diff --git a/native/Avalonia.Native/src/OSX/app.mm b/native/Avalonia.Native/src/OSX/app.mm
index 460c24ea3a..e1972b22f4 100644
--- a/native/Avalonia.Native/src/OSX/app.mm
+++ b/native/Avalonia.Native/src/OSX/app.mm
@@ -50,6 +50,12 @@ ComPtr<IAvnApplicationEvents> _events;
     
     _events->FilesOpened(array);
 }
+
+- (NSApplicationTerminateReply)applicationShouldTerminate:(NSApplication *)sender
+{
+    return _events->TryShutdown() ? NSTerminateNow : NSTerminateCancel;
+}
+
 @end
 
 @interface AvnApplication : NSApplication
diff --git a/native/Avalonia.Native/src/OSX/window.mm b/native/Avalonia.Native/src/OSX/window.mm
index 7df9b76425..bb686e3902 100644
--- a/native/Avalonia.Native/src/OSX/window.mm
+++ b/native/Avalonia.Native/src/OSX/window.mm
@@ -2031,18 +2031,7 @@ NSArray* AllLoopModes = [NSArray arrayWithObjects: NSDefaultRunLoopMode, NSEvent
 
 +(void)closeAll
 {
-    NSArray<NSWindow*>* windows = [NSArray arrayWithArray:[NSApp windows]];
-    auto numWindows = [windows count];
-    
-    for(int i = 0; i < numWindows; i++)
-    {
-        auto window = (AvnWindow*)[windows objectAtIndex:i];
-        
-        if([window parentWindow] == nullptr) // Avalonia will handle the child windows.
-        {
-            [window performClose:nil];
-        }
-    }
+    [[NSApplication sharedApplication] terminate:self];
 }
 
 - (void)performClose:(id)sender
diff --git a/samples/ControlCatalog/Pages/ContextFlyoutPage.axaml b/samples/ControlCatalog/Pages/ContextFlyoutPage.axaml
deleted file mode 100644
index f0e079ad91..0000000000
--- a/samples/ControlCatalog/Pages/ContextFlyoutPage.axaml
+++ /dev/null
@@ -1,102 +0,0 @@
-<UserControl xmlns="https://github.com/avaloniaui"
-             xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
-             xmlns:d="http://schemas.microsoft.com/expression/blend/2008"
-             xmlns:mc="http://schemas.openxmlformats.org/markup-compatibility/2006"
-             mc:Ignorable="d" d:DesignWidth="800" d:DesignHeight="450"
-             x:Class="ControlCatalog.Pages.ContextFlyoutPage">
-    <UserControl.Styles>
-        <Style Selector="FlyoutPresenter.NoPadding">
-            <Setter Property="Padding" Value="0" />
-        </Style>
-    </UserControl.Styles>
-    
-    <StackPanel Orientation="Vertical" Spacing="4">
-        <TextBlock Classes="h1">Context Flyout</TextBlock>
-        <TextBlock Classes="h2">A right click Flyout that can be applied to any control.</TextBlock>
-
-        <StackPanel Orientation="Horizontal"
-              Margin="0,16,0,0"
-              HorizontalAlignment="Center"
-              Spacing="16">
-            <Border Background="{DynamicResource SystemAccentColor}"
-                    Margin="16"
-                    Padding="48,48,48,48">
-                <Border.ContextFlyout>
-                    <MenuFlyout>
-                        <MenuItem Header="Standard _Menu Item" InputGesture="Ctrl+A" />
-                        <MenuItem Header="_Disabled Menu Item" IsEnabled="False" InputGesture="Ctrl+D" />
-                        <Separator/>
-                        <MenuItem Header="Menu with _Submenu">
-                            <MenuItem Header="Submenu _1"/>
-                            <MenuItem Header="Submenu _2"/>
-                        </MenuItem>
-                        <MenuItem Header="Menu Item with _Icon" InputGesture="Ctrl+Shift+B">
-                            <MenuItem.Icon>
-                                <Image Source="/Assets/github_icon.png"/>
-                            </MenuItem.Icon>
-                        </MenuItem>
-                        <MenuItem Header="Menu Item with _Checkbox">
-                            <MenuItem.Icon>
-                                <CheckBox BorderThickness="0" IsHitTestVisible="False" IsChecked="True"/>
-                            </MenuItem.Icon>
-                        </MenuItem>
-                    </MenuFlyout>
-                </Border.ContextFlyout>
-                <TextBlock Text="Defined in XAML"/>
-            </Border>
-            <Border Background="{DynamicResource SystemAccentColor}"
-                    Margin="16"
-                    Padding="48,48,48,48">
-                <Border.ContextMenu>
-                    <ContextMenu Items="{Binding MenuItems}">
-                        <ContextMenu.Styles>
-                            <Style Selector="MenuItem">
-                                <Setter Property="Header" Value="{Binding Header}"/>
-                                <Setter Property="Items" Value="{Binding Items}"/>
-                                <Setter Property="Command" Value="{Binding Command}"/>
-                                <Setter Property="CommandParameter" Value="{Binding CommandParameter}"/>
-                            </Style>
-                        </ContextMenu.Styles>
-                    </ContextMenu>
-                </Border.ContextMenu>
-                <TextBlock Text="Dynamically Generated"/>
-            </Border>
-        </StackPanel>
-
-        <TextBlock Text="Custom ContextFlyout for TextBox" />
-
-        <TextBox Name="TextBox" Width="150" HorizontalAlignment="Center" ContextMenu="{x:Null}">
-            <TextBox.ContextFlyout>
-                <Flyout FlyoutPresenterClasses="NoPadding">
-                    <StackPanel Orientation="Horizontal">
-                        <StackPanel.Styles>
-                            <Style Selector="Button">
-                                <Setter Property="Background" Value="Transparent" />
-                                <Setter Property="Height" Value="40" />
-                                <Setter Property="Width" Value="40" />
-                                <Setter Property="VerticalContentAlignment" Value="Center" />
-                            </Style>
-                            <Style Selector="Button:disabled /template/ ContentPresenter#PART_ContentPresenter">
-                                <Setter Property="Background" Value="Transparent" />
-                                <Setter Property="Opacity" Value="0.5" />
-                            </Style>
-                        </StackPanel.Styles>
-                        <Button Name="CutButton" Command="{Binding $parent[TextBox].Cut}" IsEnabled="{Binding $parent[TextBox].CanCut}">
-                            <PathIcon Width="14" Height="14" Data="M5.22774,2.08072 C5.43359778,1.94704 5.7011484,1.98419259 5.86368634,2.15675215 L5.91939,2.22774 L12.5191,12.3904 C12.956,12.1419 13.4614,12.0000019 14,12.0000019 C15.6569,12.0000019 17,13.3431 17,15.0000019 C17,16.6569 15.6569,18.0000019 14,18.0000019 C12.3431,18.0000019 11,16.6569 11,15.0000019 C11,14.3201402 11.226152,13.693011 11.6073785,13.1899092 L11.7401,13.0269 L10,10.3474 L8.25991,13.0269 C8.72078,13.5543 9,14.2446 9,15.0000019 C9,16.6569 7.65685,18.0000019 6,18.0000019 C4.34315,18.0000019 3,16.6569 3,15.0000019 C3,13.3431 4.34315,12.0000019 6,12.0000019 C6.46163143,12.0000019 6.89890041,12.1042536 7.28955831,12.2905296 L7.4809,12.3904 L9.40382,9.42936 L5.08072,2.77238 C4.93033,2.54079 4.99615,2.23112 5.22774,2.08072 Z M14,13 C12.8954,13 12,13.8954 12,15 C12,16.1046 12.8954,17 14,17 C15.1046,17 16,16.1046 16,15 C16,13.8954 15.1046,13 14,13 Z M6,13 C4.89543,13 4,13.8954 4,15 C4,16.1046 4.89543,17 6,17 C7.10457,17 8,16.1046 8,15 C8,13.8954 7.10457,13 6,13 Z M14.7723,2.08072 C15.0039,2.23112 15.0697,2.54079 14.9193,2.77238 L11.1924,8.51133 L10.5962,7.59329 L14.0806,2.22774 C14.231,1.99615 14.5407,1.93033 14.7723,2.08072 Z" />
-                        </Button>
-                        <Button Name="CopyButton" Command="{Binding $parent[TextBox].Copy}" IsEnabled="{Binding $parent[TextBox].CanCopy}">
-                            <PathIcon Width="14" Height="14" Data="M5.50280381,4.62704038 L5.5,6.75 L5.5,17.2542087 C5.5,19.0491342 6.95507456,20.5042087 8.75,20.5042087 L17.3662868,20.5044622 C17.057338,21.3782241 16.2239751,22.0042087 15.2444057,22.0042087 L8.75,22.0042087 C6.12664744,22.0042087 4,19.8775613 4,17.2542087 L4,6.75 C4,5.76928848 4.62744523,4.93512464 5.50280381,4.62704038 Z M17.75,2 C18.9926407,2 20,3.00735931 20,4.25 L20,17.25 C20,18.4926407 18.9926407,19.5 17.75,19.5 L8.75,19.5 C7.50735931,19.5 6.5,18.4926407 6.5,17.25 L6.5,4.25 C6.5,3.00735931 7.50735931,2 8.75,2 L17.75,2 Z M17.75,3.5 L8.75,3.5 C8.33578644,3.5 8,3.83578644 8,4.25 L8,17.25 C8,17.6642136 8.33578644,18 8.75,18 L17.75,18 C18.1642136,18 18.5,17.6642136 18.5,17.25 L18.5,4.25 C18.5,3.83578644 18.1642136,3.5 17.75,3.5 Z" />
-                        </Button>
-                        <Button Name="PasteButton" Command="{Binding $parent[TextBox].Paste}" IsEnabled="{Binding $parent[TextBox].CanPaste}">
-                            <PathIcon Width="14" Height="14" Data="M13.75,2 C14.940864,2 15.9156449,2.92516159 15.9948092,4.09595119 L16,4.25 L16,4.25 C16,4.16530567 15.9953205,4.0817043 15.9862059,3.99944035 L17.75,4 C18.9926407,4 20,5.00735931 20,6.25 L20,19.75 C20,20.9926407 18.9926407,22 17.75,22 L6.25,22 C5.00735931,22 4,20.9926407 4,19.75 L4,6.25 C4,5.00735931 5.00735931,4 6.25,4 L8.01379413,3.99944035 C8.00733496,4.05773764 8.00310309,4.11670658 8.00118552,4.17626017 L8,4.25 C8,3.00735931 9.00735931,2 10.25,2 L13.75,2 Z M13.75,6.5 L10.25,6.5 C9.45594921,6.5 8.75796956,6.08867052 8.357512,5.4674625 L8.37902077,5.50019943 L8.37902077,5.50019943 L6.25,5.5 C5.83578644,5.5 5.5,5.83578644 5.5,6.25 L5.5,19.75 C5.5,20.1642136 5.83578644,20.5 6.25,20.5 L17.75,20.5 C18.1642136,20.5 18.5,20.1642136 18.5,19.75 L18.5,6.25 C18.5,5.83578644 18.1642136,5.5 17.75,5.5 L15.6209792,5.50019943 L15.642488,5.4674625 C15.2420304,6.08867052 14.5440508,6.5 13.75,6.5 Z M13.75,3.5 L10.25,3.5 C9.83578644,3.5 9.5,3.83578644 9.5,4.25 C9.5,4.66421356 9.83578644,5 10.25,5 L13.75,5 C14.1642136,5 14.5,4.66421356 14.5,4.25 C14.5,3.83578644 14.1642136,3.5 13.75,3.5 Z" />
-                        </Button>
-                        <Button Name="ClearButton" Command="{Binding $parent[TextBox].Clear}">
-                            <PathIcon Width="14" Height="14" Data="M3.52499419,3.71761187 L3.61611652,3.61611652 C4.0717282,3.16050485 4.79154862,3.13013074 5.28238813,3.52499419 L5.38388348,3.61611652 L14,12.233 L22.6161165,3.61611652 C23.1042719,3.12796116 23.8957281,3.12796116 24.3838835,3.61611652 C24.8720388,4.10427189 24.8720388,4.89572811 24.3838835,5.38388348 L15.767,14 L24.3838835,22.6161165 C24.8394952,23.0717282 24.8698693,23.7915486 24.4750058,24.2823881 L24.3838835,24.3838835 C23.9282718,24.8394952 23.2084514,24.8698693 22.7176119,24.4750058 L22.6161165,24.3838835 L14,15.767 L5.38388348,24.3838835 C4.89572811,24.8720388 4.10427189,24.8720388 3.61611652,24.3838835 C3.12796116,23.8957281 3.12796116,23.1042719 3.61611652,22.6161165 L12.233,14 L3.61611652,5.38388348 C3.16050485,4.9282718 3.13013074,4.20845138 3.52499419,3.71761187 L3.61611652,3.61611652 L3.52499419,3.71761187 Z" />
-                        </Button>
-                    </StackPanel>
-                </Flyout>
-            </TextBox.ContextFlyout>
-        </TextBox>
-    
-    </StackPanel>
-</UserControl>
diff --git a/samples/ControlCatalog/Pages/ContextFlyoutPage.axaml.cs b/samples/ControlCatalog/Pages/ContextFlyoutPage.axaml.cs
deleted file mode 100644
index e64d4a2cdd..0000000000
--- a/samples/ControlCatalog/Pages/ContextFlyoutPage.axaml.cs
+++ /dev/null
@@ -1,45 +0,0 @@
-using Avalonia;
-using Avalonia.Controls;
-using Avalonia.Markup.Xaml;
-using ControlCatalog.ViewModels;
-using Avalonia.Interactivity;
-namespace ControlCatalog.Pages
-{
-    public class ContextFlyoutPage : UserControl
-    {
-        private TextBox _textBox;
-
-        public ContextFlyoutPage()
-        {
-            InitializeComponent();
-
-            var vm = new ContextFlyoutPageViewModel();
-            vm.View = this;
-            DataContext = vm;
-
-            _textBox = this.FindControl<TextBox>("TextBox");
-
-            var cutButton = this.FindControl<Button>("CutButton");
-            cutButton.Click += CloseFlyout;
-
-            var copyButton = this.FindControl<Button>("CopyButton");
-            copyButton.Click += CloseFlyout;
-
-            var pasteButton = this.FindControl<Button>("PasteButton");
-            pasteButton.Click += CloseFlyout;
-
-            var clearButton = this.FindControl<Button>("ClearButton");
-            clearButton.Click += CloseFlyout;
-        }
-
-        private void CloseFlyout(object sender, RoutedEventArgs e)
-        {
-            _textBox.ContextFlyout.Hide();
-        }
-
-        private void InitializeComponent()
-        {
-            AvaloniaXamlLoader.Load(this);
-        }
-    }
-}
diff --git a/samples/ControlCatalog/Pages/ContextFlyoutPage.xaml b/samples/ControlCatalog/Pages/ContextFlyoutPage.xaml
new file mode 100644
index 0000000000..0d9026bdd5
--- /dev/null
+++ b/samples/ControlCatalog/Pages/ContextFlyoutPage.xaml
@@ -0,0 +1,157 @@
+<UserControl x:Class="ControlCatalog.Pages.ContextFlyoutPage"
+             xmlns="https://github.com/avaloniaui"
+             xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
+             xmlns:d="http://schemas.microsoft.com/expression/blend/2008"
+             xmlns:mc="http://schemas.openxmlformats.org/markup-compatibility/2006"
+             d:DesignHeight="450"
+             d:DesignWidth="800"
+             mc:Ignorable="d">
+  <UserControl.Styles>
+    <Style Selector="FlyoutPresenter.NoPadding">
+      <Setter Property="Padding" Value="0" />
+    </Style>
+  </UserControl.Styles>
+
+  <StackPanel Orientation="Vertical" Spacing="4">
+    <StackPanel.Styles>
+      <Style Selector="Border.context-target">
+        <Setter Property="Padding" Value="48,20" />
+        <Setter Property="Margin" Value="8" />
+        <Setter Property="Focusable" Value="True" />
+        <Setter Property="Background" Value="{DynamicResource SystemAccentColor}" />
+      </Style>
+      <Style Selector="Border.context-target > :is(Control)">
+        <Setter Property="VerticalAlignment" Value="Center" />
+      </Style>
+    </StackPanel.Styles>
+    <TextBlock Classes="h1">Context Flyout</TextBlock>
+    <TextBlock Classes="h2">A right click Flyout that can be applied to any control.</TextBlock>
+
+    <UniformGrid HorizontalAlignment="Center" Rows="2">
+      <Border Classes="context-target">
+        <Border.ContextFlyout>
+          <MenuFlyout>
+            <MenuItem Header="Standard _Menu Item" InputGesture="Ctrl+A" />
+            <MenuItem Header="_Disabled Menu Item"
+                      InputGesture="Ctrl+D"
+                      IsEnabled="False" />
+            <Separator />
+            <MenuItem Header="Menu with _Submenu">
+              <MenuItem Header="Submenu _1" />
+              <MenuItem Header="Submenu _2" />
+            </MenuItem>
+            <MenuItem Header="Menu Item with _Icon" InputGesture="Ctrl+Shift+B">
+              <MenuItem.Icon>
+                <Image Source="/Assets/github_icon.png" />
+              </MenuItem.Icon>
+            </MenuItem>
+            <MenuItem Header="Menu Item with _Checkbox">
+              <MenuItem.Icon>
+                <CheckBox BorderThickness="0"
+                          IsChecked="True"
+                          IsHitTestVisible="False" />
+              </MenuItem.Icon>
+            </MenuItem>
+          </MenuFlyout>
+        </Border.ContextFlyout>
+        <TextBlock Text="Defined in XAML" />
+      </Border>
+      <Border Classes="context-target">
+        <Border.Styles>
+          <Style Selector="MenuFlyoutPresenter MenuItem">
+            <Setter Property="Header" Value="{Binding Header}"/>
+            <Setter Property="Items" Value="{Binding Items}"/>
+            <Setter Property="Command" Value="{Binding Command}"/>
+            <Setter Property="CommandParameter" Value="{Binding CommandParameter}"/>
+          </Style>
+        </Border.Styles>
+        <Border.ContextFlyout>
+          <MenuFlyout Items="{Binding MenuItems}" />
+        </Border.ContextFlyout>
+        <TextBlock Text="Dynamically Generated"/>
+      </Border>
+      <Border x:Name="CustomContextRequestedBorder"
+              Classes="context-target">
+        <Border.ContextFlyout>
+          <Flyout Content="Should never be visible" />
+        </Border.ContextFlyout>
+        <TextBlock Text="Custom ContextRequested handler" TextWrapping="Wrap" />
+      </Border>
+      <Border x:Name="CancellableContextBorder"
+              Classes="context-target">
+        <Border.ContextFlyout>
+          <Flyout>
+            <CheckBox x:Name="CancelCloseCheckBox" Content="Cancel close" />
+          </Flyout>
+        </Border.ContextFlyout>
+        <StackPanel>
+          <TextBlock Text="Cancellable" />
+          <CheckBox x:Name="CancelOpenCheckBox" Content="Cancel open" />
+        </StackPanel>
+      </Border>
+    </UniformGrid>
+
+    <TextBlock Text="Custom ContextFlyout for TextBox" />
+
+    <TextBox Name="TextBox"
+             Width="150"
+             HorizontalAlignment="Center"
+             ContextMenu="{x:Null}">
+      <TextBox.ContextFlyout>
+        <Flyout FlyoutPresenterClasses="NoPadding">
+          <StackPanel>
+          <StackPanel Orientation="Horizontal">
+            <StackPanel.Styles>
+              <Style Selector="Button">
+                <Setter Property="Background" Value="Transparent" />
+                <Setter Property="Height" Value="40" />
+                <Setter Property="Width" Value="40" />
+                <Setter Property="VerticalContentAlignment" Value="Center" />
+              </Style>
+              <Style Selector="Button:disabled /template/ ContentPresenter#PART_ContentPresenter">
+                <Setter Property="Background" Value="Transparent" />
+                <Setter Property="Opacity" Value="0.5" />
+              </Style>
+            </StackPanel.Styles>
+            <Button Name="CutButton"
+                    Command="{Binding $parent[TextBox].Cut}"
+                    IsEnabled="{Binding $parent[TextBox].CanCut}">
+              <PathIcon Width="14"
+                        Height="14"
+                        Data="M5.22774,2.08072 C5.43359778,1.94704 5.7011484,1.98419259 5.86368634,2.15675215 L5.91939,2.22774 L12.5191,12.3904 C12.956,12.1419 13.4614,12.0000019 14,12.0000019 C15.6569,12.0000019 17,13.3431 17,15.0000019 C17,16.6569 15.6569,18.0000019 14,18.0000019 C12.3431,18.0000019 11,16.6569 11,15.0000019 C11,14.3201402 11.226152,13.693011 11.6073785,13.1899092 L11.7401,13.0269 L10,10.3474 L8.25991,13.0269 C8.72078,13.5543 9,14.2446 9,15.0000019 C9,16.6569 7.65685,18.0000019 6,18.0000019 C4.34315,18.0000019 3,16.6569 3,15.0000019 C3,13.3431 4.34315,12.0000019 6,12.0000019 C6.46163143,12.0000019 6.89890041,12.1042536 7.28955831,12.2905296 L7.4809,12.3904 L9.40382,9.42936 L5.08072,2.77238 C4.93033,2.54079 4.99615,2.23112 5.22774,2.08072 Z M14,13 C12.8954,13 12,13.8954 12,15 C12,16.1046 12.8954,17 14,17 C15.1046,17 16,16.1046 16,15 C16,13.8954 15.1046,13 14,13 Z M6,13 C4.89543,13 4,13.8954 4,15 C4,16.1046 4.89543,17 6,17 C7.10457,17 8,16.1046 8,15 C8,13.8954 7.10457,13 6,13 Z M14.7723,2.08072 C15.0039,2.23112 15.0697,2.54079 14.9193,2.77238 L11.1924,8.51133 L10.5962,7.59329 L14.0806,2.22774 C14.231,1.99615 14.5407,1.93033 14.7723,2.08072 Z" />
+            </Button>
+            <Button Name="CopyButton"
+                    Command="{Binding $parent[TextBox].Copy}"
+                    IsEnabled="{Binding $parent[TextBox].CanCopy}">
+              <PathIcon Width="14"
+                        Height="14"
+                        Data="M5.50280381,4.62704038 L5.5,6.75 L5.5,17.2542087 C5.5,19.0491342 6.95507456,20.5042087 8.75,20.5042087 L17.3662868,20.5044622 C17.057338,21.3782241 16.2239751,22.0042087 15.2444057,22.0042087 L8.75,22.0042087 C6.12664744,22.0042087 4,19.8775613 4,17.2542087 L4,6.75 C4,5.76928848 4.62744523,4.93512464 5.50280381,4.62704038 Z M17.75,2 C18.9926407,2 20,3.00735931 20,4.25 L20,17.25 C20,18.4926407 18.9926407,19.5 17.75,19.5 L8.75,19.5 C7.50735931,19.5 6.5,18.4926407 6.5,17.25 L6.5,4.25 C6.5,3.00735931 7.50735931,2 8.75,2 L17.75,2 Z M17.75,3.5 L8.75,3.5 C8.33578644,3.5 8,3.83578644 8,4.25 L8,17.25 C8,17.6642136 8.33578644,18 8.75,18 L17.75,18 C18.1642136,18 18.5,17.6642136 18.5,17.25 L18.5,4.25 C18.5,3.83578644 18.1642136,3.5 17.75,3.5 Z" />
+            </Button>
+            <Button Name="PasteButton"
+                    Command="{Binding $parent[TextBox].Paste}"
+                    IsEnabled="{Binding $parent[TextBox].CanPaste}">
+              <PathIcon Width="14"
+                        Height="14"
+                        Data="M13.75,2 C14.940864,2 15.9156449,2.92516159 15.9948092,4.09595119 L16,4.25 L16,4.25 C16,4.16530567 15.9953205,4.0817043 15.9862059,3.99944035 L17.75,4 C18.9926407,4 20,5.00735931 20,6.25 L20,19.75 C20,20.9926407 18.9926407,22 17.75,22 L6.25,22 C5.00735931,22 4,20.9926407 4,19.75 L4,6.25 C4,5.00735931 5.00735931,4 6.25,4 L8.01379413,3.99944035 C8.00733496,4.05773764 8.00310309,4.11670658 8.00118552,4.17626017 L8,4.25 C8,3.00735931 9.00735931,2 10.25,2 L13.75,2 Z M13.75,6.5 L10.25,6.5 C9.45594921,6.5 8.75796956,6.08867052 8.357512,5.4674625 L8.37902077,5.50019943 L8.37902077,5.50019943 L6.25,5.5 C5.83578644,5.5 5.5,5.83578644 5.5,6.25 L5.5,19.75 C5.5,20.1642136 5.83578644,20.5 6.25,20.5 L17.75,20.5 C18.1642136,20.5 18.5,20.1642136 18.5,19.75 L18.5,6.25 C18.5,5.83578644 18.1642136,5.5 17.75,5.5 L15.6209792,5.50019943 L15.642488,5.4674625 C15.2420304,6.08867052 14.5440508,6.5 13.75,6.5 Z M13.75,3.5 L10.25,3.5 C9.83578644,3.5 9.5,3.83578644 9.5,4.25 C9.5,4.66421356 9.83578644,5 10.25,5 L13.75,5 C14.1642136,5 14.5,4.66421356 14.5,4.25 C14.5,3.83578644 14.1642136,3.5 13.75,3.5 Z" />
+            </Button>
+            <Button Name="ClearButton" Command="{Binding $parent[TextBox].Clear}">
+              <PathIcon Width="14"
+                        Height="14"
+                        Data="M3.52499419,3.71761187 L3.61611652,3.61611652 C4.0717282,3.16050485 4.79154862,3.13013074 5.28238813,3.52499419 L5.38388348,3.61611652 L14,12.233 L22.6161165,3.61611652 C23.1042719,3.12796116 23.8957281,3.12796116 24.3838835,3.61611652 C24.8720388,4.10427189 24.8720388,4.89572811 24.3838835,5.38388348 L15.767,14 L24.3838835,22.6161165 C24.8394952,23.0717282 24.8698693,23.7915486 24.4750058,24.2823881 L24.3838835,24.3838835 C23.9282718,24.8394952 23.2084514,24.8698693 22.7176119,24.4750058 L22.6161165,24.3838835 L14,15.767 L5.38388348,24.3838835 C4.89572811,24.8720388 4.10427189,24.8720388 3.61611652,24.3838835 C3.12796116,23.8957281 3.12796116,23.1042719 3.61611652,22.6161165 L12.233,14 L3.61611652,5.38388348 C3.16050485,4.9282718 3.13013074,4.20845138 3.52499419,3.71761187 L3.61611652,3.61611652 L3.52499419,3.71761187 Z" />
+            </Button>
+          </StackPanel>
+            <Border Classes="context-target"
+                    Padding="4, 20">
+              <Border.ContextFlyout>
+                <Flyout>
+                  <TextBlock>Hello world</TextBlock>
+                </Flyout>
+              </Border.ContextFlyout>
+              <TextBlock>Inner context flyout</TextBlock>
+            </Border>
+          </StackPanel>
+        </Flyout>
+      </TextBox.ContextFlyout>
+    </TextBox>
+  </StackPanel>
+</UserControl>
diff --git a/samples/ControlCatalog/Pages/ContextFlyoutPage.xaml.cs b/samples/ControlCatalog/Pages/ContextFlyoutPage.xaml.cs
new file mode 100644
index 0000000000..10f9ee1de8
--- /dev/null
+++ b/samples/ControlCatalog/Pages/ContextFlyoutPage.xaml.cs
@@ -0,0 +1,91 @@
+using Avalonia;
+using Avalonia.Controls;
+using Avalonia.Markup.Xaml;
+using ControlCatalog.ViewModels;
+using Avalonia.Interactivity;
+using System;
+using System.ComponentModel;
+
+namespace ControlCatalog.Pages
+{
+    public class ContextFlyoutPage : UserControl
+    {
+        private TextBox _textBox;
+
+        public ContextFlyoutPage()
+        {
+            InitializeComponent();
+
+            DataContext = new ContextPageViewModel();
+
+            _textBox = this.FindControl<TextBox>("TextBox");
+
+            var cutButton = this.FindControl<Button>("CutButton");
+            cutButton.Click += CloseFlyout;
+
+            var copyButton = this.FindControl<Button>("CopyButton");
+            copyButton.Click += CloseFlyout;
+
+            var pasteButton = this.FindControl<Button>("PasteButton");
+            pasteButton.Click += CloseFlyout;
+
+            var clearButton = this.FindControl<Button>("ClearButton");
+            clearButton.Click += CloseFlyout;
+
+            var customContextRequestedBorder = this.FindControl<Border>("CustomContextRequestedBorder");
+            customContextRequestedBorder.AddHandler(ContextRequestedEvent, CustomContextRequested, RoutingStrategies.Tunnel);
+
+            var cancellableContextBorder = this.FindControl<Border>("CancellableContextBorder");
+            cancellableContextBorder.ContextFlyout!.Closing += ContextFlyoutPage_Closing;
+            cancellableContextBorder.ContextFlyout!.Opening += ContextFlyoutPage_Opening;
+        }
+
+        private ContextPageViewModel _model;
+        protected override void OnDataContextChanged(EventArgs e)
+        {
+            if (_model != null)
+                _model.View = null;
+            _model = DataContext as ContextPageViewModel;
+            if (_model != null)
+                _model.View = this;
+
+            base.OnDataContextChanged(e);
+        }
+
+        private void ContextFlyoutPage_Closing(object sender, CancelEventArgs e)
+        {
+            var cancelCloseCheckBox = this.FindControl<CheckBox>("CancelCloseCheckBox");
+            e.Cancel = cancelCloseCheckBox.IsChecked ?? false;
+        }
+
+        private void ContextFlyoutPage_Opening(object sender, EventArgs e)
+        {
+            if (e is CancelEventArgs cancelArgs)
+            {
+                var cancelCloseCheckBox = this.FindControl<CheckBox>("CancelOpenCheckBox");
+                cancelArgs.Cancel = cancelCloseCheckBox.IsChecked ?? false;
+            }
+        }
+
+        private void CloseFlyout(object sender, RoutedEventArgs e)
+        {
+            _textBox.ContextFlyout.Hide();
+        }
+
+        public void CustomContextRequested(object sender, ContextRequestedEventArgs e)
+        {
+            var border = (Border)sender;
+            var textBlock = (TextBlock)border.Child;
+
+            textBlock.Text = e.TryGetPosition(border, out var point)
+                ? $"Context was requested with pointer at: {point.X:N0}, {point.Y:N0}"
+                : "Context was requested without pointer";
+            e.Handled = true;
+        }
+
+        private void InitializeComponent()
+        {
+            AvaloniaXamlLoader.Load(this);
+        }
+    }
+}
diff --git a/samples/ControlCatalog/Pages/ContextMenuPage.xaml b/samples/ControlCatalog/Pages/ContextMenuPage.xaml
index 25f305151d..7e564efafc 100644
--- a/samples/ControlCatalog/Pages/ContextMenuPage.xaml
+++ b/samples/ControlCatalog/Pages/ContextMenuPage.xaml
@@ -1,58 +1,88 @@
-<UserControl xmlns="https://github.com/avaloniaui"
-             xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
-             x:Class="ControlCatalog.Pages.ContextMenuPage">
-    <StackPanel Orientation="Vertical" Spacing="4">
-        <TextBlock Classes="h1">Context Menu</TextBlock>
-        <TextBlock Classes="h2">A right click menu that can be applied to any control.</TextBlock>
+<UserControl x:Class="ControlCatalog.Pages.ContextMenuPage"
+             xmlns="https://github.com/avaloniaui"
+             xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml">
+  <StackPanel Orientation="Vertical" Spacing="4">
+    <TextBlock Classes="h1">Context Menu</TextBlock>
+    <TextBlock Classes="h2">A right click menu that can be applied to any control.</TextBlock>
 
