <param name="rightButton">Whether the event is a right-click.</param>
         protected void UpdateSelection(
             IControl container,
             bool select = true,
             bool rangeModifier = false,
-            bool toggleModifier = false)
+            bool toggleModifier = false,
+            bool rightButton = false)
         {
             var index = ItemContainerGenerator?.IndexFromContainer(container) ?? -1;
 
             if (index != -1)
             {
-                UpdateSelection(index, select, rangeModifier, toggleModifier);
+                UpdateSelection(index, select, rangeModifier, toggleModifier, rightButton);
             }
         }
 
@@ -618,6 +631,7 @@ namespace Avalonia.Controls.Primitives
         /// <param name="select">Whether the container should be selected or unselected.</param>
         /// <param name="rangeModifier">Whether the range modifier is enabled (i.e. shift key).</param>
         /// <param name="toggleModifier">Whether the toggle modifier is enabled (i.e. ctrl key).</param>
+        /// <param name="rightButton">Whether the event is a right-click.</param>
         /// <returns>
         /// True if the event originated from a container that belongs to the control; otherwise
         /// false.
@@ -626,51 +640,20 @@ namespace Avalonia.Controls.Primitives
             IInteractive eventSource,
             bool select = true,
             bool rangeModifier = false,
-            bool toggleModifier = false)
+            bool toggleModifier = false,
+            bool rightButton = false)
         {
             var container = GetContainerFromEventSource(eventSource);
 
             if (container != null)
             {
-                UpdateSelection(container, select, rangeModifier, toggleModifier);
+                UpdateSelection(container, select, rangeModifier, toggleModifier, rightButton);
                 return true;
             }
 
             return false;
         }
 
-        /// <summary>
-        /// Makes a list of objects equal another.
-        /// </summary>
-        /// <param name="items">The items collection.</param>
-        /// <param name="desired">The desired items.</param>
-        internal static void SynchronizeItems(IList items, IEnumerable<object> desired)
-        {
-            var index = 0;
-
-            foreach (object item in desired)
-            {
-                int itemIndex = items.IndexOf(item);
-
-                if (itemIndex == -1)
-                {
-                    items.Insert(index, item);
-                }
-                else if(itemIndex != index)
-                {
-                    items.RemoveAt(itemIndex);
-                    items.Insert(index, item);
-                }
-
-                ++index;
-            }
-
-            while (index < items.Count)
-            {
-                items.RemoveAt(items.Count - 1);
-            }
-        }
-
         /// <summary>
         /// Gets a range of items from an IEnumerable.
         /// </summary>
@@ -678,17 +661,19 @@ namespace Avalonia.Controls.Primitives
         /// <param name="first">The index of the first item.</param>
         /// <param name="last">The index of the last item.</param>
         /// <returns>The items.</returns>
-        private static IEnumerable<object> GetRange(IEnumerable items, int first, int last)
+        private static List<object> GetRange(IEnumerable items, int first, int last)
         {
             var list = (items as IList) ?? items.Cast<object>().ToList();
-            int step = first > last ? -1 : 1;
+            var step = first > last ? -1 : 1;
+            var result = new List<object>();
 
             for (int i = first; i != last; i += step)
             {
-                yield return list[i];
+                result.Add(list[i]);
             }
 
-            yield return list[last];
+            result.Add(list[last]);
+            return result;
         }
 
         /// <summary>
@@ -724,19 +709,14 @@ namespace Avalonia.Controls.Primitives
         private void LostSelection()
         {
             var items = Items?.Cast<object>();
+            var index = -1;
 
             if (items != null && AlwaysSelected)
             {
-                var index = Math.Min(SelectedIndex, items.Count() - 1);
-
-                if (index > -1)
-                {
-                    SelectedItem = items.ElementAt(index);
-                    return;
-                }
+                index = Math.Min(SelectedIndex, items.Count() - 1);
             }
 
-            SelectedIndex = -1;
+            SelectedIndex = index;
         }
 
         /// <summary>
@@ -793,7 +773,7 @@ namespace Avalonia.Controls.Primitives
         /// </summary>
         /// <param name="item">The item.</param>
         /// <param name="selected">Whether the item should be selected or deselected.</param>
-        private void MarkItemSelected(object item, bool selected)
+        private int MarkItemSelected(object item, bool selected)
         {
             var index = IndexOf(Items, item);
 
@@ -801,6 +781,21 @@ namespace Avalonia.Controls.Primitives
             {
                 MarkItemSelected(index, selected);
             }
+
+            return index;
+        }
+
+        private void ResetSelectedItems()
+        {
+            UpdateSelectedItems(() =>
+            {
+                SelectedItems.Clear();
+
+                foreach (var i in _selection)
+                {
+                    SelectedItems.Add(ElementAt(Items, i));
+                }
+            });
         }
 