-        <StackPanel Orientation="Horizontal"
-              Margin="0,16,0,0"
-              HorizontalAlignment="Center"
-              Spacing="16">
-            <Border Background="{DynamicResource SystemAccentColor}"
-                    Margin="16"
-                    Padding="48,48,48,48">
-                <Border.ContextMenu>
-                    <ContextMenu>
-                        <MenuItem Header="Standard _Menu Item" InputGesture="Ctrl+A" />
-                        <MenuItem Header="_Disabled Menu Item" IsEnabled="False" InputGesture="Ctrl+D" />
-                        <Separator/>
-                        <MenuItem Header="Menu with _Submenu">
-                            <MenuItem Header="Submenu _1"/>
-                            <MenuItem Header="Submenu _2"/>
-                        </MenuItem>
-                        <MenuItem Header="Menu Item with _Icon" InputGesture="Ctrl+Shift+B">
-                            <MenuItem.Icon>
-                                <Image Source="/Assets/github_icon.png"/>
-                            </MenuItem.Icon>
-                        </MenuItem>
-                        <MenuItem Header="Menu Item with _Checkbox">
-                            <MenuItem.Icon>
-                                <CheckBox BorderThickness="0" IsHitTestVisible="False" IsChecked="True"/>
-                            </MenuItem.Icon>
-                        </MenuItem>
-                        <MenuItem Header="Menu Item that won't close on click" StaysOpenOnClick="True" />
-                    </ContextMenu>
-                </Border.ContextMenu>
-                <TextBlock Text="Defined in XAML"/>
-            </Border>
-            <Border Background="{DynamicResource SystemAccentColor}"
-                    Margin="16"
-                    Padding="48,48,48,48">
-                <Border.ContextMenu>
-                    <ContextMenu Items="{Binding MenuItems}">
-                        <ContextMenu.Styles>
-                            <Style Selector="MenuItem">
-                                <Setter Property="Header" Value="{Binding Header}"/>
-                                <Setter Property="Items" Value="{Binding Items}"/>
-                                <Setter Property="Command" Value="{Binding Command}"/>
-                                <Setter Property="CommandParameter" Value="{Binding CommandParameter}"/>
-                            </Style>
-                        </ContextMenu.Styles>
-                    </ContextMenu>
-                </Border.ContextMenu>
-                <TextBlock Text="Dynamically Generated"/>
-            </Border>
+    <UniformGrid HorizontalAlignment="Center" Rows="2">
+      <UniformGrid.Styles>
+        <Style Selector="UniformGrid > Border">
+          <Setter Property="Padding" Value="48,20" />
+          <Setter Property="Margin" Value="8" />
+          <Setter Property="Focusable" Value="True" />
+          <Setter Property="Background" Value="{DynamicResource SystemAccentColor}" />
+        </Style>
+        <Style Selector="UniformGrid > Border > :is(Control)">
+          <Setter Property="VerticalAlignment" Value="Center" />
+        </Style>
+      </UniformGrid.Styles>
+      <Border>
+        <Border.ContextMenu>
+          <ContextMenu>
+            <MenuItem Header="Standard _Menu Item" InputGesture="Ctrl+A" />
+            <MenuItem Header="_Disabled Menu Item"
+                      InputGesture="Ctrl+D"
+                      IsEnabled="False" />
+            <Separator />
+            <MenuItem Header="Menu with _Submenu">
+              <MenuItem Header="Submenu _1" />
+              <MenuItem Header="Submenu _2" />
+            </MenuItem>
+            <MenuItem Header="Menu Item with _Icon" InputGesture="Ctrl+Shift+B">
+              <MenuItem.Icon>
+                <Image Source="/Assets/github_icon.png" />
+              </MenuItem.Icon>
+            </MenuItem>
+            <MenuItem Header="Menu Item with _Checkbox">
+              <MenuItem.Icon>
+                <CheckBox BorderThickness="0"
+                          IsChecked="True"
+                          IsHitTestVisible="False" />
+              </MenuItem.Icon>
+            </MenuItem>
+            <MenuItem Header="Menu Item that won't close on click" StaysOpenOnClick="True" />
+          </ContextMenu>
+        </Border.ContextMenu>
+        <TextBlock Text="Defined in XAML" />
+      </Border>
+      <Border>
+        <Border.Styles>
+          <Style Selector="ContextMenu MenuItem">
+            <Setter Property="Header" Value="{Binding Header}"/>
+            <Setter Property="Items" Value="{Binding Items}"/>
+            <Setter Property="Command" Value="{Binding Command}"/>
+            <Setter Property="CommandParameter" Value="{Binding CommandParameter}"/>
+          </Style>
+        </Border.Styles>
+        <Border.ContextMenu>
+          <ContextMenu Items="{Binding MenuItems}" />
+        </Border.ContextMenu>
+        <TextBlock Text="Dynamically Generated"/>
+      </Border>
+      <Border x:Name="CustomContextRequestedBorder">
+        <Border.ContextMenu>
+          <ContextMenu>
+            <MenuItem Header="Should never be visible" />
+          </ContextMenu>
+        </Border.ContextMenu>
+        <TextBlock Text="Custom ContextRequested handler" TextWrapping="Wrap" />
+      </Border>
+      <Border x:Name="CancellableContextBorder">
+        <Border.ContextMenu>
+          <ContextMenu>
+            <MenuItem>
+              <MenuItem.Header>
+                <CheckBox x:Name="CancelCloseCheckBox" Content="Cancel close" />
+              </MenuItem.Header>
+            </MenuItem>
+          </ContextMenu>
+        </Border.ContextMenu>
+        <StackPanel>
+          <TextBlock Text="Cancellable" />
+          <CheckBox x:Name="CancelOpenCheckBox" Content="Cancel open" />
         </StackPanel>
-    </StackPanel>
+      </Border>
+    </UniformGrid>
+  </StackPanel>
 </UserControl>
diff --git a/samples/ControlCatalog/Pages/ContextMenuPage.xaml.cs b/samples/ControlCatalog/Pages/ContextMenuPage.xaml.cs
index f861bfab33..da016e9a75 100644
--- a/samples/ControlCatalog/Pages/ContextMenuPage.xaml.cs
+++ b/samples/ControlCatalog/Pages/ContextMenuPage.xaml.cs
@@ -1,5 +1,8 @@
 using System;
+using System.ComponentModel;
+
 using Avalonia.Controls;
+using Avalonia.Interactivity;
 using Avalonia.Markup.Xaml;
 using ControlCatalog.ViewModels;
 
@@ -10,21 +13,54 @@ namespace ControlCatalog.Pages
         public ContextMenuPage()
         {
             this.InitializeComponent();
-            DataContext = new ContextMenuPageViewModel();
+            DataContext = new ContextPageViewModel();
+
+            var customContextRequestedBorder = this.FindControl<Border>("CustomContextRequestedBorder");
+            customContextRequestedBorder.AddHandler(ContextRequestedEvent, CustomContextRequested, RoutingStrategies.Tunnel);
+
+            var cancellableContextBorder = this.FindControl<Border>("CancellableContextBorder");
+            cancellableContextBorder.ContextMenu!.ContextMenuClosing += ContextFlyoutPage_Closing;
+            cancellableContextBorder.ContextMenu!.ContextMenuOpening += ContextFlyoutPage_Opening;
         }
 
-        private ContextMenuPageViewModel _model;
+        private ContextPageViewModel _model;
         protected override void OnDataContextChanged(EventArgs e)
         {
             if (_model != null)
                 _model.View = null;
-            _model  = DataContext as ContextMenuPageViewModel;
+            _model  = DataContext as ContextPageViewModel;
             if (_model != null)
                 _model.View = this;
 
             base.OnDataContextChanged(e);
         }
 
+        private void ContextFlyoutPage_Closing(object sender, CancelEventArgs e)
+        {
+            var cancelCloseCheckBox = this.FindControl<CheckBox>("CancelCloseCheckBox");
+            e.Cancel = cancelCloseCheckBox.IsChecked ?? false;
+        }
+
+        private void ContextFlyoutPage_Opening(object sender, EventArgs e)
+        {
+            if (e is CancelEventArgs cancelArgs)
+            {
+                var cancelCloseCheckBox = this.FindControl<CheckBox>("CancelOpenCheckBox");
+                cancelArgs.Cancel = cancelCloseCheckBox.IsChecked ?? false;
+            }
+        }
+
+        public void CustomContextRequested(object sender, ContextRequestedEventArgs e)
+        {
+            var border = (Border)sender;
+            var textBlock = (TextBlock)border.Child;
+
+            textBlock.Text = e.TryGetPosition(border, out var point)
+                ? $"Context was requested with pointer at: {point.X:N0}, {point.Y:N0}"
+                : "Context was requested without pointer";
+            e.Handled = true;
+        }
+
         private void InitializeComponent()
         {
             AvaloniaXamlLoader.Load(this);
diff --git a/samples/ControlCatalog/Pages/DataGridPage.xaml b/samples/ControlCatalog/Pages/DataGridPage.xaml
index 323eaa3463..820c1324e3 100644
--- a/samples/ControlCatalog/Pages/DataGridPage.xaml
+++ b/samples/ControlCatalog/Pages/DataGridPage.xaml
@@ -23,16 +23,21 @@
     </StackPanel>
     <TabControl Grid.Row="2">
       <TabItem Header="DataGrid">
-        <DataGrid Name="dataGrid1" Margin="12" CanUserResizeColumns="True" CanUserReorderColumns="True" CanUserSortColumns="True" HeadersVisibility="All">
-          <DataGrid.Columns>
-            <DataGridTextColumn Header="Country" Binding="{Binding Name}" Width="6*" />
-            <!-- CompiledBinding example of usage. -->
-            <DataGridTextColumn Header="Region" Binding="{CompiledBinding Region}" Width="4*" x:DataType="local:Country" />
-            <DataGridTextColumn Header="Population" Binding="{Binding Population}" Width="3*" />
-            <DataGridTextColumn Header="Area" Binding="{Binding Area}" Width="3*" />
-            <DataGridTextColumn Header="GDP" Binding="{Binding GDP}" Width="3*" CellStyleClasses="gdp" />
-          </DataGrid.Columns>
-        </DataGrid>
+        <DockPanel>
+          <CheckBox x:Name="ShowGDP"  IsChecked="True"  Content="Toggle GDP Column Visibility"
+                    DockPanel.Dock="Top"/>
+          <DataGrid Name="dataGrid1" Margin="12" CanUserResizeColumns="True" CanUserReorderColumns="True" CanUserSortColumns="True" HeadersVisibility="All">
+            <DataGrid.Columns>
+              <DataGridTextColumn Header="Country" Binding="{Binding Name}" Width="6*" />
+              <!-- CompiledBinding example of usage. -->
+              <DataGridTextColumn Header="Region" Binding="{CompiledBinding Region}" Width="4*" x:DataType="local:Country" />
+              <DataGridTextColumn Header="Population" Binding="{Binding Population}" Width="3*" />
+              <DataGridTextColumn Header="Area" Binding="{Binding Area}" Width="3*" />
+              <DataGridTextColumn Header="GDP" Binding="{Binding GDP}" Width="3*" CellStyleClasses="gdp"
+                                  IsVisible="{Binding #ShowGDP.IsChecked}"/>
+            </DataGrid.Columns>
+          </DataGrid>
+        </DockPanel>
       </TabItem>
       <TabItem Header="Grouping">
         <DataGrid Name="dataGridGrouping" Margin="12">
diff --git a/samples/ControlCatalog/ViewModels/ContextFlyoutPageViewModel.cs b/samples/ControlCatalog/ViewModels/ContextFlyoutPageViewModel.cs
deleted file mode 100644
index 8e7fc442f6..0000000000
--- a/samples/ControlCatalog/ViewModels/ContextFlyoutPageViewModel.cs
+++ /dev/null
@@ -1,78 +0,0 @@
-using System.Collections.Generic;
-using System.Reactive;
-using System.Threading.Tasks;
-using Avalonia.Controls;
-using Avalonia.VisualTree;
-using MiniMvvm;
-
-namespace ControlCatalog.ViewModels
-{
-    public class ContextFlyoutPageViewModel
-    {
-        public Control View { get; set; }
-        public ContextFlyoutPageViewModel()
-        {
-            OpenCommand = MiniCommand.CreateFromTask(Open);
-            SaveCommand = MiniCommand.Create(Save);
-            OpenRecentCommand = MiniCommand.Create<string>(OpenRecent);
-
-            MenuItems = new[]
-            {
-                new MenuItemViewModel { Header = "_Open...", Command = OpenCommand },
-                new MenuItemViewModel { Header = "Save", Command = SaveCommand },
-                new MenuItemViewModel { Header = "-" },
-                new MenuItemViewModel
-                {
-                    Header = "Recent",
-                    Items = new[]
-                    {
-                        new MenuItemViewModel
-                        {
-                            Header = "File1.txt",
-                            Command = OpenRecentCommand,
-                            CommandParameter = @"c:\foo\File1.txt"
-                        },
-                        new MenuItemViewModel
-                        {
-                            Header = "File2.txt",
-                            Command = OpenRecentCommand,
-                            CommandParameter = @"c:\foo\File2.txt"
-                        },
-                    }
-                },
-            };
-        }
-
-        public IReadOnlyList<MenuItemViewModel> MenuItems { get; set; }
-        public MiniCommand OpenCommand { get; }
-        public MiniCommand SaveCommand { get; }
-        public MiniCommand OpenRecentCommand { get; }
-
-        public async Task Open()
-        {
-            var window = View?.GetVisualRoot() as Window;
-            if (window == null)
-                return;
-            var dialog = new OpenFileDialog();
-            var result = await dialog.ShowAsync(window);
-
-            if (result != null)
-            {
-                foreach (var path in result)
-                {
-                    System.Diagnostics.Debug.WriteLine($"Opened: {path}");
-                }
-            }
-        }
-
-        public void Save()
-        {
-            System.Diagnostics.Debug.WriteLine("Save");
-        }
-
-        public void OpenRecent(string path)
-        {
-            System.Diagnostics.Debug.WriteLine($"Open recent: {path}");
-        }
-    }
-}
diff --git a/samples/ControlCatalog/ViewModels/ContextMenuPageViewModel.cs b/samples/ControlCatalog/ViewModels/ContextPageViewModel.cs
similarity index 96%
rename from samples/ControlCatalog/ViewModels/ContextMenuPageViewModel.cs
rename to samples/ControlCatalog/ViewModels/ContextPageViewModel.cs
index 3f5d0cd93c..b46ffeb007 100644
--- a/samples/ControlCatalog/ViewModels/ContextMenuPageViewModel.cs
+++ b/samples/ControlCatalog/ViewModels/ContextPageViewModel.cs
@@ -7,10 +7,10 @@ using MiniMvvm;
 
 namespace ControlCatalog.ViewModels
 {
-    public class ContextMenuPageViewModel
+    public class ContextPageViewModel
     {
         public Control View { get; set; }
-        public ContextMenuPageViewModel()
+        public ContextPageViewModel()
         {
             OpenCommand = MiniCommand.CreateFromTask(Open);
             SaveCommand = MiniCommand.Create(Save);
diff --git a/src/Avalonia.Controls.DataGrid/DataGridColumn.cs b/src/Avalonia.Controls.DataGrid/DataGridColumn.cs
index 9141fb2463..5c09bab678 100644
--- a/src/Avalonia.Controls.DataGrid/DataGridColumn.cs
+++ b/src/Avalonia.Controls.DataGrid/DataGridColumn.cs
@@ -27,7 +27,6 @@ namespace Avalonia.Controls
         private double? _minWidth;
         private bool _settingWidthInternally;
         private int _displayIndexWithFiller;
-        private bool _isVisible;
         private object _header;
         private DataGridColumnHeader _headerCell;
         private IControl _editingElement;
@@ -40,7 +39,6 @@ namespace Avalonia.Controls
         /// </summary>
         protected internal DataGridColumn()
         {
-            _isVisible = true;
             _displayIndexWithFiller = -1;
             IsInitialDesiredWidthDetermined = false;
             InheritsWidth = true;
@@ -174,32 +172,42 @@ namespace Avalonia.Controls
             get => _editBinding;
         }
 
+
+        /// <summary>
+        /// Defines the <see cref="IsVisible"/> property.
+        /// </summary>
+        public static StyledProperty<bool> IsVisibleProperty =
+             Control.IsVisibleProperty.AddOwner<DataGridColumn>();
+
         /// <summary>
         /// Determines whether or not this column is visible.
         /// </summary>
         public bool IsVisible
         {
-            get
-            {
-                return _isVisible;
-            }
-            set
-            {
-                if (value != IsVisible)
-                {
-                    OwningGrid?.OnColumnVisibleStateChanging(this);
-                    _isVisible = value;
+            get => GetValue(IsVisibleProperty);
+            set => SetValue(IsVisibleProperty, value);
+        }
 
-                    if (_headerCell != null)
-                    {
-                        _headerCell.IsVisible = value;
-                    }
+        protected override void OnPropertyChanged<T>(AvaloniaPropertyChangedEventArgs<T> change)
+        {
+            base.OnPropertyChanged(change);
 
-                    OwningGrid?.OnColumnVisibleStateChanged(this);
+            if (change.Property == IsVisibleProperty)
+            {
+                OwningGrid?.OnColumnVisibleStateChanging(this);
+                var isVisible = (change as AvaloniaPropertyChangedEventArgs<bool>).NewValue.Value;
+
+                if (_headerCell != null)
+                {
+                    _headerCell.IsVisible = isVisible;
                 }
+
+                OwningGrid?.OnColumnVisibleStateChanged(this);
+                NotifyPropertyChanged(change.Property.Name);
             }
         }
 
+
         /// <summary>
         /// Actual visible width after Width, MinWidth, and MaxWidth setting at the Column level and DataGrid level
         /// have been taken into account
diff --git a/src/Avalonia.Controls.DataGrid/Themes/Fluent.xaml b/src/Avalonia.Controls.DataGrid/Themes/Fluent.xaml
index 0c4f8249ce..f2dbf42196 100644
--- a/src/Avalonia.Controls.DataGrid/Themes/Fluent.xaml
+++ b/src/Avalonia.Controls.DataGrid/Themes/Fluent.xaml
@@ -6,8 +6,8 @@
     <x:Double x:Key="ListAccentLowOpacity">0.6</x:Double>
     <x:Double x:Key="ListAccentMediumOpacity">0.8</x:Double>
 