         /// <summary>
@@ -810,95 +805,97 @@ namespace Avalonia.Controls.Primitives
         /// <param name="e">The event args.</param>
         private void SelectedItemsCollectionChanged(object sender, NotifyCollectionChangedEventArgs e)
         {
-            var generator = ItemContainerGenerator;
+            if (_syncingSelectedItems)
+            {
+                return;
+            }
+
+            void Add(IList newItems, IList addedItems = null)
+            {
+                foreach (var item in newItems)
+                {
+                    var index = MarkItemSelected(item, true);
+
+                    if (index != -1 && _selection.Add(index) && addedItems != null)
+                    {
+                        addedItems.Add(item);
+                    }
+                }
+            }
+
+            void UpdateSelection()
+            {
+                if ((SelectedIndex != -1 && !_selection.Contains(SelectedIndex)) ||
+                    (SelectedIndex == -1 && _selection.HasItems))
+                {
+                    _selectedIndex = _selection.First();
+                    _selectedItem = ElementAt(Items, _selectedIndex);
+                    RaisePropertyChanged(SelectedIndexProperty, -1, _selectedIndex, BindingPriority.LocalValue);
+                    RaisePropertyChanged(SelectedItemProperty, null, _selectedItem, BindingPriority.LocalValue);
+
+                    if (AutoScrollToSelectedItem)
+                    {
+                        ScrollIntoView(_selectedIndex);
+                    }
+                }
+            }
+
             IList added = null;
             IList removed = null;
 
             switch (e.Action)
             {
                 case NotifyCollectionChangedAction.Add:
-                    SelectedItemsAdded(e.NewItems.Cast<object>().ToList());
-
-                    if (AutoScrollToSelectedItem)
                     {
-                        ScrollIntoView(e.NewItems[0]);
+                        Add(e.NewItems);
+                        UpdateSelection();
+                        added = e.NewItems;
                     }
 
-                    added = e.NewItems;
                     break;
 
                 case NotifyCollectionChangedAction.Remove:
                     if (SelectedItems.Count == 0)
                     {
-                        if (!_syncingSelectedItems)
-                        {
-                            SelectedIndex = -1;
-                        }
+                        SelectedIndex = -1;
                     }
 
                     foreach (var item in e.OldItems)
                     {
-                        MarkItemSelected(item, false);
+                        var index = MarkItemSelected(item, false);
+                        _selection.Remove(index);
                     }
 
                     removed = e.OldItems;
                     break;
 
+                case NotifyCollectionChangedAction.Replace:
+                    throw new NotSupportedException("Replacing items in a SelectedItems collection is not supported.");
+
+                case NotifyCollectionChangedAction.Move:
+                    throw new NotSupportedException("Moving items in a SelectedItems collection is not supported.");
+
                 case NotifyCollectionChangedAction.Reset:
-                    if (generator != null)
                     {
                         removed = new List<object>();
+                        added = new List<object>();
 
-                        foreach (var item in generator.Containers)
+                        foreach (var index in _selection.ToList())
                         {
-                            if (item?.ContainerControl != null)
+                            var item = ElementAt(Items, index);
+
+                            if (!SelectedItems.Contains(item))
                             {
-                                if (MarkContainerSelected(item.ContainerControl, false))
-                                {
-                                    removed.Add(item.Item);
-                                }
+                                MarkItemSelected(index, false);
+                                removed.Add(item);
+                                _selection.Remove(index);
                             }
                         }
-                    }
 
-                    if (SelectedItems.Count > 0)
-                    {
-                        _selectedItem = null;
-                        SelectedItemsAdded(SelectedItems);
-                        added = SelectedItems;
-                    }
-                    else if (!_syncingSelectedItems)
-                    {
-                        SelectedIndex = -1;
-                    }
-
-                    break;
-
-                case NotifyCollectionChangedAction.Replace:
-                    foreach (var item in e.OldItems)
-                    {
-                        MarkItemSelected(item, false);
-                    }
-
-                    foreach (var item in e.NewItems)
-                    {
-                        MarkItemSelected(item, true);
+                        Add(SelectedItems, added);
+                        UpdateSelection();
                     }
 
-                    if (SelectedItem != SelectedItems[0] && !_syncingSelectedItems)
-                    {
-                        var oldItem = SelectedItem;
-                        var oldIndex = SelectedIndex;
-                        var item = SelectedItems[0];
-                        var index = IndexOf(Items, item);
-                        _selectedIndex = index;
-                        _selectedItem = item;
-                        RaisePropertyChanged(SelectedIndexProperty, oldIndex, index, BindingPriority.LocalValue);
-                        RaisePropertyChanged(SelectedItemProperty, oldItem, item, BindingPriority.LocalValue);
-                    }
-
-                    added = e.NewItems;
-                    removed = e.OldItems;
                     break;
             }
 
@@ -912,34 +909,6 @@ namespace Avalonia.Controls.Primitives
             }
         }
 