-    <StreamGeometry x:Key="DataGridSortIconAscendingPath">M1875 1011l-787 787v-1798h-128v1798l-787 -787l-90 90l941 941l941 -941z</StreamGeometry>
-    <StreamGeometry x:Key="DataGridSortIconDescendingPath">M1965 947l-941 -941l-941 941l90 90l787 -787v1798h128v-1798l787 787z</StreamGeometry>
+    <StreamGeometry x:Key="DataGridSortIconDescendingPath">M1875 1011l-787 787v-1798h-128v1798l-787 -787l-90 90l941 941l941 -941z</StreamGeometry>
+    <StreamGeometry x:Key="DataGridSortIconAscendingPath">M1965 947l-941 -941l-941 941l90 90l787 -787v1798h128v-1798l787 787z</StreamGeometry>
     <StreamGeometry x:Key="DataGridRowGroupHeaderIconClosedPath">M515 93l930 931l-930 931l90 90l1022 -1021l-1022 -1021z</StreamGeometry>
     <StreamGeometry x:Key="DataGridRowGroupHeaderIconOpenedPath">M1939 1581l90 -90l-1005 -1005l-1005 1005l90 90l915 -915z</StreamGeometry>
 
diff --git a/src/Avalonia.Controls/ApiCompatBaseline.txt b/src/Avalonia.Controls/ApiCompatBaseline.txt
index bb133900d9..ea62a8d843 100644
--- a/src/Avalonia.Controls/ApiCompatBaseline.txt
+++ b/src/Avalonia.Controls/ApiCompatBaseline.txt
@@ -30,6 +30,9 @@ MembersMustExist : Member 'public System.Double Avalonia.Controls.NumericUpDownV
 MembersMustExist : Member 'public System.Double Avalonia.Controls.NumericUpDownValueChangedEventArgs.OldValue.get()' does not exist in the implementation but it does exist in the contract.
 MembersMustExist : Member 'public Avalonia.StyledProperty<System.Boolean> Avalonia.StyledProperty<System.Boolean> Avalonia.Controls.ScrollViewer.AllowAutoHideProperty' does not exist in the implementation but it does exist in the contract.
 MembersMustExist : Member 'public Avalonia.AvaloniaProperty<Avalonia.Media.Stretch> Avalonia.AvaloniaProperty<Avalonia.Media.Stretch> Avalonia.Controls.Viewbox.StretchProperty' does not exist in the implementation but it does exist in the contract.
+InterfacesShouldHaveSameMembers : Interface member 'public System.EventHandler<System.ComponentModel.CancelEventArgs> Avalonia.Controls.ApplicationLifetimes.IClassicDesktopStyleApplicationLifetime.ShutdownRequested' is present in the implementation but not in the contract.
+InterfacesShouldHaveSameMembers : Interface member 'public void Avalonia.Controls.ApplicationLifetimes.IClassicDesktopStyleApplicationLifetime.add_ShutdownRequested(System.EventHandler<System.ComponentModel.CancelEventArgs>)' is present in the implementation but not in the contract.
+InterfacesShouldHaveSameMembers : Interface member 'public void Avalonia.Controls.ApplicationLifetimes.IClassicDesktopStyleApplicationLifetime.remove_ShutdownRequested(System.EventHandler<System.ComponentModel.CancelEventArgs>)' is present in the implementation but not in the contract.
 MembersMustExist : Member 'public void Avalonia.Controls.Embedding.Offscreen.OffscreenTopLevelImplBase.SetCursor(Avalonia.Platform.IPlatformHandle)' does not exist in the implementation but it does exist in the contract.
 MembersMustExist : Member 'public Avalonia.AvaloniaProperty Avalonia.AvaloniaProperty Avalonia.Controls.Notifications.NotificationCard.CloseOnClickProperty' does not exist in the implementation but it does exist in the contract.
 EnumValuesMustMatch : Enum value 'Avalonia.Platform.ExtendClientAreaChromeHints Avalonia.Platform.ExtendClientAreaChromeHints.Default' is (System.Int32)2 in the implementation but (System.Int32)1 in the contract.
@@ -38,4 +41,4 @@ InterfacesShouldHaveSameMembers : Interface member 'public System.Nullable<Avalo
 InterfacesShouldHaveSameMembers : Interface member 'public void Avalonia.Platform.ITopLevelImpl.SetCursor(Avalonia.Platform.ICursorImpl)' is present in the implementation but not in the contract.
 InterfacesShouldHaveSameMembers : Interface member 'public void Avalonia.Platform.ITopLevelImpl.SetCursor(Avalonia.Platform.IPlatformHandle)' is present in the contract but not in the implementation.
 MembersMustExist : Member 'public void Avalonia.Platform.ITopLevelImpl.SetCursor(Avalonia.Platform.IPlatformHandle)' does not exist in the implementation but it does exist in the contract.
-Total Issues: 39
+Total Issues: 42
diff --git a/src/Avalonia.Controls/ApplicationLifetimes/ClassicDesktopStyleApplicationLifetime.cs b/src/Avalonia.Controls/ApplicationLifetimes/ClassicDesktopStyleApplicationLifetime.cs
index aa4342f075..79780dbd0b 100644
--- a/src/Avalonia.Controls/ApplicationLifetimes/ClassicDesktopStyleApplicationLifetime.cs
+++ b/src/Avalonia.Controls/ApplicationLifetimes/ClassicDesktopStyleApplicationLifetime.cs
@@ -1,5 +1,6 @@
 using System;
 using System.Collections.Generic;
+using System.ComponentModel;
 using System.Linq;
 using System.Threading;
 using Avalonia.Controls;
@@ -42,9 +43,13 @@ namespace Avalonia.Controls.ApplicationLifetimes
                     "Can not have multiple active ClassicDesktopStyleApplicationLifetime instances and the previously created one was not disposed");
             _activeLifetime = this;
         }
-        
+
         /// <inheritdoc/>
         public event EventHandler<ControlledApplicationLifetimeStartupEventArgs> Startup;
+
+        /// <inheritdoc/>
+        public event EventHandler<CancelEventArgs> ShutdownRequested;
+
         /// <inheritdoc/>
         public event EventHandler<ControlledApplicationLifetimeExitEventArgs> Exit;
 
@@ -111,6 +116,11 @@ namespace Avalonia.Controls.ApplicationLifetimes
                 ((IApplicationPlatformEvents)Application.Current).RaiseUrlsOpened(args);
             }
 
+            var lifetimeEvents = AvaloniaLocator.Current.GetService<IPlatformLifetimeEventsImpl>(); 
+
+            if (lifetimeEvents != null)
+                lifetimeEvents.ShutdownRequested += OnShutdownRequested;
+
             _cts = new CancellationTokenSource();
             MainWindow?.Show();
             Dispatcher.UIThread.MainLoop(_cts.Token);
@@ -123,6 +133,23 @@ namespace Avalonia.Controls.ApplicationLifetimes
             if (_activeLifetime == this)
                 _activeLifetime = null;
         }
+        
+        private void OnShutdownRequested(object sender, CancelEventArgs e)
+        {
+            ShutdownRequested?.Invoke(this, e);
+
+            if (e.Cancel)
+                return;
+
+            // When an OS shutdown request is received, try to close all non-owned windows. Windows can cancel
+            // shutdown by setting e.Cancel = true in the Closing event. Owned windows will be shutdown by their
+            // owners.
+            foreach (var w in Windows)
+                if (w.Owner is null)
+                    w.Close();
+            if (Windows.Count > 0)
+                e.Cancel = true;
+        }
     }
     
     public class ClassicDesktopStyleApplicationLifetimeOptions
diff --git a/src/Avalonia.Controls/ApplicationLifetimes/IClassicDesktopStyleApplicationLifetime.cs b/src/Avalonia.Controls/ApplicationLifetimes/IClassicDesktopStyleApplicationLifetime.cs
index 212f0b8617..ecf8a0358f 100644
--- a/src/Avalonia.Controls/ApplicationLifetimes/IClassicDesktopStyleApplicationLifetime.cs
+++ b/src/Avalonia.Controls/ApplicationLifetimes/IClassicDesktopStyleApplicationLifetime.cs
@@ -1,5 +1,6 @@
 using System;
 using System.Collections.Generic;
+using System.ComponentModel;
 
 namespace Avalonia.Controls.ApplicationLifetimes
 {
@@ -34,5 +35,16 @@ namespace Avalonia.Controls.ApplicationLifetimes
         Window MainWindow { get; set; }
         
         IReadOnlyList<Window> Windows { get; }
+
+        /// <summary>
+        /// Raised by the platform when a shutdown is requested.
+        /// </summary>
+        /// <remarks>
+        /// Raised on on OSX via the Quit menu or right-clicking on the application icon and selecting Quit. This event
+        /// provides a first-chance to cancel application shutdown; if shutdown is not canceled at this point the application
+        /// will try to close each non-owned open window, invoking the <see cref="Window.Closing"/> event on each and allowing
+        /// each window to cancel the shutdown.
+        /// </remarks>
+        event EventHandler<CancelEventArgs> ShutdownRequested;
     }
 }
diff --git a/src/Avalonia.Controls/ComboBox.cs b/src/Avalonia.Controls/ComboBox.cs
index 89cfb5fa8f..57c07916db 100644
--- a/src/Avalonia.Controls/ComboBox.cs
+++ b/src/Avalonia.Controls/ComboBox.cs
@@ -91,6 +91,7 @@ namespace Avalonia.Controls
             FocusableProperty.OverrideDefaultValue<ComboBox>(true);
             SelectedItemProperty.Changed.AddClassHandler<ComboBox>((x,e) => x.SelectedItemChanged(e));
             KeyDownEvent.AddClassHandler<ComboBox>((x, e) => x.OnKeyDown(e), Interactivity.RoutingStrategies.Tunnel);
+            IsTextSearchEnabledProperty.OverrideDefaultValue<ComboBox>(true);
         }
 
         /// <summary>
diff --git a/src/Avalonia.Controls/ContextMenu.cs b/src/Avalonia.Controls/ContextMenu.cs
index 57e4909e39..ead5b0d9f3 100644
--- a/src/Avalonia.Controls/ContextMenu.cs
+++ b/src/Avalonia.Controls/ContextMenu.cs
@@ -1,12 +1,15 @@
 using System;
 using System.Collections.Generic;
 using System.ComponentModel;
+using System.Linq;
+
 using Avalonia.Controls.Generators;
 using Avalonia.Controls.Platform;
 using Avalonia.Controls.Primitives;
 using Avalonia.Controls.Primitives.PopupPositioning;
 using Avalonia.Controls.Templates;
 using Avalonia.Input;
+using Avalonia.Input.Platform;
 using Avalonia.Interactivity;
 using Avalonia.Layout;
 using Avalonia.Styling;
@@ -220,7 +223,8 @@ namespace Avalonia.Controls
 
             if (e.OldValue is ContextMenu oldMenu)
             {
-                control.PointerReleased -= ControlPointerReleased;
+                control.ContextRequested -= ControlContextRequested;
+                control.DetachedFromVisualTree -= ControlDetachedFromVisualTree;
                 oldMenu._attachedControls?.Remove(control);
                 ((ISetLogicalParent?)oldMenu._popup)?.SetParent(null);
             }
@@ -229,7 +233,8 @@ namespace Avalonia.Controls
             {
                 newMenu._attachedControls ??= new List<Control>();
                 newMenu._attachedControls.Add(control);
-                control.PointerReleased += ControlPointerReleased;
+                control.ContextRequested += ControlContextRequested;
+                control.DetachedFromVisualTree += ControlDetachedFromVisualTree;
             }
         }
 
@@ -269,7 +274,7 @@ namespace Avalonia.Controls
             }
 
             control ??= _attachedControls![0];
-            Open(control, PlacementTarget ?? control);
+            Open(control, PlacementTarget ?? control, false);
         }
 
         /// <summary>
@@ -304,7 +309,7 @@ namespace Avalonia.Controls
             return new MenuItemContainerGenerator(this);
         }
 
-        private void Open(Control control, Control placementTarget)
+        private void Open(Control control, Control placementTarget, bool requestedByPointer)
         {
             if (IsOpen)
             {
@@ -329,6 +334,8 @@ namespace Avalonia.Controls
 
                 _popup.Opened += PopupOpened;
                 _popup.Closed += PopupClosed;
+                _popup.Closing += PopupClosing;
+                _popup.KeyUp += PopupKeyUp;
             }
 
             if (_popup.Parent != control)
@@ -337,6 +344,10 @@ namespace Avalonia.Controls
                 ((ISetLogicalParent)_popup).SetParent(control);
             }
 
+            _popup.PlacementMode = !requestedByPointer && PlacementMode == PlacementMode.Pointer
+                ? PlacementMode.Bottom
+                : PlacementMode;
+
             _popup.PlacementTarget = placementTarget;
             _popup.Child = this;
             IsOpen = true;
@@ -355,6 +366,11 @@ namespace Avalonia.Controls
             Focus();
         }
 
+        private void PopupClosing(object sender, CancelEventArgs e)
+        {
+            e.Cancel = CancelClosing();
+        }
+
         private void PopupClosed(object sender, EventArgs e)
         {
             foreach (var i in LogicalChildren)
@@ -383,30 +399,43 @@ namespace Avalonia.Controls
             });
         }
 
-        private static void ControlPointerReleased(object sender, PointerReleasedEventArgs e)
+        private void PopupKeyUp(object sender, KeyEventArgs e)
         {
-            var control = (Control)sender;
-            var contextMenu = control.ContextMenu;
-
-            if (control.ContextMenu.IsOpen)
+            if (IsOpen)
             {
-                if (contextMenu.CancelClosing())
-                    return;
+                var keymap = AvaloniaLocator.Current.GetService<PlatformHotkeyConfiguration>();
 
-                control.ContextMenu.Close();
-                e.Handled = true;
+                if (keymap.OpenContextMenu.Any(k => k.Matches(e))
+                    && !CancelClosing())
+                {
+                    Close();
+                    e.Handled = true;
+                }
             }
+        }
 
-            if (e.InitialPressMouseButton == MouseButton.Right)
+        private static void ControlContextRequested(object sender, ContextRequestedEventArgs e)
+        {
+            if (sender is Control control
+                && control.ContextMenu is ContextMenu contextMenu
+                && !e.Handled
+                && !contextMenu.CancelOpening())
             {
-                if (contextMenu.CancelOpening())
-                    return;
-
-                contextMenu.Open(control, e.Source as Control ?? control);
+                var requestedByPointer = e.TryGetPosition(null, out _);
+                contextMenu.Open(control, e.Source as Control ?? control, requestedByPointer);
                 e.Handled = true;
             }
         }
 
+        private static void ControlDetachedFromVisualTree(object sender, VisualTreeAttachmentEventArgs e)
+        {
+            if (sender is Control control
+                && control.ContextMenu is ContextMenu contextMenu)
+            {
+                contextMenu.Close();
+            }
+        }
+
         private bool CancelClosing()
         {
             var eventArgs = new CancelEventArgs();
diff --git a/src/Avalonia.Controls/ContextRequestedEventArgs.cs b/src/Avalonia.Controls/ContextRequestedEventArgs.cs
new file mode 100644
index 0000000000..8dc798245c
--- /dev/null
+++ b/src/Avalonia.Controls/ContextRequestedEventArgs.cs
@@ -0,0 +1,58 @@
+using Avalonia.Input;
+using Avalonia.Interactivity;
+
+#nullable enable
+
+namespace Avalonia.Controls
+{
+    /// <summary>
+    /// Provides event data for the ContextRequested event.
+    /// </summary>
+    public class ContextRequestedEventArgs : RoutedEventArgs
+    {
+        private readonly PointerEventArgs? _pointerEventArgs;
+
+        /// <summary>
+        /// Initializes a new instance of the ContextRequestedEventArgs class.
+        /// </summary>
+        public ContextRequestedEventArgs()
+            : base(Control.ContextRequestedEvent)
+        {
+
+        }
+
+        /// <inheritdoc cref="ContextRequestedEventArgs()" />
+        public ContextRequestedEventArgs(PointerEventArgs pointerEventArgs)
+            : this()
+        {
+            _pointerEventArgs = pointerEventArgs;
+        }
+
+        /// <summary>
+        /// Gets the x- and y-coordinates of the pointer position, optionally evaluated against a coordinate origin of a supplied <see cref="Control"/>.
+        /// </summary>
+        /// <param name="relativeTo">
+        /// Any <see cref="Control"/>-derived object that is connected to the same object tree.
+        /// To specify the object relative to the overall coordinate system, use a relativeTo  value of null.
+        /// </param>
+        /// <param name="point">
+        /// A <see cref="Point"/> that represents the current x- and y-coordinates of the mouse pointer position.
+        /// If null was passed as relativeTo, this coordinate is for the overall window.
+        /// If a relativeTo value other than null was passed, this coordinate is relative to the object referenced by relativeTo.
+        /// </param>
+        /// <returns>
+        /// true if the context request was initiated by a pointer device; otherwise, false.
+        /// </returns>
+        public bool TryGetPosition(Control? relativeTo, out Point point)
+        {
+            if (_pointerEventArgs is null)
+            {
+                point = default;
+                return false;
+            }
+
+            point = _pointerEventArgs.GetPosition(relativeTo);
+            return true;
+        }
+    }
+}
diff --git a/src/Avalonia.Controls/Control.cs b/src/Avalonia.Controls/Control.cs
index a7ec7cc5d2..fe731b9d4b 100644
--- a/src/Avalonia.Controls/Control.cs
+++ b/src/Avalonia.Controls/Control.cs
@@ -3,6 +3,7 @@ using System.ComponentModel;
 using Avalonia.Controls.Primitives;
 using Avalonia.Controls.Templates;
 using Avalonia.Input;
+using Avalonia.Input.Platform;
 using Avalonia.Interactivity;
 using Avalonia.Rendering;
 using Avalonia.Styling;
@@ -19,6 +20,7 @@ namespace Avalonia.Controls
     /// The control class extends <see cref="InputElement"/> and adds the following features:
     ///
     /// - A <see cref="Tag"/> property to allow user-defined data to be attached to the control.
+    /// - <see cref="ContextRequestedEvent"/> and other context menu related members.
     /// </remarks>
     public class Control : InputElement, IControl, INamed, IVisualBrushInitialize, ISetterValue
     {
@@ -52,6 +54,13 @@ namespace Avalonia.Controls
         public static readonly RoutedEvent<RequestBringIntoViewEventArgs> RequestBringIntoViewEvent =
             RoutedEvent.Register<Control, RequestBringIntoViewEventArgs>("RequestBringIntoView", RoutingStrategies.Bubble);
 
+        /// <summary>
+        /// Provides event data for the <see cref="ContextRequested"/> event.
+        /// </summary>
+        public static readonly RoutedEvent<ContextRequestedEventArgs> ContextRequestedEvent =
+            RoutedEvent.Register<Control, ContextRequestedEventArgs>(nameof(ContextRequested),
+                RoutingStrategies.Tunnel | RoutingStrategies.Bubble);
+
         private DataTemplates? _dataTemplates;
         private IControl? _focusAdorner;
 
@@ -100,6 +109,15 @@ namespace Avalonia.Controls
             set => SetValue(TagProperty, value);
         }
 
+        /// <summary>
+        /// Occurs when the user has completed a context input gesture, such as a right-click.
+        /// </summary>
+        public event EventHandler<ContextRequestedEventArgs> ContextRequested
+        {
+            add => AddHandler(ContextRequestedEvent, value);
+            remove => RemoveHandler(ContextRequestedEvent, value);
+        }
+
         public new IControl? Parent => (IControl?)base.Parent;
 
         /// <inheritdoc/>
@@ -208,5 +226,49 @@ namespace Avalonia.Controls
                 _focusAdorner = null;
             }
         }
+
+        protected override void OnPointerReleased(PointerReleasedEventArgs e)
+        {
+            base.OnPointerReleased(e);
+
+            if (e.Source == this
+                && !e.Handled
+                && e.InitialPressMouseButton == MouseButton.Right)
+            {
+                var args = new ContextRequestedEventArgs(e);
+                RaiseEvent(args);
+                e.Handled = args.Handled;
+            }
+        }
+
+        protected override void OnKeyUp(KeyEventArgs e)
+        {
+            base.OnKeyUp(e);
+
+            if (e.Source == this
+                && !e.Handled)
+            {
+                var keymap = AvaloniaLocator.Current.GetService<PlatformHotkeyConfiguration>().OpenContextMenu;
+                var matches = false;
+
+                for (var index = 0; index < keymap.Count; index++)
+                {
+                    var key = keymap[index];
+                    matches |= key.Matches(e);
+
+                    if (matches)
+                    {
+                        break;
+                    }
+                }
+
+                if (matches)
+                {
+                    var args = new ContextRequestedEventArgs();
+                    RaiseEvent(args);
+                    e.Handled = args.Handled;
+                }
+            }
+        }
     }
 }
diff --git a/src/Avalonia.Controls/Flyouts/FlyoutBase.cs b/src/Avalonia.Controls/Flyouts/FlyoutBase.cs
index e4b68c62fd..30fb2c7761 100644
--- a/src/Avalonia.Controls/Flyouts/FlyoutBase.cs
+++ b/src/Avalonia.Controls/Flyouts/FlyoutBase.cs
@@ -1,6 +1,9 @@
 using System;
 using System.ComponentModel;
+using System.Linq;
+
 using Avalonia.Input;
+using Avalonia.Input.Platform;
 using Avalonia.Input.Raw;
 using Avalonia.Layout;
 using Avalonia.Logging;
@@ -49,6 +52,7 @@ namespace Avalonia.Controls.Primitives
         public static readonly AttachedProperty<FlyoutBase?> AttachedFlyoutProperty =
             AvaloniaProperty.RegisterAttached<FlyoutBase, Control, FlyoutBase?>("AttachedFlyout", null);
 
+        private readonly Lazy<Popup> _popupLazy;
         private bool _isOpen;
         private Control? _target;
         private FlyoutShowMode _showMode = FlyoutShowMode.Standard;
@@ -56,7 +60,12 @@ namespace Avalonia.Controls.Primitives
         private PixelRect? _enlargePopupRectScreenPixelRect;
         private IDisposable? _transientDisposable;
 
-        protected Popup? Popup { get; private set; }
+        public FlyoutBase()
+        {
+            _popupLazy = new Lazy<Popup>(() => CreatePopup());
+        }
+
+        protected Popup Popup => _popupLazy.Value;
 
         /// <summary>
         /// Gets whether this Flyout is currently Open
@@ -142,22 +151,19 @@ namespace Avalonia.Controls.Primitives
             HideCore();
         }
 
-        protected virtual void HideCore(bool canCancel = true)
+        /// <returns>True, if action was handled</returns>
+        protected virtual bool HideCore(bool canCancel = true)
         {
             if (!IsOpen)
             {
-                return;
+                return false;
             }
 
             if (canCancel)
             {
-                bool cancel = false;
-
-                var closing = new CancelEventArgs();
-                Closing?.Invoke(this, closing);
-                if (cancel || closing.Cancel)
+                if (CancelClosing())
                 {
-                    return;
+                    return false;
                 }
             }
 
@@ -170,31 +176,42 @@ namespace Avalonia.Controls.Primitives
             _enlargedPopupRect = null;
             _enlargePopupRectScreenPixelRect = null;
 
+            if (Target != null)
+            {
+                Target.DetachedFromVisualTree -= PlacementTarget_DetachedFromVisualTree;
+                Target.KeyUp -= OnPlacementTargetOrPopupKeyUp;
+            }
+
             OnClosed();
+
+            return true;
         }
 
-        protected virtual void ShowAtCore(Control placementTarget, bool showAtPointer = false)
+        /// <returns>True, if action was handled</returns>
+        protected virtual bool ShowAtCore(Control placementTarget, bool showAtPointer = false)
         {
             if (placementTarget == null)
-                throw new ArgumentNullException("placementTarget cannot be null");
-
-            if (Popup == null)
             {
-                InitPopup();
+                throw new ArgumentNullException(nameof(placementTarget));
             }
 
             if (IsOpen)
             {
                 if (placementTarget == Target)
                 {
-                    return;
+                    return false;
                 }
                 else // Close before opening a new one
                 {
-                    HideCore(false);
+                    _ = HideCore(false);
                 }
             }
 
+            if (CancelOpening())
+            {
+                return false;
+            }
+
             if (Popup.Parent != null && Popup.Parent != placementTarget)
             {
                 ((ISetLogicalParent)Popup).SetParent(null);
@@ -211,11 +228,13 @@ namespace Avalonia.Controls.Primitives
                 Popup.Child = CreatePresenter();
             }
 
-            OnOpening();
             PositionPopup(showAtPointer);
-            IsOpen = Popup.IsOpen = true;            
+            IsOpen = Popup.IsOpen = true;
             OnOpened();
-                        
+
+            placementTarget.DetachedFromVisualTree += PlacementTarget_DetachedFromVisualTree;
+            placementTarget.KeyUp += OnPlacementTargetOrPopupKeyUp;
+
             if (ShowMode == FlyoutShowMode.Standard)
             {
                 // Try and focus content inside Flyout
@@ -236,6 +255,13 @@ namespace Avalonia.Controls.Primitives
             {
                 _transientDisposable = InputManager.Instance?.Process.Subscribe(HandleTransientDismiss);
             }
+
+            return true;
+        }
+
+        private void PlacementTarget_DetachedFromVisualTree(object sender, VisualTreeAttachmentEventArgs e)
+        {
+            _ = HideCore(false);
         }
 
         private void HandleTransientDismiss(RawInputEventArgs args)
@@ -254,7 +280,7 @@ namespace Avalonia.Controls.Primitives
                 {
                     // Only do this once when the Flyout opens & cache the result
                     if (Popup?.Host is PopupRoot root)
-                    { 
+                    {
                         // Get the popup root bounds and convert to screen coordinates
                         
                         var tmp = root.Bounds.Inflate(100);
@@ -294,9 +320,9 @@ namespace Avalonia.Controls.Primitives
             }
         }
 
-        protected virtual void OnOpening()
+        protected virtual void OnOpening(CancelEventArgs args)
         {
-            Opening?.Invoke(this, null);
+            Opening?.Invoke(this, args);
         }
 
         protected virtual void OnOpened()
@@ -320,14 +346,18 @@ namespace Avalonia.Controls.Primitives
         /// <returns></returns>
         protected abstract Control CreatePresenter();
 
-        private void InitPopup()
+        private Popup CreatePopup()
         {
-            Popup = new Popup();
-            Popup.WindowManagerAddShadowHint = false;
-            Popup.IsLightDismissEnabled = true;
-
-            Popup.Opened += OnPopupOpened;
-            Popup.Closed += OnPopupClosed;
+            var popup = new Popup();
+            popup.WindowManagerAddShadowHint = false;
+            popup.IsLightDismissEnabled = true;
+            popup.OverlayDismissEventPassThrough = true;
+
+            popup.Opened += OnPopupOpened;
+            popup.Closed += OnPopupClosed;
+            popup.Closing += OnPopupClosing;
+            popup.KeyUp += OnPlacementTargetOrPopupKeyUp;
+            return popup;
         }
 
         private void OnPopupOpened(object sender, EventArgs e)
@@ -335,15 +365,40 @@ namespace Avalonia.Controls.Primitives
             IsOpen = true;
         }
 
+        private void OnPopupClosing(object sender, CancelEventArgs e)
+        {
+            if (IsOpen)
+            {
+                e.Cancel = CancelClosing();
+            }
+        }
+
         private void OnPopupClosed(object sender, EventArgs e)
         {
-            HideCore();
+            HideCore(false);
+        }
+
+        // This method is handling both popup logical tree and target logical tree.
+        private void OnPlacementTargetOrPopupKeyUp(object sender, KeyEventArgs e)
+        {
+            if (!e.Handled
+                && IsOpen
+                && Target?.ContextFlyout == this)
+            {
+                var keymap = AvaloniaLocator.Current.GetService<PlatformHotkeyConfiguration>();
+
+                if (keymap.OpenContextMenu.Any(k => k.Matches(e)))
+                {
+                    e.Handled = HideCore();
+                }
+            }
         }
 
         private void PositionPopup(bool showAtPointer)
         {
             Size sz;
-            if(Popup.Child.DesiredSize == Size.Empty)
+            // Popup.Child can't be null here, it was set in ShowAtCore.
+            if (Popup.Child!.DesiredSize == Size.Empty)
             {
                 // Popup may not have been shown yet. Measure content
                 sz = LayoutHelper.MeasureChild(Popup.Child, Size.Infinity, new Thickness());
@@ -370,19 +425,19 @@ namespace Avalonia.Controls.Primitives
             switch (Placement)
             {
                 case FlyoutPlacementMode.Top: //Above & centered
-                    Popup.PlacementRect = new Rect(0, 0, trgtBnds.Width-1, 1);
+                    Popup.PlacementRect = new Rect(0, 0, trgtBnds.Width - 1, 1);
                     Popup.PlacementGravity = PopupPositioning.PopupGravity.Top;
                     Popup.PlacementAnchor = PopupPositioning.PopupAnchor.Top;
                     break;
 
                 case FlyoutPlacementMode.TopEdgeAlignedLeft:
                     Popup.PlacementRect = new Rect(0, 0, 0, 0);
-                    Popup.PlacementGravity = PopupPositioning.PopupGravity.TopRight;                    
+                    Popup.PlacementGravity = PopupPositioning.PopupGravity.TopRight;
                     break;
 
                 case FlyoutPlacementMode.TopEdgeAlignedRight:
                     Popup.PlacementRect = new Rect(trgtBnds.Width - 1, 0, 10, 1);
-                    Popup.PlacementGravity = PopupPositioning.PopupGravity.TopLeft;                    
+                    Popup.PlacementGravity = PopupPositioning.PopupGravity.TopLeft;
                     break;
 
                 case FlyoutPlacementMode.RightEdgeAlignedTop:
@@ -454,33 +509,45 @@ namespace Avalonia.Controls.Primitives
             {
                 if (args.OldValue is FlyoutBase)
                 {
-                    c.PointerReleased -= OnControlWithContextFlyoutPointerReleased;
+                    c.ContextRequested -= OnControlContextRequested;
                 }
                 if (args.NewValue is FlyoutBase)
                 {
-                    c.PointerReleased += OnControlWithContextFlyoutPointerReleased;
+                    c.ContextRequested += OnControlContextRequested;
                 }
             }
         }
 
-        private static void OnControlWithContextFlyoutPointerReleased(object sender, PointerReleasedEventArgs e)
+        private static void OnControlContextRequested(object sender, ContextRequestedEventArgs e)
         {
-            if (sender is Control c)
+            var control = (Control)sender;
+            if (!e.Handled
+                && control.ContextFlyout is FlyoutBase flyout)
             {
-                if (e.InitialPressMouseButton == MouseButton.Right &&
-                e.GetCurrentPoint(c).Properties.PointerUpdateKind == PointerUpdateKind.RightButtonReleased)
+                if (control.ContextMenu != null)
                 {
-                    if (c.ContextFlyout != null)
-                    {
-                        if (c.ContextMenu != null)
-                        {
-                            Logger.TryGet(LogEventLevel.Verbose, "FlyoutBase")?.Log(c, "ContextMenu and ContextFlyout are both set, defaulting to ContextMenu");
-                            return;
-                        }
-                        c.ContextFlyout.ShowAt(c, true);
-                    }
+                    Logger.TryGet(LogEventLevel.Verbose, "FlyoutBase")?.Log(control, "ContextMenu and ContextFlyout are both set, defaulting to ContextMenu");
+                    return;
                 }
-            }            
+
+                // We do not support absolute popup positioning yet, so we ignore "point" at this moment.
+                var triggeredByPointerInput = e.TryGetPosition(null, out _);
+                e.Handled = flyout.ShowAtCore(control, triggeredByPointerInput);
+            }
+        }
+
+        private bool CancelClosing()
+        {
+            var eventArgs = new CancelEventArgs();
+            OnClosing(eventArgs);
+            return eventArgs.Cancel;
+        }
+
+        private bool CancelOpening()
+        {
+            var eventArgs = new CancelEventArgs();
+            OnOpening(eventArgs);
+            return eventArgs.Cancel;
         }
 
         internal static void SetPresenterClasses(IControl presenter, Classes classes)
diff --git a/src/Avalonia.Controls/Flyouts/FlyoutShowMode.cs b/src/Avalonia.Controls/Flyouts/FlyoutShowMode.cs
index cb5b5f00c0..fe496619fd 100644
--- a/src/Avalonia.Controls/Flyouts/FlyoutShowMode.cs
+++ b/src/Avalonia.Controls/Flyouts/FlyoutShowMode.cs
@@ -12,7 +12,7 @@
         Standard,
 
         /// <summary>
-        /// Behavior is typical of a flyout shown proactively. The open flyout does not take focus. For a CommandBarFlyout, it opens in it's collapsed state.
+        /// Behavior is typical of a flyout shown proactively. The open flyout does not take focus.
         /// </summary>
         Transient,
 
diff --git a/src/Avalonia.Controls/Flyouts/MenuFlyoutPresenter.cs b/src/Avalonia.Controls/Flyouts/MenuFlyoutPresenter.cs
index 92f414631a..3a45c85c70 100644
--- a/src/Avalonia.Controls/Flyouts/MenuFlyoutPresenter.cs
+++ b/src/Avalonia.Controls/Flyouts/MenuFlyoutPresenter.cs
@@ -29,16 +29,8 @@ namespace Avalonia.Controls
             var host = this.FindLogicalAncestorOfType<Popup>();
             if (host != null)
             {
-                for (int i = 0; i < LogicalChildren.Count; i++)
-                {
-                    if (LogicalChildren[i] is MenuItem item)
-                    {
-                        item.IsSubMenuOpen = false;
-                    }
-                }
-
                 SelectedIndex = -1;
-                host.IsOpen = false;                
+                host.IsOpen = false;
             }
         }
 
diff --git a/src/Avalonia.Controls/Platform/IPlatformLifetimeEventsImpl.cs b/src/Avalonia.Controls/Platform/IPlatformLifetimeEventsImpl.cs
new file mode 100644
index 0000000000..8e660777e9
--- /dev/null
+++ b/src/Avalonia.Controls/Platform/IPlatformLifetimeEventsImpl.cs
@@ -0,0 +1,16 @@
+using System;
+using System.ComponentModel;
+
+namespace Avalonia.Platform
+{
+    public interface IPlatformLifetimeEventsImpl
+    {
+        /// <summary>
+        /// Raised by the platform when a shutdown is requested.
+        /// </summary>
+        /// <remarks>
+        /// Raised on on OSX via the Quit menu or right-clicking on the application icon and selecting Quit.
+        /// </remarks>
+        event EventHandler<CancelEventArgs> ShutdownRequested;
+    }
+}
diff --git a/src/Avalonia.Controls/Primitives/Popup.cs b/src/Avalonia.Controls/Primitives/Popup.cs
index b445de0472..f23a27e67a 100644
--- a/src/Avalonia.Controls/Primitives/Popup.cs
+++ b/src/Avalonia.Controls/Primitives/Popup.cs
@@ -1,4 +1,5 @@
 using System;
+using System.ComponentModel;
 using System.Linq;
 using System.Reactive.Disposables;
 using Avalonia.Controls.Presenters;
@@ -154,6 +155,8 @@ namespace Avalonia.Controls.Primitives
         /// </summary>
         public event EventHandler? Opened;
 