-        /// <summary>
-        /// Called when items are added to the <see cref="SelectedItems"/> collection.
-        /// </summary>
-        /// <param name="items">The added items.</param>
-        private void SelectedItemsAdded(IList items)
-        {
-            if (items.Count > 0)
-            {
-                foreach (var item in items)
-                {
-                    MarkItemSelected(item, true);
-                }
-
-                if (SelectedItem == null && !_syncingSelectedItems)
-                {
-                    var index = IndexOf(Items, items[0]);
-
-                    if (index != -1)
-                    {
-                        _selectedItem = items[0];
-                        _selectedIndex = index;
-                        RaisePropertyChanged(SelectedIndexProperty, -1, index, BindingPriority.LocalValue);
-                        RaisePropertyChanged(SelectedItemProperty, null, items[0], BindingPriority.LocalValue);
-                    }
-                }
-            }
-        }
-
         /// <summary>
         /// Subscribes to the <see cref="SelectedItems"/> CollectionChanged event, if any.
         /// </summary>
@@ -970,6 +939,112 @@ namespace Avalonia.Controls.Primitives
             }
         }
 
+        /// <summary>
+        /// Updates the selection due to a change to <see cref="SelectedIndex"/> or
+        /// <see cref="SelectedItem"/>.
+        /// </summary>
+        /// <param name="index">The new selected index.</param>
+        /// <param name="clear">Whether to clear existing selection.</param>
+        private void UpdateSelectedItem(int index, bool clear = true)
+        {
+            var oldIndex = _selectedIndex;
+            var oldItem = _selectedItem;
+
+            if (index == -1 && AlwaysSelected)
+            {
+                index = Math.Min(SelectedIndex, ItemCount - 1);
+            }
+
+            var item = ElementAt(Items, index);
+            var added = -1;
+            HashSet<int> removed = null;
+
+            _selectedIndex = index;
+            _selectedItem = item;
+
+            if (oldIndex != index || _selection.HasMultiple)
+            {
+                if (clear)
+                {
+                    removed = _selection.Clear();
+                }
+
+                if (index != -1)
+                {
+                    if (_selection.Add(index))
+                    {
+                        added = index;
+                    }
+
+                    if (removed?.Contains(index) == true)
+                    {
+                        removed.Remove(index);
+                        added = -1;
+                    }
+                }
+
+                if (removed != null)
+                {
+                    foreach (var i in removed)
+                    {
+                        MarkItemSelected(i, false);
+                    }
+                }
+
+                MarkItemSelected(index, true);
+
+                RaisePropertyChanged(
+                    SelectedIndexProperty,
+                    oldIndex,
+                    index);
+            }
+
+            if (!Equals(item, oldItem))
+            {
+                RaisePropertyChanged(
+                    SelectedItemProperty,
+                    oldItem,
+                    item);
+            }
+
+            if (removed != null && index != -1)
+            {
+                removed.Remove(index);
+            }
+
+            if (added != -1 || removed?.Count > 0)
+            {
+                ResetSelectedItems();
+
+                var e = new SelectionChangedEventArgs(
+                    SelectionChangedEvent,
+                    added != -1 ? new[] { ElementAt(Items, added) } : Array.Empty<object>(),
+                    removed?.Select(x => ElementAt(Items, x)).ToArray() ?? Array.Empty<object>());
+                RaiseEvent(e);
+            }
+        }
+
+        private void UpdateSelectedItems(Action action)
+        {
+            try
+            {
+                _syncingSelectedItems = true;
+                action();
+            }
+            catch (Exception ex)
+            {
+                Logger.Error(
+                    LogArea.Property,
+                    this,
+                    "Error thrown updating SelectedItems: {Error}",
+                    ex);
+            }
+            finally
+            {
+                _syncingSelectedItems = false;
+            }
+        }
+
         private void UpdateFinished()
         {
             if (_updateSelectedIndex != int.MinValue)
@@ -981,5 +1056,104 @@ namespace Avalonia.Controls.Primitives
                 SelectedItems = _updateSelectedItems;
             }
         }
+
+        private class Selection : IEnumerable<int>
+        {
+            private readonly List<int> _list = new List<int>();
+            private HashSet<int> _set = new HashSet<int>();
+
+            public bool HasItems => _set.Count > 0;
+            public bool HasMultiple => _set.Count > 1;
+
+            public bool Add(int index)
+            {
+                if (index == -1)
+                {
+                    throw new ArgumentException("Invalid index", "index");
+                }
+
+                if (_set.Add(index))
+                {
+                    _list.Add(index);
+                    return true;
+                }
+
+                return false;
+            }
+
+            public bool Remove(int index)
+            {
+                if (_set.Remove(index))
+                {
+                    _list.RemoveAll(x => x == index);
+                    return true;
+                }
+
+                return false;
+            }
+
+            public HashSet<int> Clear()
+            {
+                var result = _set;
+                _list.Clear();
+                _set = new HashSet<int>();
+                return result;
+            }
+
+            public void ItemsInserted(int index, int count)
+            {
+                _set = new HashSet<int>();
+
+                for (var i = 0; i < _list.Count; ++i)
+                {
+                    var ix = _list[i];
+
+                    if (ix >= index)
+                    {
+                        var newIndex = ix + count;
+                        _list[i] = newIndex;
+                        _set.Add(newIndex);
+                    }
+                    else
+                    {
+                        _set.Add(ix);
+                    }
+                }
+            }
+
+            public void ItemsRemoved(int index, int count)
+            {
+                var last = (index + count) - 1;
+
+                _set = new HashSet<int>();
+
+                for (var i = 0; i < _list.Count; ++i)
+                {
+                    var ix = _list[i];
+
+                    if (ix >= index && ix <= last)
+                    {
+                        _list.RemoveAt(i--);
+                    }
+                    else if (ix > last)
+                    {
+                        var newIndex = ix - count;
+                        _list[i] = newIndex;
+                        _set.Add(newIndex);
+                    }
+                    else
+                    {
+                        _set.Add(ix);
+                    }
+                }
+            }
+
+            public bool Contains(int index) => _set.Contains(index);
+
+            public int First() => HasItems ? _list[0] : -1;
+
+            public IEnumerator<int> GetEnumerator() => _set.GetEnumerator();
+            IEnumerator IEnumerable.GetEnumerator() => GetEnumerator();
+        }
     }
 }
diff --git a/src/Avalonia.Controls/TreeView.cs b/src/Avalonia.Controls/TreeView.cs
index c3fbce1d83..888f4a2013 100644
--- a/src/Avalonia.Controls/TreeView.cs
+++ b/src/Avalonia.Controls/TreeView.cs
@@ -409,7 +409,7 @@ namespace Avalonia.Controls
 
                 if (this.SelectionMode == SelectionMode.Multiple && Match(keymap.SelectAll))
                 {
-                    SelectingItemsControl.SynchronizeItems(SelectedItems, ItemContainerGenerator.Index.Items);
+                    SynchronizeItems(SelectedItems, ItemContainerGenerator.Index.Items);
                     e.Handled = true;
                 }
             }
@@ -521,7 +521,7 @@ namespace Avalonia.Controls
             }
             else if (multi && range)
             {
-                SelectingItemsControl.SynchronizeItems(
+                SynchronizeItems(
                     SelectedItems,
                     GetItemsInRange(selectedContainer as TreeViewItem, container as TreeViewItem));
             }
@@ -778,5 +778,27 @@ namespace Avalonia.Controls
                 container.Classes.Set(":selected", selected);
             }
         }
+
+        /// <summary>
+        /// Makes a list of objects equal another (though doesn't preserve order).
+        /// </summary>
+        /// <param name="items">The items collection.</param>
+        /// <param name="desired">The desired items.</param>
+        private static void SynchronizeItems(IList items, IEnumerable<object> desired)
+        {
+            var list = items.Cast<object>().ToList();
+            var toRemove = list.Except(desired).ToList();
+            var toAdd = desired.Except(list).ToList();
+
+            foreach (var i in toRemove)
+            {
+                items.Remove(i);
+            }
+
+            foreach (var i in toAdd)
+            {
+                items.Add(i);
+            }
+        }
     }
 }
diff --git a/tests/Avalonia.Controls.UnitTests/Primitives/SelectingItemsControlTests.cs b/tests/Avalonia.Controls.UnitTests/Primitives/SelectingItemsControlTests.cs
index 8e421bf0a2..75cababf54 100644
--- a/tests/Avalonia.Controls.UnitTests/Primitives/SelectingItemsControlTests.cs
+++ b/tests/Avalonia.Controls.UnitTests/Primitives/SelectingItemsControlTests.cs
@@ -536,6 +536,9 @@ namespace Avalonia.Controls.UnitTests.Primitives
                 SelectedIndex = 1,
             };
 
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+
             var called = false;
 
             target.SelectionChanged += (s, e) =>
@@ -545,8 +548,6 @@ namespace Avalonia.Controls.UnitTests.Primitives
                 called = true;
             };
 
-            target.ApplyTemplate();
-            target.Presenter.ApplyTemplate();
             target.SelectedIndex = -1;
 
             Assert.True(called);
@@ -783,6 +784,116 @@ namespace Avalonia.Controls.UnitTests.Primitives
             Assert.Equal(2, vm.Child.SelectedIndex);
         }
 