+        internal event EventHandler<CancelEventArgs>? Closing;
+
         public IPopupHost? Host => _openState?.PopupHost;
 
         public bool WindowManagerAddShadowHint
@@ -567,6 +570,13 @@ namespace Avalonia.Controls.Primitives
 
         private void CloseCore()
         {
+            var closingArgs = new CancelEventArgs();
+            Closing?.Invoke(this, closingArgs);
+            if (closingArgs.Cancel)
+            {
+                return;
+            }
+
             _isOpenRequested = false;
             if (_openState is null)
             {
diff --git a/src/Avalonia.Controls/Primitives/SelectingItemsControl.cs b/src/Avalonia.Controls/Primitives/SelectingItemsControl.cs
index 2fd08ef77c..336ff711c0 100644
--- a/src/Avalonia.Controls/Primitives/SelectingItemsControl.cs
+++ b/src/Avalonia.Controls/Primitives/SelectingItemsControl.cs
@@ -96,7 +96,7 @@ namespace Avalonia.Controls.Primitives
         /// Defines the <see cref="IsTextSearchEnabled"/> property.
         /// </summary>
         public static readonly StyledProperty<bool> IsTextSearchEnabledProperty =
-            AvaloniaProperty.Register<ItemsControl, bool>(nameof(IsTextSearchEnabled), true);
+            AvaloniaProperty.Register<ItemsControl, bool>(nameof(IsTextSearchEnabled), false);
 
         /// <summary>
         /// Event that should be raised by items that implement <see cref="ISelectable"/> to
diff --git a/src/Avalonia.Controls/TextBox.cs b/src/Avalonia.Controls/TextBox.cs
index ddf55808ce..91411cbd3b 100644
--- a/src/Avalonia.Controls/TextBox.cs
+++ b/src/Avalonia.Controls/TextBox.cs
@@ -1098,6 +1098,11 @@ namespace Avalonia.Controls
 
         private bool MoveVertical(int count)
         {
+            if (_presenter is null)
+            {
+                return false;
+            }
+
             var formattedText = _presenter.FormattedText;
             var lines = formattedText.GetLines().ToList();
             var caretIndex = CaretIndex;
@@ -1113,14 +1118,17 @@ namespace Avalonia.Controls
                 CaretIndex = hit.TextPosition + (hit.IsTrailing ? 1 : 0);
                 return true;
             }
-            else
-            {
-                return false;
-            }
+
+            return false;
         }
 
         private void MoveHome(bool document)
         {
+            if (_presenter is null)
+            {
+                return;
+            }
+            
             var text = Text ?? string.Empty;
             var caretIndex = CaretIndex;
 
@@ -1151,6 +1159,11 @@ namespace Avalonia.Controls
 
         private void MoveEnd(bool document)
         {
+            if (_presenter is null)
+            {
+                return;
+            }
+            
             var text = Text ?? string.Empty;
             var caretIndex = CaretIndex;
 
diff --git a/src/Avalonia.Input/Platform/PlatformHotkeyConfiguration.cs b/src/Avalonia.Input/Platform/PlatformHotkeyConfiguration.cs
index 053f894755..521f847a0a 100644
--- a/src/Avalonia.Input/Platform/PlatformHotkeyConfiguration.cs
+++ b/src/Avalonia.Input/Platform/PlatformHotkeyConfiguration.cs
@@ -1,14 +1,16 @@
 using System.Collections.Generic;
 
+#nullable enable
+
 namespace Avalonia.Input.Platform
 {
     public class PlatformHotkeyConfiguration
     {
         public PlatformHotkeyConfiguration() : this(KeyModifiers.Control)
         {
-            
+
         }
-        
+
         public PlatformHotkeyConfiguration(KeyModifiers commandModifiers,
             KeyModifiers selectionModifiers = KeyModifiers.Shift,
             KeyModifiers wholeWordTextActionModifiers = KeyModifiers.Control)
@@ -73,8 +75,12 @@ namespace Avalonia.Input.Platform
             {
                 new KeyGesture(Key.End, commandModifiers | selectionModifiers)
             };
+            OpenContextMenu = new List<KeyGesture>
+            {
+                new KeyGesture(Key.Apps)
+            };
         }
-        
+
         public KeyModifiers CommandModifiers { get; set; }
         public KeyModifiers WholeWordTextActionModifiers { get; set; }
         public KeyModifiers SelectionModifiers { get; set; }
@@ -92,7 +98,6 @@ namespace Avalonia.Input.Platform
         public List<KeyGesture> MoveCursorToTheEndOfLineWithSelection { get; set; }
         public List<KeyGesture> MoveCursorToTheStartOfDocumentWithSelection { get; set; }
         public List<KeyGesture> MoveCursorToTheEndOfDocumentWithSelection { get; set; }
-        
-        
+        public List<KeyGesture> OpenContextMenu { get; set; }
     }
 }
diff --git a/src/Avalonia.Native/AvaloniaNativeApplicationPlatform.cs b/src/Avalonia.Native/AvaloniaNativeApplicationPlatform.cs
index 9579aa93b1..77c0794d04 100644
--- a/src/Avalonia.Native/AvaloniaNativeApplicationPlatform.cs
+++ b/src/Avalonia.Native/AvaloniaNativeApplicationPlatform.cs
@@ -1,14 +1,25 @@
 using System;
+using System.ComponentModel;
 using Avalonia.Native.Interop;
 using Avalonia.Platform;
 
 namespace Avalonia.Native
 {
-    internal class AvaloniaNativeApplicationPlatform : CallbackBase, IAvnApplicationEvents
+    internal class AvaloniaNativeApplicationPlatform : CallbackBase, IAvnApplicationEvents, IPlatformLifetimeEventsImpl
     {
+        public event EventHandler<CancelEventArgs> ShutdownRequested;
+        
         void IAvnApplicationEvents.FilesOpened(IAvnStringArray urls)
         {
             ((IApplicationPlatformEvents)Application.Current).RaiseUrlsOpened(urls.ToStringArray());
         }
+
+        public int TryShutdown()
+        {
+            if (ShutdownRequested is null) return 1;
+            var e = new CancelEventArgs();
+            ShutdownRequested(this, e);
+            return (!e.Cancel).AsComBool();
+        }
     }
 }
diff --git a/src/Avalonia.Native/AvaloniaNativePlatform.cs b/src/Avalonia.Native/AvaloniaNativePlatform.cs
index 82a845ffc1..60c0b36891 100644
--- a/src/Avalonia.Native/AvaloniaNativePlatform.cs
+++ b/src/Avalonia.Native/AvaloniaNativePlatform.cs
@@ -111,7 +111,8 @@ namespace Avalonia.Native
                 .Bind<ISystemDialogImpl>().ToConstant(new SystemDialogs(_factory.CreateSystemDialogs()))
                 .Bind<PlatformHotkeyConfiguration>().ToConstant(new PlatformHotkeyConfiguration(KeyModifiers.Meta))
                 .Bind<IMountedVolumeInfoProvider>().ToConstant(new MacOSMountedVolumeInfoProvider())
-                .Bind<IPlatformDragSource>().ToConstant(new AvaloniaNativeDragSource(_factory));
+                .Bind<IPlatformDragSource>().ToConstant(new AvaloniaNativeDragSource(_factory))
+                .Bind<IPlatformLifetimeEventsImpl>().ToConstant(applicationPlatform);
 
             if (_options.UseGpu)
             {
diff --git a/src/Avalonia.Native/WindowImpl.cs b/src/Avalonia.Native/WindowImpl.cs
index f3b60f07be..f740be44a2 100644
--- a/src/Avalonia.Native/WindowImpl.cs
+++ b/src/Avalonia.Native/WindowImpl.cs
@@ -114,7 +114,7 @@ namespace Avalonia.Native
                 {
                     var visual = (_inputRoot as Window).Renderer.HitTestFirst(e.Position, _inputRoot as Window, x =>
                             {
-                                if (x is IInputElement ie && !ie.IsHitTestVisible)
+                                if (x is IInputElement ie && (!ie.IsHitTestVisible || !ie.IsVisible))
                                 {
                                     return false;
                                 }
diff --git a/src/Avalonia.Native/avn.idl b/src/Avalonia.Native/avn.idl
index 89e20463d8..d75d914044 100644
--- a/src/Avalonia.Native/avn.idl
+++ b/src/Avalonia.Native/avn.idl
@@ -733,4 +733,5 @@ interface IAvnNativeControlHostTopLevelAttachment : IUnknown
 interface IAvnApplicationEvents : IUnknown
 {
      void FilesOpened (IAvnStringArray* urls);
+     bool TryShutdown();
 }
diff --git a/src/Avalonia.Themes.Default/TextBox.xaml b/src/Avalonia.Themes.Default/TextBox.xaml
index c68355a57d..12df4b6213 100644
--- a/src/Avalonia.Themes.Default/TextBox.xaml
+++ b/src/Avalonia.Themes.Default/TextBox.xaml
@@ -4,7 +4,7 @@
     <StreamGeometry x:Key="PasswordBoxRevealButtonData">m10.051 7.0032c2.215 0 4.0105 1.7901 4.0105 3.9984s-1.7956 3.9984-4.0105 3.9984c-2.215 0-4.0105-1.7901-4.0105-3.9984s1.7956-3.9984 4.0105-3.9984zm0 1.4994c-1.3844 0-2.5066 1.1188-2.5066 2.499s1.1222 2.499 2.5066 2.499 2.5066-1.1188 2.5066-2.499-1.1222-2.499-2.5066-2.499zm0-5.0026c4.6257 0 8.6188 3.1487 9.7267 7.5613 0.10085 0.40165-0.14399 0.80877-0.54686 0.90931-0.40288 0.10054-0.81122-0.14355-0.91208-0.54521-0.94136-3.7492-4.3361-6.4261-8.2678-6.4261-3.9334 0-7.3292 2.6792-8.2689 6.4306-0.10063 0.40171-0.50884 0.64603-0.91177 0.54571s-0.648-0.5073-0.54737-0.90901c1.106-4.4152 5.1003-7.5667 9.728-7.5667z</StreamGeometry>
     <StreamGeometry x:Key="PasswordBoxHideButtonData">m0.21967 0.21965c-0.26627 0.26627-0.29047 0.68293-0.07262 0.97654l0.07262 0.08412 4.0346 4.0346c-1.922 1.3495-3.3585 3.365-3.9554 5.7495-0.10058 0.4018 0.14362 0.8091 0.54543 0.9097 0.40182 0.1005 0.80909-0.1436 0.90968-0.5455 0.52947-2.1151 1.8371-3.8891 3.5802-5.0341l1.8096 1.8098c-0.70751 0.7215-1.1438 1.71-1.1438 2.8003 0 2.2092 1.7909 4 4 4 1.0904 0 2.0788-0.4363 2.8004-1.1438l5.9193 5.9195c0.2929 0.2929 0.7677 0.2929 1.0606 0 0.2663-0.2662 0.2905-0.6829 0.0726-0.9765l-0.0726-0.0841-6.1135-6.1142 0.0012-0.0015-1.2001-1.1979-2.8699-2.8693 2e-3 -8e-4 -2.8812-2.8782 0.0012-0.0018-1.1333-1.1305-4.3064-4.3058c-0.29289-0.29289-0.76777-0.29289-1.0607 0zm7.9844 9.0458 3.5351 3.5351c-0.45 0.4358-1.0633 0.704-1.7392 0.704-1.3807 0-2.5-1.1193-2.5-2.5 0-0.6759 0.26824-1.2892 0.7041-1.7391zm1.7959-5.7655c-1.0003 0-1.9709 0.14807-2.8889 0.425l1.237 1.2362c0.5358-0.10587 1.0883-0.16119 1.6519-0.16119 3.9231 0 7.3099 2.6803 8.2471 6.4332 0.1004 0.4018 0.5075 0.6462 0.9094 0.5459 0.4019-0.1004 0.6463-0.5075 0.5459-0.9094-1.103-4.417-5.0869-7.5697-9.7024-7.5697zm0.1947 3.5093 3.8013 3.8007c-0.1018-2.0569-1.7488-3.7024-3.8013-3.8007z</StreamGeometry>
 
-    <MenuFlyout x:Key="DefaultTextBoxContextFlyout">
+    <MenuFlyout x:Key="DefaultTextBoxContextFlyout" Placement="Bottom">
       <MenuItem x:Name="TextBoxContextFlyoutCutItem" Header="Cut" Command="{Binding $parent[TextBox].Cut}" IsEnabled="{Binding $parent[TextBox].CanCut}" InputGesture="{x:Static TextBox.CutGesture}" />
       <MenuItem x:Name="TextBoxContextFlyoutCopyItem" Header="Copy" Command="{Binding $parent[TextBox].Copy}" IsEnabled="{Binding $parent[TextBox].CanCopy}" InputGesture="{x:Static TextBox.CopyGesture}"/>
       <MenuItem x:Name="TextBoxContextFlyoutPasteItem" Header="Paste" Command="{Binding $parent[TextBox].Paste}" IsEnabled="{Binding $parent[TextBox].CanPaste}" InputGesture="{x:Static TextBox.PasteGesture}"/>
diff --git a/src/Avalonia.Themes.Fluent/Controls/TextBox.xaml b/src/Avalonia.Themes.Fluent/Controls/TextBox.xaml
index 855143f592..fca4a3bd45 100644
--- a/src/Avalonia.Themes.Fluent/Controls/TextBox.xaml
+++ b/src/Avalonia.Themes.Fluent/Controls/TextBox.xaml
@@ -15,7 +15,7 @@
     <StreamGeometry x:Key="PasswordBoxRevealButtonData">m10.051 7.0032c2.215 0 4.0105 1.7901 4.0105 3.9984s-1.7956 3.9984-4.0105 3.9984c-2.215 0-4.0105-1.7901-4.0105-3.9984s1.7956-3.9984 4.0105-3.9984zm0 1.4994c-1.3844 0-2.5066 1.1188-2.5066 2.499s1.1222 2.499 2.5066 2.499 2.5066-1.1188 2.5066-2.499-1.1222-2.499-2.5066-2.499zm0-5.0026c4.6257 0 8.6188 3.1487 9.7267 7.5613 0.10085 0.40165-0.14399 0.80877-0.54686 0.90931-0.40288 0.10054-0.81122-0.14355-0.91208-0.54521-0.94136-3.7492-4.3361-6.4261-8.2678-6.4261-3.9334 0-7.3292 2.6792-8.2689 6.4306-0.10063 0.40171-0.50884 0.64603-0.91177 0.54571s-0.648-0.5073-0.54737-0.90901c1.106-4.4152 5.1003-7.5667 9.728-7.5667z</StreamGeometry>
     <StreamGeometry x:Key="PasswordBoxHideButtonData">m0.21967 0.21965c-0.26627 0.26627-0.29047 0.68293-0.07262 0.97654l0.07262 0.08412 4.0346 4.0346c-1.922 1.3495-3.3585 3.365-3.9554 5.7495-0.10058 0.4018 0.14362 0.8091 0.54543 0.9097 0.40182 0.1005 0.80909-0.1436 0.90968-0.5455 0.52947-2.1151 1.8371-3.8891 3.5802-5.0341l1.8096 1.8098c-0.70751 0.7215-1.1438 1.71-1.1438 2.8003 0 2.2092 1.7909 4 4 4 1.0904 0 2.0788-0.4363 2.8004-1.1438l5.9193 5.9195c0.2929 0.2929 0.7677 0.2929 1.0606 0 0.2663-0.2662 0.2905-0.6829 0.0726-0.9765l-0.0726-0.0841-6.1135-6.1142 0.0012-0.0015-1.2001-1.1979-2.8699-2.8693 2e-3 -8e-4 -2.8812-2.8782 0.0012-0.0018-1.1333-1.1305-4.3064-4.3058c-0.29289-0.29289-0.76777-0.29289-1.0607 0zm7.9844 9.0458 3.5351 3.5351c-0.45 0.4358-1.0633 0.704-1.7392 0.704-1.3807 0-2.5-1.1193-2.5-2.5 0-0.6759 0.26824-1.2892 0.7041-1.7391zm1.7959-5.7655c-1.0003 0-1.9709 0.14807-2.8889 0.425l1.237 1.2362c0.5358-0.10587 1.0883-0.16119 1.6519-0.16119 3.9231 0 7.3099 2.6803 8.2471 6.4332 0.1004 0.4018 0.5075 0.6462 0.9094 0.5459 0.4019-0.1004 0.6463-0.5075 0.5459-0.9094-1.103-4.417-5.0869-7.5697-9.7024-7.5697zm0.1947 3.5093 3.8013 3.8007c-0.1018-2.0569-1.7488-3.7024-3.8013-3.8007z</StreamGeometry>
 