+        [Fact]
+        public void Should_Select_Correct_Item_When_Duplicate_Items_Are_Present()
+        {
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz", "Foo", "Bar", "Baz"},
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+            _helper.Down((Interactive)target.Presenter.Panel.Children[3]);
+
+            Assert.Equal(3, target.SelectedIndex);
+        }
+
+        [Fact]
+        public void Should_Apply_Selected_Pseudoclass_To_Correct_Item_When_Duplicate_Items_Are_Present()
+        {
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz", "Foo", "Bar", "Baz" },
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+            _helper.Down((Interactive)target.Presenter.Panel.Children[3]);
+
+            Assert.Equal(new[] { ":selected" }, target.Presenter.Panel.Children[3].Classes);
+        }
+
+        [Fact]
+        public void Adding_Item_Before_SelectedItem_Should_Update_SelectedIndex()
+        {
+            var items = new ObservableCollection<string>
+            {
+               "Foo",
+               "Bar",
+               "Baz"
+            };
+
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = items,
+                SelectedIndex = 1,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+
+            items.Insert(0, "Qux");
+
+            Assert.Equal(2, target.SelectedIndex);
+            Assert.Equal("Bar", target.SelectedItem);
+        }
+
+        [Fact]
+        public void Removing_Item_Before_SelectedItem_Should_Update_SelectedIndex()
+        {
+            var items = new ObservableCollection<string>
+            {
+               "Foo",
+               "Bar",
+               "Baz"
+            };
+
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = items,
+                SelectedIndex = 1,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+
+            items.RemoveAt(0);
+
+            Assert.Equal(0, target.SelectedIndex);
+            Assert.Equal("Bar", target.SelectedItem);
+        }
+
+        [Fact]
+        public void Replacing_Selected_Item_Should_Update_SelectedItem()
+        {
+            var items = new ObservableCollection<string>
+            {
+               "Foo",
+               "Bar",
+               "Baz"
+            };
+
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = items,
+                SelectedIndex = 1,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+
+            items[1] = "Qux";
+
+            Assert.Equal(1, target.SelectedIndex);
+            Assert.Equal("Qux", target.SelectedItem);
+        }
+
         private FuncControlTemplate Template()
         {
             return new FuncControlTemplate<SelectingItemsControl>(control =>
diff --git a/tests/Avalonia.Controls.UnitTests/Primitives/SelectingItemsControlTests_Multiple.cs b/tests/Avalonia.Controls.UnitTests/Primitives/SelectingItemsControlTests_Multiple.cs
index 9ef7d567c8..a33d97779e 100644
--- a/tests/Avalonia.Controls.UnitTests/Primitives/SelectingItemsControlTests_Multiple.cs
+++ b/tests/Avalonia.Controls.UnitTests/Primitives/SelectingItemsControlTests_Multiple.cs
@@ -4,12 +4,15 @@
 using System;
 using System.Collections;
 using System.Collections.Generic;
+using System.Collections.ObjectModel;
 using System.Linq;
 using Avalonia.Collections;
 using Avalonia.Controls.Presenters;
 using Avalonia.Controls.Primitives;
 using Avalonia.Controls.Templates;
 using Avalonia.Data;
+using Avalonia.Input;
+using Avalonia.Interactivity;
 using Avalonia.Markup.Data;
 using Xunit;
 
@@ -17,6 +20,8 @@ namespace Avalonia.Controls.UnitTests.Primitives
 {
     public class SelectingItemsControlTests_Multiple
     {
+        private MouseTestHelper _helper = new MouseTestHelper();
+
         [Fact]
         public void Setting_SelectedIndex_Should_Add_To_SelectedItems()
         {
@@ -258,31 +263,25 @@ namespace Avalonia.Controls.UnitTests.Primitives
         }
 
         [Fact]
-        public void Replacing_First_SelectedItem_Should_Update_SelectedItem_SelectedIndex()
+        public void Setting_SelectedIndex_Should_Unmark_Previously_Selected_Containers()
         {
-            var items = new[]
-            {
-                new ListBoxItem(),
-                new ListBoxItem(),
-                new ListBoxItem(),
-            };
-
             var target = new TestSelector
             {
-                Items = items,
+                Items = new[] { "foo", "bar", "baz" },
                 Template = Template(),
             };
 
             target.ApplyTemplate();
             target.Presenter.ApplyTemplate();
-            target.SelectedIndex = 1;
-            target.SelectedItems[0] = items[2];
 
-            Assert.Equal(2, target.SelectedIndex);
-            Assert.Equal(items[2], target.SelectedItem);
-            Assert.False(items[0].IsSelected);
-            Assert.False(items[1].IsSelected);
-            Assert.True(items[2].IsSelected);
+            target.SelectedItems.Add("foo");
+            target.SelectedItems.Add("bar");
+
+            Assert.Equal(new[] { 0, 1 }, SelectedContainers(target));
+
+            target.SelectedIndex = 2;
+
+            Assert.Equal(new[] { 2 }, SelectedContainers(target));
         }
 
         [Fact]
@@ -361,6 +360,52 @@ namespace Avalonia.Controls.UnitTests.Primitives
             Assert.Equal(new[] { "baz", "qux", "qiz" }, target.SelectedItems.Cast<object>().ToList());
         }
 
+        [Fact]
+        public void Setting_SelectedIndex_After_Range_Should_Unmark_Previously_Selected_Containers()
+        {
+            var target = new TestSelector
+            {
+                Items = new[] { "foo", "bar", "baz", "qux" },
+                Template = Template(),
+                SelectedIndex = 0,
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+
+            target.SelectRange(2);
+
+            Assert.Equal(new[] { 0, 1, 2 }, SelectedContainers(target));
+
+            target.SelectedIndex = 3;
+
+            Assert.Equal(new[] { 3 }, SelectedContainers(target));
+        }
+
+        [Fact]
+        public void Toggling_Selection_After_Range_Should_Work()
+        {
+            var target = new TestSelector
+            {
+                Items = new[] { "foo", "bar", "baz", "foo", "bar", "baz" },
+                Template = Template(),
+                SelectedIndex = 0,
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+
+            target.SelectRange(3);
+
+            Assert.Equal(new[] { 0, 1, 2, 3 }, SelectedContainers(target));
+
+            target.Toggle(4);
+
+            Assert.Equal(new[] { 0, 1, 2, 3, 4 }, SelectedContainers(target));
+        }
+
         [Fact]
         public void Suprious_SelectedIndex_Changes_Should_Not_Be_Triggered()
         {
@@ -382,6 +427,40 @@ namespace Avalonia.Controls.UnitTests.Primitives
             Assert.Equal(new[] { -1, 1, 0 }, selectedIndexes);
         }
 
+        [Fact]
+        public void Can_Set_SelectedIndex_To_Another_Selected_Item()
+        {
+            var target = new TestSelector
+            {
+                Items = new[] { "foo", "bar", "baz" },
+                Template = Template(),
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+            target.SelectedItems.Add("foo");
+            target.SelectedItems.Add("bar");
+
+            Assert.Equal(0, target.SelectedIndex);
+            Assert.Equal(new[] { "foo", "bar" }, target.SelectedItems);
+            Assert.Equal(new[] { 0, 1 }, SelectedContainers(target));
+
+            var raised = false;
+            target.SelectionChanged += (s, e) =>
+            {
+                raised = true;
+                Assert.Empty(e.AddedItems);
+                Assert.Equal(new[] { "foo" }, e.RemovedItems);
+            };
+
+            target.SelectedIndex = 1;
+
+            Assert.True(raised);
+            Assert.Equal(1, target.SelectedIndex);
+            Assert.Equal(new[] { "bar" }, target.SelectedItems);
+            Assert.Equal(new[] { 1 }, SelectedContainers(target));
+        }
+
         /// <summary>
         /// Tests a problem discovered with ListBox with selection.
         /// </summary>
@@ -471,6 +550,7 @@ namespace Avalonia.Controls.UnitTests.Primitives
             {
                 DataContext = items,
                 Template = Template(),
+                Items = items,
             };
 
             var called = false;
@@ -540,35 +620,418 @@ namespace Avalonia.Controls.UnitTests.Primitives
 
             Assert.True(called);
         }
+        
+        [Fact]
+        public void Shift_Selecting_From_No_Selection_Selects_From_Start()
+        {
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz" },
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+            _helper.Click((Interactive)target.Presenter.Panel.Children[2], modifiers: InputModifiers.Shift);
+
+            var panel = target.Presenter.Panel;
+
+            Assert.Equal(new[] { "Foo", "Bar", "Baz" }, target.SelectedItems);
+            Assert.Equal(new[] { 0, 1, 2 }, SelectedContainers(target));
+        }
 
         [Fact]
-        public void Replacing_SelectedItems_Should_Raise_SelectionChanged_With_CorrectItems()
+        public void Ctrl_Selecting_SelectedItem_With_Multiple_Selection_Active_Sets_SelectedItem_To_Next_Selection()
         {
-            var items = new[] { "foo", "bar", "baz" };
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz", "Qux" },
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+            _helper.Click((Interactive)target.Presenter.Panel.Children[1]);
+            _helper.Click((Interactive)target.Presenter.Panel.Children[2], modifiers: InputModifiers.Control);
+            _helper.Click((Interactive)target.Presenter.Panel.Children[3], modifiers: InputModifiers.Control);
+
+            Assert.Equal(1, target.SelectedIndex);
+            Assert.Equal("Bar", target.SelectedItem);
+            Assert.Equal(new[] { "Bar", "Baz", "Qux" }, target.SelectedItems);
+
+            _helper.Click((Interactive)target.Presenter.Panel.Children[1], modifiers: InputModifiers.Control);
+
+            Assert.Equal(2, target.SelectedIndex);
+            Assert.Equal("Baz", target.SelectedItem);
+            Assert.Equal(new[] { "Baz", "Qux" }, target.SelectedItems);
+        }
+
+        [Fact]
+        public void Ctrl_Selecting_Non_SelectedItem_With_Multiple_Selection_Active_Leaves_SelectedItem_The_Same()
+        {
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz" },
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+            _helper.Click((Interactive)target.Presenter.Panel.Children[1]);
+            _helper.Click((Interactive)target.Presenter.Panel.Children[2], modifiers: InputModifiers.Control);
+
+            Assert.Equal(1, target.SelectedIndex);
+            Assert.Equal("Bar", target.SelectedItem);
+
+            _helper.Click((Interactive)target.Presenter.Panel.Children[2], modifiers: InputModifiers.Control);
+
+            Assert.Equal(1, target.SelectedIndex);
+            Assert.Equal("Bar", target.SelectedItem);
+        }
+
+        [Fact]
+        public void Should_Ctrl_Select_Correct_Item_When_Duplicate_Items_Are_Present()
+        {
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz", "Foo", "Bar", "Baz" },
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+            _helper.Click((Interactive)target.Presenter.Panel.Children[3]);
+            _helper.Click((Interactive)target.Presenter.Panel.Children[4], modifiers: InputModifiers.Control);
+
+            var panel = target.Presenter.Panel;
+
+            Assert.Equal(new[] { "Foo", "Bar" }, target.SelectedItems);
+            Assert.Equal(new[] { 3, 4 }, SelectedContainers(target));
+        }
+
+        [Fact]
+        public void Should_Shift_Select_Correct_Item_When_Duplicates_Are_Present()
+        {
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz", "Foo", "Bar", "Baz" },
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+            _helper.Click((Interactive)target.Presenter.Panel.Children[3]);
+            _helper.Click((Interactive)target.Presenter.Panel.Children[5], modifiers: InputModifiers.Shift);
+
+            var panel = target.Presenter.Panel;
 