-    <MenuFlyout x:Key="DefaultTextBoxContextFlyout">
+    <MenuFlyout x:Key="DefaultTextBoxContextFlyout" Placement="Bottom">
       <MenuItem x:Name="TextBoxContextFlyoutCutItem" Header="Cut" Command="{Binding $parent[TextBox].Cut}" IsEnabled="{Binding $parent[TextBox].CanCut}" InputGesture="{x:Static TextBox.CutGesture}" />
       <MenuItem x:Name="TextBoxContextFlyoutCopyItem" Header="Copy" Command="{Binding $parent[TextBox].Copy}" IsEnabled="{Binding $parent[TextBox].CanCopy}" InputGesture="{x:Static TextBox.CopyGesture}"/>
       <MenuItem x:Name="TextBoxContextFlyoutPasteItem" Header="Paste" Command="{Binding $parent[TextBox].Paste}" IsEnabled="{Binding $parent[TextBox].CanPaste}" InputGesture="{x:Static TextBox.PasteGesture}"/>
@@ -76,9 +76,7 @@
                                 IsVisible="{TemplateBinding Text, Converter={x:Static StringConverters.IsNullOrEmpty}}"
                                 HorizontalAlignment="{TemplateBinding HorizontalContentAlignment}" 
                                 VerticalAlignment="{TemplateBinding VerticalContentAlignment}"/>
-                        <!-- TODO eliminate this margin... text layout issue? -->
                         <TextPresenter Name="PART_TextPresenter"
-                                      Margin="0 1 0 0"
                                       Text="{TemplateBinding Text, Mode=TwoWay}"
                                       CaretIndex="{TemplateBinding CaretIndex}"
                                       SelectionStart="{TemplateBinding SelectionStart}"
diff --git a/src/Avalonia.Visuals/Media/GlyphRun.cs b/src/Avalonia.Visuals/Media/GlyphRun.cs
index 2b787462e4..234122f6f5 100644
--- a/src/Avalonia.Visuals/Media/GlyphRun.cs
+++ b/src/Avalonia.Visuals/Media/GlyphRun.cs
@@ -582,7 +582,7 @@ namespace Avalonia.Media
                 {
                     var cluster = _glyphClusters[i];
 
-                    var codepointIndex = cluster - _characters.Start;
+                    var codepointIndex = IsLeftToRight ? cluster - _characters.Start : _characters.End - cluster;
 
                     var codepoint = Codepoint.ReadAt(_characters, codepointIndex, out _);
 
diff --git a/src/Avalonia.Visuals/Media/TextFormatting/ShapedTextCharacters.cs b/src/Avalonia.Visuals/Media/TextFormatting/ShapedTextCharacters.cs
index 3c17dabbb0..33d1b30e3c 100644
--- a/src/Avalonia.Visuals/Media/TextFormatting/ShapedTextCharacters.cs
+++ b/src/Avalonia.Visuals/Media/TextFormatting/ShapedTextCharacters.cs
@@ -90,7 +90,9 @@ namespace Avalonia.Media.TextFormatting
         /// <returns>The split result.</returns>
         public SplitTextCharactersResult Split(int length)
         {
-            var glyphCount = GlyphRun.FindGlyphIndex(GlyphRun.Characters.Start + length);
+            var glyphCount = GlyphRun.IsLeftToRight ?
+                GlyphRun.FindGlyphIndex(GlyphRun.Characters.Start + length) :
+                GlyphRun.FindGlyphIndex(GlyphRun.Characters.End - length);
 
             if (GlyphRun.Characters.Length == length)
             {
@@ -102,31 +104,64 @@ namespace Avalonia.Media.TextFormatting
                 return new SplitTextCharactersResult(this, null);
             }
 
-            var firstGlyphRun = new GlyphRun(
-                Properties.Typeface.GlyphTypeface,
-                Properties.FontRenderingEmSize,
-                GlyphRun.GlyphIndices.Take(glyphCount),
-                GlyphRun.GlyphAdvances.Take(glyphCount),
-                GlyphRun.GlyphOffsets.Take(glyphCount),
-                GlyphRun.Characters.Take(length),
-                GlyphRun.GlyphClusters.Take(glyphCount),
-                GlyphRun.BiDiLevel);
-
-            var firstTextRun = new ShapedTextCharacters(firstGlyphRun, Properties);
-
-            var secondGlyphRun = new GlyphRun(
-                Properties.Typeface.GlyphTypeface,
-                Properties.FontRenderingEmSize,
-                GlyphRun.GlyphIndices.Skip(glyphCount),
-                GlyphRun.GlyphAdvances.Skip(glyphCount),
-                GlyphRun.GlyphOffsets.Skip(glyphCount),
-                GlyphRun.Characters.Skip(length),
-                GlyphRun.GlyphClusters.Skip(glyphCount),
-                GlyphRun.BiDiLevel);
-
-            var secondTextRun = new ShapedTextCharacters(secondGlyphRun, Properties);
-
-            return new SplitTextCharactersResult(firstTextRun, secondTextRun);
+            if (GlyphRun.IsLeftToRight)
+            {
+                var firstGlyphRun = new GlyphRun(
+                    Properties.Typeface.GlyphTypeface,
+                    Properties.FontRenderingEmSize,
+                    GlyphRun.GlyphIndices.Take(glyphCount),
+                    GlyphRun.GlyphAdvances.Take(glyphCount),
+                    GlyphRun.GlyphOffsets.Take(glyphCount),
+                    GlyphRun.Characters.Take(length),
+                    GlyphRun.GlyphClusters.Take(glyphCount),
+                    GlyphRun.BiDiLevel);
+
+                var firstTextRun = new ShapedTextCharacters(firstGlyphRun, Properties);
+
+                var secondGlyphRun = new GlyphRun(
+                    Properties.Typeface.GlyphTypeface,
+                    Properties.FontRenderingEmSize,
+                    GlyphRun.GlyphIndices.Skip(glyphCount),
+                    GlyphRun.GlyphAdvances.Skip(glyphCount),
+                    GlyphRun.GlyphOffsets.Skip(glyphCount),
+                    GlyphRun.Characters.Skip(length),
+                    GlyphRun.GlyphClusters.Skip(glyphCount),
+                    GlyphRun.BiDiLevel);
+
+                var secondTextRun = new ShapedTextCharacters(secondGlyphRun, Properties);
+
+                return new SplitTextCharactersResult(firstTextRun, secondTextRun);
+            }
+            else
+            {
+                var take = GlyphRun.GlyphIndices.Length - glyphCount;
+                
+                var firstGlyphRun = new GlyphRun(
+                    Properties.Typeface.GlyphTypeface,
+                    Properties.FontRenderingEmSize,
+                    GlyphRun.GlyphIndices.Take(take),
+                    GlyphRun.GlyphAdvances.Take(take),
+                    GlyphRun.GlyphOffsets.Take(take),
+                    GlyphRun.Characters.Skip(length),
+                    GlyphRun.GlyphClusters.Take(take),
+                    GlyphRun.BiDiLevel);
+
+                var firstTextRun = new ShapedTextCharacters(firstGlyphRun, Properties);
+
+                var secondGlyphRun = new GlyphRun(
+                    Properties.Typeface.GlyphTypeface,
+                    Properties.FontRenderingEmSize,
+                    GlyphRun.GlyphIndices.Skip(take),
+                    GlyphRun.GlyphAdvances.Skip(take),
+                    GlyphRun.GlyphOffsets.Skip(take),
+                    GlyphRun.Characters.Take(length),
+                    GlyphRun.GlyphClusters.Skip(take),
+                    GlyphRun.BiDiLevel);
+
+                var secondTextRun = new ShapedTextCharacters(secondGlyphRun, Properties);
+
+                return new SplitTextCharactersResult(secondTextRun,firstTextRun);
+            }
         }
 
         public readonly struct SplitTextCharactersResult
diff --git a/src/Avalonia.Visuals/Media/TextFormatting/TextCharacters.cs b/src/Avalonia.Visuals/Media/TextFormatting/TextCharacters.cs
index 0779716ec8..cfca8f9ab2 100644
--- a/src/Avalonia.Visuals/Media/TextFormatting/TextCharacters.cs
+++ b/src/Avalonia.Visuals/Media/TextFormatting/TextCharacters.cs
@@ -134,7 +134,7 @@ namespace Avalonia.Media.TextFormatting
             var isFallback = typeface != defaultTypeface;
 
             count = 0;
-            var script = Script.Common;
+            var script = Script.Unknown;
             var direction = BiDiClass.LeftToRight;
 
             var font = typeface.GlyphTypeface;
@@ -161,7 +161,7 @@ namespace Avalonia.Media.TextFormatting
 
                 if (currentScript != script)
                 {
-                    if (script == Script.Inherited || script == Script.Common)
+                    if (script is Script.Unknown)
                     {
                         script = currentScript;
                     }
@@ -174,13 +174,16 @@ namespace Avalonia.Media.TextFormatting
                     }
                 }
 
-                if (currentScript != Script.Common && currentScript != Script.Inherited)
+                //Only handle non whitespace here
+                if (!currentGrapheme.FirstCodepoint.IsWhiteSpace)
                 {
+                    //Stop at the first glyph that is present in the default typeface.
                     if (isFallback && defaultFont.TryGetGlyph(currentGrapheme.FirstCodepoint, out _))
                     {
                         break;
                     }
 
+                    //Stop at the first missing glyph
                     if (!font.TryGetGlyph(currentGrapheme.FirstCodepoint, out _))
                     {
                         break;
diff --git a/src/Avalonia.Visuals/Media/TextFormatting/TextFormatterImpl.cs b/src/Avalonia.Visuals/Media/TextFormatting/TextFormatterImpl.cs
index 6533c34ba0..df63b00c25 100644
--- a/src/Avalonia.Visuals/Media/TextFormatting/TextFormatterImpl.cs
+++ b/src/Avalonia.Visuals/Media/TextFormatting/TextFormatterImpl.cs
@@ -70,34 +70,74 @@ namespace Avalonia.Media.TextFormatting
             {
                 var glyphTypeface = glyphRun.GlyphTypeface;
 
-                for (var i = 0; i < glyphRun.GlyphClusters.Length; i++)
+                if (glyphRun.IsLeftToRight)
                 {
-                    var glyph = glyphRun.GlyphIndices[i];
+                    foreach (var glyph in glyphRun.GlyphIndices)
+                    {
+                        var advance = glyphTypeface.GetGlyphAdvance(glyph) * glyphRun.Scale;
 
-                    var advance = glyphTypeface.GetGlyphAdvance(glyph) * glyphRun.Scale;
+                        if (currentWidth + advance > availableWidth)
+                        {
+                            break;
+                        }
 
-                    if (currentWidth + advance > availableWidth)
-                    {
-                        break;
+                        currentWidth += advance;
+
+                        glyphCount++;
                     }
+                }
+                else
+                {
+                    for (var index = glyphRun.GlyphClusters.Length - 1; index > 0; index--)
+                    {
+                        var glyph = glyphRun.GlyphIndices[index];
+
+                        var advance = glyphTypeface.GetGlyphAdvance(glyph) * glyphRun.Scale;
 
-                    currentWidth += advance;
+                        if (currentWidth + advance > availableWidth)
+                        {
+                            break;
+                        }
 
-                    glyphCount++;
+                        currentWidth += advance;
+
+                        glyphCount++;
+                    }
                 }
             }
             else
             {
-                foreach (var advance in glyphRun.GlyphAdvances)
+                if (glyphRun.IsLeftToRight)
                 {
-                    if (currentWidth + advance > availableWidth)
+                    for (var index = 0; index < glyphRun.GlyphAdvances.Length; index++)
                     {
-                        break;
+                        var advance = glyphRun.GlyphAdvances[index];
+                    
+                        if (currentWidth + advance > availableWidth)
+                        {
+                            break;
+                        }
+
+                        currentWidth += advance;
+
+                        glyphCount++;
                     }
+                }
+                else
+                {
+                    for (var index = glyphRun.GlyphAdvances.Length - 1; index > 0; index--)
+                    {
+                        var advance = glyphRun.GlyphAdvances[index];
+                    
+                        if (currentWidth + advance > availableWidth)
+                        {
+                            break;
+                        }
 
-                    currentWidth += advance;
+                        currentWidth += advance;
 
-                    glyphCount++;
+                        glyphCount++;
+                    }
                 }
             }
 
@@ -475,24 +515,14 @@ namespace Avalonia.Media.TextFormatting
 
             var remainingCharacters = splitResult.Second;
 
-            if (currentLineBreak?.RemainingCharacters != null)
+            var lineBreak = remainingCharacters?.Count > 0 ? new TextLineBreak(remainingCharacters) : null;
+
+            if (lineBreak is null && currentLineBreak.TextEndOfLine != null)
             {
-                if (remainingCharacters != null)
-                {
-                    remainingCharacters.AddRange(currentLineBreak.RemainingCharacters);
-                }
-                else
-                {
-                    remainingCharacters = new List<ShapedTextCharacters>(currentLineBreak.RemainingCharacters);
-                }
+                lineBreak = new TextLineBreak(currentLineBreak.TextEndOfLine);
             }
 
-            var lineBreak = remainingCharacters != null && remainingCharacters.Count > 0 ?
-                new TextLineBreak(remainingCharacters) :
-                null;
-
-            return new TextLineImpl(splitResult.First, textRange, paragraphWidth, paragraphProperties,
-                lineBreak);
+            return new TextLineImpl(splitResult.First, textRange, paragraphWidth, paragraphProperties, lineBreak);
         }
 
         /// <summary>
diff --git a/src/Avalonia.Visuals/Rendering/SceneGraph/SceneBuilder.cs b/src/Avalonia.Visuals/Rendering/SceneGraph/SceneBuilder.cs
index f2a09b815e..c6cdf474bb 100644
--- a/src/Avalonia.Visuals/Rendering/SceneGraph/SceneBuilder.cs
+++ b/src/Avalonia.Visuals/Rendering/SceneGraph/SceneBuilder.cs
@@ -258,14 +258,25 @@ namespace Avalonia.Rendering.SceneGraph
                         }
                         else if (visualChildren.Count > 1)
                         {
-                            var sortedChildren = new IVisual[visualChildren.Count];
-                            visualChildren.CopyTo(sortedChildren, 0);
+                            var count = visualChildren.Count;
+                            var sortedChildren = new (IVisual visual, int index)[count];
 
-                            Array.Sort(sortedChildren, ZIndexComparer.ComparisonInstance);
+                            for (var i = 0; i < count; i++)
+                            {
+                                sortedChildren[i] = (visualChildren[i], i);
+                            }
+
+                            // Regular Array.Sort is unstable, we need to provide indices as well to avoid reshuffling elements.
+                            Array.Sort(sortedChildren, (lhs, rhs) =>
+                            {
+                                var result = ZIndexComparer.Instance.Compare(lhs.visual, rhs.visual);
+
+                                return result == 0 ? lhs.index.CompareTo(rhs.index) : result;
+                            });
 
                             foreach (var child in sortedChildren)
                             {
-                                var childNode = GetOrCreateChildNode(scene, child, node);
+                                var childNode = GetOrCreateChildNode(scene, child.Item1, node);
                                 Update(context, scene, (VisualNode)childNode, clip, forceRecurse);
                             }
                         }
diff --git a/src/Windows/Avalonia.Win32/Win32Platform.cs b/src/Windows/Avalonia.Win32/Win32Platform.cs
index d92bd08d01..84e61ca007 100644
--- a/src/Windows/Avalonia.Win32/Win32Platform.cs
+++ b/src/Windows/Avalonia.Win32/Win32Platform.cs
@@ -112,7 +112,14 @@ namespace Avalonia.Win32
                 .Bind<IRenderTimer>().ToConstant(new DefaultRenderTimer(60))
                 .Bind<ISystemDialogImpl>().ToSingleton<SystemDialogImpl>()
                 .Bind<IWindowingPlatform>().ToConstant(s_instance)
-                .Bind<PlatformHotkeyConfiguration>().ToSingleton<PlatformHotkeyConfiguration>()
+                .Bind<PlatformHotkeyConfiguration>().ToConstant(new PlatformHotkeyConfiguration(KeyModifiers.Control)
+                {
+                    OpenContextMenu =
+                    {
+                        // Add Shift+F10
+                        new KeyGesture(Key.F10, KeyModifiers.Shift)
+                    }
+                })
                 .Bind<IPlatformIconLoader>().ToConstant(s_instance)
                 .Bind<NonPumpingLockHelper.IHelperImpl>().ToConstant(new NonPumpingSyncContext.HelperImpl())
                 .Bind<IMountedVolumeInfoProvider>().ToConstant(new WindowsMountedVolumeInfoProvider());
diff --git a/tests/Avalonia.Controls.UnitTests/ContextMenuTests.cs b/tests/Avalonia.Controls.UnitTests/ContextMenuTests.cs
index f3a1316c7d..3ed0af39a2 100644
--- a/tests/Avalonia.Controls.UnitTests/ContextMenuTests.cs
+++ b/tests/Avalonia.Controls.UnitTests/ContextMenuTests.cs
@@ -1,11 +1,12 @@
 using System;
+
+using Avalonia.Controls.Primitives;
 using Avalonia.Input;
-using Avalonia.LogicalTree;
 using Avalonia.Markup.Xaml;
-using Avalonia.Markup.Xaml.MarkupExtensions;
 using Avalonia.Platform;
+using Avalonia.Rendering;
 using Avalonia.UnitTests;
-using Castle.DynamicProxy.Generators;
+
 using Moq;
 using Xunit;
 
@@ -16,6 +17,107 @@ namespace Avalonia.Controls.UnitTests
         private Mock<IPopupImpl> popupImpl;
         private MouseTestHelper _mouse = new MouseTestHelper();
 