+            Assert.Equal(new[] { "Foo", "Bar", "Baz" }, target.SelectedItems);
+            Assert.Equal(new[] { 3, 4, 5 }, SelectedContainers(target));
+        }
+
+        [Fact]
+        public void Can_Shift_Select_All_Items_When_Duplicates_Are_Present()
+        {
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz", "Foo", "Bar", "Baz" },
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+            _helper.Click((Interactive)target.Presenter.Panel.Children[0]);
+            _helper.Click((Interactive)target.Presenter.Panel.Children[5], modifiers: InputModifiers.Shift);
+
+            var panel = target.Presenter.Panel;
+
+            Assert.Equal(new[] { "Foo", "Bar", "Baz", "Foo", "Bar", "Baz" }, target.SelectedItems);
+            Assert.Equal(new[] { 0, 1, 2, 3, 4, 5 }, SelectedContainers(target));
+        }
+
+        [Fact]
+        public void Duplicate_Items_Are_Added_To_SelectedItems_In_Order()
+        {
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz", "Foo", "Bar", "Baz" },
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+            _helper.Click((Interactive)target.Presenter.Panel.Children[0]);
+
+            Assert.Equal(new[] { "Foo" }, target.SelectedItems);
+
+            _helper.Click((Interactive)target.Presenter.Panel.Children[4], modifiers: InputModifiers.Control);
+
+            Assert.Equal(new[] { "Foo", "Bar" }, target.SelectedItems);
+
+            _helper.Click((Interactive)target.Presenter.Panel.Children[3], modifiers: InputModifiers.Control);
+
+            Assert.Equal(new[] { "Foo", "Bar", "Foo" }, target.SelectedItems);
+
+            _helper.Click((Interactive)target.Presenter.Panel.Children[1], modifiers: InputModifiers.Control);
+
+            Assert.Equal(new[] { "Foo", "Bar", "Foo", "Bar" }, target.SelectedItems);
+        }
+
+        [Fact]
+        public void SelectAll_Sets_SelectedIndex_And_SelectedItem()
+        {
+            var target = new TestSelector
+            {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz" },
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+
+            target.SelectAll();
+
+            Assert.Equal(0, target.SelectedIndex);
+            Assert.Equal("Foo", target.SelectedItem);
+        }
+
+        [Fact]
+        public void UnselectAll_Clears_SelectedIndex_And_SelectedItem()
+        {
+            var target = new TestSelector
+            {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz" },
+                SelectionMode = SelectionMode.Multiple,
+                SelectedIndex = 0,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+
+            target.UnselectAll();
+
+            Assert.Equal(-1, target.SelectedIndex);
+            Assert.Equal(null, target.SelectedItem);
+        }
+
+        [Fact]
+        public void SelectAll_Handles_Duplicate_Items()
+        {
             var target = new TestSelector
             {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz", "Foo", "Bar", "Baz" },
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+            target.SelectAll();
+
+            Assert.Equal(new[] { "Foo", "Bar", "Baz", "Foo", "Bar", "Baz" }, target.SelectedItems);
+        }
+
+        [Fact]
+        public void Adding_Item_Before_SelectedItems_Should_Update_Selection()
+        {
+            var items = new ObservableCollection<string>
+            {
+               "Foo",
+               "Bar",
+               "Baz"
+            };
+
+            var target = new ListBox
+            {
+                Template = Template(),
                 Items = items,
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+
+            target.SelectAll();
+            items.Insert(0, "Qux");
+
+            Assert.Equal(1, target.SelectedIndex);
+            Assert.Equal("Foo", target.SelectedItem);
+            Assert.Equal(new[] { "Foo", "Bar", "Baz" }, target.SelectedItems);
+            Assert.Equal(new[] { 1, 2, 3 }, SelectedContainers(target));
+        }
+
+        [Fact]
+        public void Removing_Item_Before_SelectedItem_Should_Update_Selection()
+        {
+            var items = new ObservableCollection<string>
+            {
+               "Foo",
+               "Bar",
+               "Baz"
+            };
+
+            var target = new TestSelector
+            {
                 Template = Template(),
-                SelectedItem = "bar",
+                Items = items,
+                SelectionMode = SelectionMode.Multiple,
             };
 
-            var called = false;
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
 
-            target.SelectionChanged += (s, e) =>
+            target.SelectedIndex = 1;
+            target.SelectRange(2);
+
+            Assert.Equal(new[] { "Bar", "Baz" }, target.SelectedItems);
+
+            items.RemoveAt(0);
+
+            Assert.Equal(0, target.SelectedIndex);
+            Assert.Equal("Bar", target.SelectedItem);
+            Assert.Equal(new[] { "Bar", "Baz" }, target.SelectedItems);
+            Assert.Equal(new[] { 0, 1 }, SelectedContainers(target));
+        }
+
+        [Fact]
+        public void Removing_SelectedItem_With_Multiple_Selection_Active_Should_Update_Selection()
+        {
+            var items = new ObservableCollection<string>
             {
-                Assert.Equal(new[] { "foo",}, e.AddedItems.Cast<object>());
-                Assert.Equal(new[] { "bar" }, e.RemovedItems.Cast<object>());
-                called = true;
+               "Foo",
+               "Bar",
+               "Baz"
+            };
+
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = items,
+                SelectionMode = SelectionMode.Multiple,
             };
 
             target.ApplyTemplate();
             target.Presenter.ApplyTemplate();
-            target.SelectedItems[0] = "foo";
 
-            Assert.True(called);
+            target.SelectAll();
+            items.RemoveAt(0);
+
+            Assert.Equal(0, target.SelectedIndex);
+            Assert.Equal("Bar", target.SelectedItem);
+            Assert.Equal(new[] { "Bar", "Baz" }, target.SelectedItems);
+            Assert.Equal(new[] { 0, 1 }, SelectedContainers(target));
         }
 
+        [Fact]
+        public void Replacing_Selected_Item_Should_Update_SelectedItems()
+        {
+            var items = new ObservableCollection<string>
+            {
+               "Foo",
+               "Bar",
+               "Baz"
+            };
+
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = items,
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+
+            target.SelectAll();
+            items[1] = "Qux";
+
+            Assert.Equal(new[] { "Foo", "Qux", "Baz" }, target.SelectedItems);
+        }
+
+        [Fact]
+        public void Left_Click_On_SelectedItem_Should_Clear_Existing_Selection()
+        {
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz" },
+                ItemTemplate = new FuncDataTemplate<string>(x => new TextBlock { Width = 20, Height = 10 }),
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+            target.SelectAll();
+
+            Assert.Equal(3, target.SelectedItems.Count);
+
+            _helper.Click((Interactive)target.Presenter.Panel.Children[0]);
+
+            Assert.Equal(1, target.SelectedItems.Count);
+            Assert.Equal(new[] { "Foo", }, target.SelectedItems);
+            Assert.Equal(new[] { 0 }, SelectedContainers(target));
+        }
+
+        [Fact]
+        public void Right_Click_On_SelectedItem_Should_Not_Clear_Existing_Selection()
+        {
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz" },
+                ItemTemplate = new FuncDataTemplate<string>(x => new TextBlock { Width = 20, Height = 10 }),
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+            target.SelectAll();
+
+            Assert.Equal(3, target.SelectedItems.Count);
+
+            _helper.Click((Interactive)target.Presenter.Panel.Children[0], MouseButton.Right);
+
+            Assert.Equal(3, target.SelectedItems.Count);
+        }
+
+        [Fact]
+        public void Right_Click_On_UnselectedItem_Should_Clear_Existing_Selection()
+        {
+            var target = new ListBox
+            {
+                Template = Template(),
+                Items = new[] { "Foo", "Bar", "Baz" },
+                ItemTemplate = new FuncDataTemplate<string>(x => new TextBlock { Width = 20, Height = 10 }),
+                SelectionMode = SelectionMode.Multiple,
+            };
+
+            target.ApplyTemplate();
+            target.Presenter.ApplyTemplate();
+            _helper.Click((Interactive)target.Presenter.Panel.Children[0]);
+            _helper.Click((Interactive)target.Presenter.Panel.Children[1], modifiers: InputModifiers.Shift);
+
+            Assert.Equal(2, target.SelectedItems.Count);
+
+            _helper.Click((Interactive)target.Presenter.Panel.Children[2], MouseButton.Right);
+
+            Assert.Equal(1, target.SelectedItems.Count);
+        }
+
+        private IEnumerable<int> SelectedContainers(SelectingItemsControl target)
+        {
+            return target.Presenter.Panel.Children
+                .Select((x, i) => x.Classes.Contains(":selected") ? i : -1)
+                .Where(x => x != -1);
+        }
 
         private FuncControlTemplate Template()
         {
@@ -598,10 +1061,10 @@ namespace Avalonia.Controls.UnitTests.Primitives
                 set { base.SelectionMode = value; }
             }
 
-            public void SelectRange(int index)
-            {
-                UpdateSelection(index, true, true);
-            }
+            public new void SelectAll() => base.SelectAll();
+            public new void UnselectAll() => base.UnselectAll();
+            public void SelectRange(int index) => UpdateSelection(index, true, true);
+            public void Toggle(int index) => UpdateSelection(index, true, false, true);
         }
 
         private class OldDataContextViewModel