+        [Fact]
+        public void ContextRequested_Opens_ContextMenu()
+        {
+            using (Application())
+            {
+                var sut = new ContextMenu();
+                var target = new Panel
+                {
+                    ContextMenu = sut
+                };
+
+                var window = new Window { Content = target };
+                window.ApplyTemplate();
+                window.Presenter.ApplyTemplate();
+
+                int openedCount = 0;
+
+                sut.MenuOpened += (sender, args) =>
+                {
+                    openedCount++;
+                };
+
+                target.RaiseEvent(new ContextRequestedEventArgs());
+
+                Assert.True(sut.IsOpen);
+                Assert.Equal(1, openedCount);
+            }
+        }
+
+        [Fact]
+        public void ContextMenu_Is_Opened_When_ContextFlyout_Is_Also_Set()
+        {
+            // We have this test for backwards compatability with the code that already sets custom ContextMenu.
+            using (Application())
+            {
+                var sut = new ContextMenu();
+                var flyout = new Flyout();
+                var target = new Panel
+                {
+                    ContextMenu = sut,
+                    ContextFlyout = flyout
+                };
+
+                var window = new Window { Content = target };
+                window.ApplyTemplate();
+                window.Presenter.ApplyTemplate();
+
+                target.RaiseEvent(new ContextRequestedEventArgs());
+
+                Assert.True(sut.IsOpen);
+                Assert.False(flyout.IsOpen);
+            }
+        }
+
+        [Fact]
+        public void KeyUp_Raised_On_Target_Opens_ContextFlyout()
+        {
+            using (Application())
+            {
+                var sut = new ContextMenu();
+                var target = new Panel
+                {
+                    ContextMenu = sut
+                };
+                var contextRequestedCount = 0;
+                target.AddHandler(Control.ContextRequestedEvent, (s, a) => contextRequestedCount++, Interactivity.RoutingStrategies.Tunnel);
+
+                var window = PreparedWindow(target);
+                window.Show();
+
+                target.RaiseEvent(new KeyEventArgs { RoutedEvent = InputElement.KeyUpEvent, Key = Key.Apps, Source = window });
+
+                Assert.True(sut.IsOpen);
+                Assert.Equal(1, contextRequestedCount);
+            }
+        }
+
+        [Fact]
+        public void KeyUp_Raised_On_Flyout_Closes_Opened_ContextMenu()
+        {
+            using (Application())
+            {
+                var sut = new ContextMenu();
+                var target = new Panel
+                {
+                    ContextMenu = sut
+                };
+
+                var window = PreparedWindow(target);
+                window.Show();
+
+                target.RaiseEvent(new ContextRequestedEventArgs());
+
+                Assert.True(sut.IsOpen);
+
+                sut.RaiseEvent(new KeyEventArgs { RoutedEvent = InputElement.KeyUpEvent, Key = Key.Apps, Source = window });
+
+                Assert.False(sut.IsOpen);
+            }
+        }
+
         [Fact]
         public void Opening_Raises_Single_Opened_Event()
         {
@@ -123,6 +225,91 @@ namespace Avalonia.Controls.UnitTests
             }
         }
 
+        [Fact]
+        public void Cancel_Light_Dismiss_Closing_Keeps_Flyout_Open()
+        {
+            using (Application())
+            {
+                popupImpl.Setup(x => x.Show(true)).Verifiable();
+                popupImpl.Setup(x => x.Hide()).Verifiable();
+
+                var window = PreparedWindow();
+                window.Width = 100;
+                window.Height = 100;
+
+                var button = new Button
+                {
+                    Height = 10,
+                    Width = 10,
+                    HorizontalAlignment = Layout.HorizontalAlignment.Left,
+                    VerticalAlignment = Layout.VerticalAlignment.Top
+                };
+                window.Content = button;
+
+                window.ApplyTemplate();
+                window.Show();
+
+                var tracker = 0;
+
+                var c = new ContextMenu();
+                c.ContextMenuClosing += (s, e) =>
+                {
+                    tracker++;
+                    e.Cancel = true;
+                };
+                button.ContextMenu = c;
+                c.Open(button);
+
+                var overlay = LightDismissOverlayLayer.GetLightDismissOverlayLayer(window);
+                _mouse.Down(overlay, MouseButton.Left, new Point(90, 90));
+                _mouse.Up(button, MouseButton.Left, new Point(90, 90));
+
+                Assert.Equal(1, tracker);
+                Assert.True(c.IsOpen);
+
+                popupImpl.Verify(x => x.Hide(), Times.Never);
+                popupImpl.Verify(x => x.Show(true), Times.Exactly(1));
+            }
+        }
+
+        [Fact]
+        public void Light_Dismiss_Closes_Flyout()
+        {
+            using (Application())
+            {
+                popupImpl.Setup(x => x.Show(true)).Verifiable();
+                popupImpl.Setup(x => x.Hide()).Verifiable();
+
+                var window = PreparedWindow();
+                window.Width = 100;
+                window.Height = 100;
+
+                var button = new Button
+                {
+                    Height = 10,
+                    Width = 10,
+                    HorizontalAlignment = Layout.HorizontalAlignment.Left,
+                    VerticalAlignment = Layout.VerticalAlignment.Top
+                };
+                window.Content = button;
+
+                window.ApplyTemplate();
+                window.Show();
+
+                var c = new ContextMenu();
+                c.PlacementMode = PlacementMode.Bottom;
+                c.Open(button);
+
+                var overlay = LightDismissOverlayLayer.GetLightDismissOverlayLayer(window);
+                _mouse.Down(overlay, MouseButton.Left, new Point(90, 90));
+                _mouse.Up(button, MouseButton.Left, new Point(90, 90));
+
+                Assert.False(c.IsOpen);
+                popupImpl.Verify(x => x.Hide(), Times.Exactly(1));
+                popupImpl.Verify(x => x.Show(true), Times.Exactly(1));
+            }
+        }
+
         [Fact]
         public void Clicking_On_Control_Toggles_ContextMenu()
         {
@@ -137,15 +324,16 @@ namespace Avalonia.Controls.UnitTests
                     ContextMenu = sut
                 };
 
-                var window = new Window {Content = target};
-                window.ApplyTemplate();
-                window.Presenter.ApplyTemplate();
+                var window = PreparedWindow(target);
+                window.Show();
+                var overlay = LightDismissOverlayLayer.GetLightDismissOverlayLayer(window);
 
                 _mouse.Click(target, MouseButton.Right);
 
                 Assert.True(sut.IsOpen);
 
-                _mouse.Click(target);
+                _mouse.Down(overlay);
+                _mouse.Up(target);
 
                 Assert.False(sut.IsOpen);
                 popupImpl.Verify(x => x.Show(true), Times.Once);
@@ -167,15 +355,16 @@ namespace Avalonia.Controls.UnitTests
                     ContextMenu = sut
                 };
 
-                var window = new Window {Content = target};
-                window.ApplyTemplate();
-                window.Presenter.ApplyTemplate();
+                var window = PreparedWindow(target);
+                window.Show();
 
-                _mouse.Click(target, MouseButton.Right);
+                var overlay = LightDismissOverlayLayer.GetLightDismissOverlayLayer(window);
 
+                _mouse.Click(target, MouseButton.Right);
                 Assert.True(sut.IsOpen);
 
-                _mouse.Click(target, MouseButton.Right);
+                _mouse.Down(overlay, MouseButton.Right);
+                _mouse.Up(target, MouseButton.Right);
 
                 Assert.True(sut.IsOpen);
                 popupImpl.Verify(x => x.Hide(), Times.Once);
@@ -209,12 +398,10 @@ namespace Avalonia.Controls.UnitTests
 
                 Assert.True(sut.IsOpen);
 
-                _mouse.Click(target2, MouseButton.Left);
-                
-                Assert.False(sut.IsOpen);
-                
                 sp.Children.Remove(target1);
-                
+
+                Assert.False(sut.IsOpen);
+
                 _mouse.Click(target2, MouseButton.Right);
                 
                 Assert.True(sut.IsOpen);
@@ -341,7 +528,7 @@ namespace Avalonia.Controls.UnitTests
             }
         }
 
-        [Fact(Skip = "The only reason this test was 'passing' before was that the author forgot to call Window.ApplyTemplate()")]
+        [Fact]
         public void Cancelling_Closing_Leaves_ContextMenuOpen()
         {
             using (Application())
@@ -355,17 +542,20 @@ namespace Avalonia.Controls.UnitTests
                 {
                     ContextMenu = sut
                 };
-                
-                var window = new Window {Content = target};
-                window.ApplyTemplate();
+
+                var window = PreparedWindow(target);
+                var overlay = LightDismissOverlayLayer.GetLightDismissOverlayLayer(window);
 
                 sut.ContextMenuClosing += (c, e) => { eventCalled = true; e.Cancel = true; };
 
+                window.Show();
+
                 _mouse.Click(target, MouseButton.Right);
 
                 Assert.True(sut.IsOpen);
 
-                _mouse.Click(target, MouseButton.Right);
+                _mouse.Down(overlay, MouseButton.Right);
+                _mouse.Up(target, MouseButton.Right);
 
                 Assert.True(eventCalled);
                 Assert.True(sut.IsOpen);
@@ -375,6 +565,19 @@ namespace Avalonia.Controls.UnitTests
             }
         }
 
+        private Window PreparedWindow(object content = null)
+        {
+            var renderer = new Mock<IRenderer>();
+            var platform = AvaloniaLocator.Current.GetService<IWindowingPlatform>();
+            var windowImpl = Mock.Get(platform.CreateWindow());
+            windowImpl.Setup(x => x.CreateRenderer(It.IsAny<IRenderRoot>())).Returns(renderer.Object);
+
+            var w = new Window(windowImpl.Object) { Content = content };
+            w.ApplyTemplate();
+            w.Presenter.ApplyTemplate();
+            return w;
+        }
+
         private IDisposable Application()
         {
             var screen = new PixelRect(new PixelPoint(), new PixelSize(100, 100));
diff --git a/tests/Avalonia.Controls.UnitTests/DesktopStyleApplicationLifetimeTests.cs b/tests/Avalonia.Controls.UnitTests/DesktopStyleApplicationLifetimeTests.cs
index 84f02aeda5..38713834c3 100644
--- a/tests/Avalonia.Controls.UnitTests/DesktopStyleApplicationLifetimeTests.cs
+++ b/tests/Avalonia.Controls.UnitTests/DesktopStyleApplicationLifetimeTests.cs
@@ -1,5 +1,6 @@
 using System;
 using System.Collections.Generic;
+using System.ComponentModel;
 using Avalonia.Controls.ApplicationLifetimes;
 using Avalonia.Platform;
 using Avalonia.Threading;
@@ -209,6 +210,33 @@ namespace Avalonia.Controls.UnitTests
                 Assert.Empty(lifetime.Windows);
             }
         }
+
+        [Fact]
+        public void Should_Allow_Canceling_Shutdown_Via_ShutdownRequested_Event()
+        {
+            using (UnitTestApplication.Start(TestServices.StyledWindow))
+            using (var lifetime = new ClassicDesktopStyleApplicationLifetime())
+            {
+                var lifetimeEvents = new Mock<IPlatformLifetimeEventsImpl>();
+                AvaloniaLocator.CurrentMutable.Bind<IPlatformLifetimeEventsImpl>().ToConstant(lifetimeEvents.Object);
+                lifetime.Start(Array.Empty<string>());
+
+                var window = new Window();
+                var raised = 0;
+
+                window.Show();
+
+                lifetime.ShutdownRequested += (s, e) =>
+                {
+                    e.Cancel = true;
+                    ++raised;
+                };
+
+                lifetimeEvents.Raise(x => x.ShutdownRequested += null, new CancelEventArgs());
+
+                Assert.Equal(1, raised);
+                Assert.Equal(new[] { window }, lifetime.Windows);
+            }
+        }
     }
-    
 }
diff --git a/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs b/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs
index 0dce73180e..c2dd8cf01a 100644
--- a/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs
+++ b/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs
@@ -1,10 +1,18 @@
 using System;
+using System.ComponentModel;
 using System.Linq;
+
+using Avalonia.Controls.Primitives;
 using Avalonia.Input;
 using Avalonia.Markup.Xaml;
 using Avalonia.Media;
+using Avalonia.Platform;
+using Avalonia.Rendering;
 using Avalonia.UnitTests;
 using Avalonia.VisualTree;
+
+using Moq;
+
 using Xunit;
 
 namespace Avalonia.Controls.UnitTests
@@ -28,6 +36,7 @@ namespace Avalonia.Controls.UnitTests
                 f.ShowAt(window);
 
                 Assert.Equal(1, tracker);
+                Assert.True(f.IsOpen);
             }
         }
 
@@ -51,6 +60,31 @@ namespace Avalonia.Controls.UnitTests
             }
         }
 
+        [Fact]
+        public void Opening_Is_Cancellable()
+        {
+            using (CreateServicesWithFocus())
+            {
+                var window = PreparedWindow();
+                window.Show();
+
+                int tracker = 0;
+                Flyout f = new Flyout();
+                f.Opening += (s, e) =>
+                {
+                    tracker++;
+                    if (e is CancelEventArgs cancelEventArgs)
+                    {
+                        cancelEventArgs.Cancel = true;
+                    }
+                };
+                f.ShowAt(window);
+
+                Assert.Equal(1, tracker);
+                Assert.False(f.IsOpen);
+            }
+        }
+
         [Fact]
         public void Closing_Raises_Single_Closing_Event()
         {
@@ -101,16 +135,89 @@ namespace Avalonia.Controls.UnitTests
                 var window = PreparedWindow();
                 window.Show();
 
-                int tracker = 0;
-                Flyout f = new Flyout();
+                var tracker = 0;
+                var f = new Flyout();
                 f.Closing += (s, e) =>
                 {
+                    tracker++;
                     e.Cancel = true;
                 };
                 f.ShowAt(window);
                 f.Hide();
 
                 Assert.True(f.IsOpen);
+                Assert.Equal(1, tracker);
+            }
+        }
+
+        [Fact]
+        public void Cancel_Light_Dismiss_Closing_Keeps_Flyout_Open()
+        {
+            using (CreateServicesWithFocus())
+            {
+                var window = PreparedWindow();
+                window.Width = 100;
+                window.Height = 100;
+
+                var button = new Button
+                {
+                    Height = 10,
+                    Width = 10,
+                    HorizontalAlignment = Layout.HorizontalAlignment.Left,
+                    VerticalAlignment = Layout.VerticalAlignment.Top
+                };
+                window.Content = button;
+
+                window.Show();
+
+                var tracker = 0;
+                var f = new Flyout();
+                f.Content = new Border { Width = 10, Height = 10 };
+                f.Closing += (s, e) =>
+                {
+                    tracker++;
+                    e.Cancel = true;
+                };
+                f.ShowAt(window);
+
+                var e = CreatePointerPressedEventArgs(window, new Point(90, 90));
+                var overlay = LightDismissOverlayLayer.GetLightDismissOverlayLayer(window);
+                overlay.RaiseEvent(e);
+
+                Assert.Equal(1, tracker);
+                Assert.True(f.IsOpen);
+            }
+        }
+
+        [Fact]
+        public void Light_Dismiss_Closes_Flyout()
+        {
+            using (CreateServicesWithFocus())
+            {
+                var window = PreparedWindow();
+                window.Width = 100;
+                window.Height = 100;
+
+                var button = new Button
+                {
+                    Height = 10,
+                    Width = 10,
+                    HorizontalAlignment = Layout.HorizontalAlignment.Left,
+                    VerticalAlignment = Layout.VerticalAlignment.Top
+                };
+                window.Content = button;
+
+                window.Show();
+
+                var f = new Flyout();
+                f.Content = new Border { Width = 10, Height = 10 };
+                f.ShowAt(window);
+
+                var e = CreatePointerPressedEventArgs(window, new Point(90, 90));
+                var overlay = LightDismissOverlayLayer.GetLightDismissOverlayLayer(window);
+                overlay.RaiseEvent(e);
+
+                Assert.False(f.IsOpen);
             }
         }
 
@@ -222,6 +329,109 @@ namespace Avalonia.Controls.UnitTests
             }
         }
 
+        [Fact]
+        public void ContextRequested_Opens_ContextFlyout()
+        {
+            using (CreateServicesWithFocus())
+            {
+                var flyout = new Flyout();
+                var target = new Panel
+                {
+                    ContextFlyout = flyout
+                };
+
+                var window = PreparedWindow(target);
+                window.Show();
+
+                int openedCount = 0;
+
+                flyout.Opened += (sender, args) =>
+                {
+                    openedCount++;
+                };
+
+                target.RaiseEvent(new ContextRequestedEventArgs());
+
+                Assert.True(flyout.IsOpen);
+                Assert.Equal(1, openedCount);
+            }
+        }
+
+        [Fact]
+        public void KeyUp_Raised_On_Target_Opens_ContextFlyout()
+        {
+            using (CreateServicesWithFocus())
+            {
+                var flyout = new Flyout();
+                var target = new Panel
+                {
+                    ContextFlyout = flyout
+                };
+                var contextRequestedCount = 0;
+                target.AddHandler(Control.ContextRequestedEvent, (s, a) => contextRequestedCount++, Interactivity.RoutingStrategies.Tunnel);
+
+                var window = PreparedWindow(target);
+                window.Show();
+
+                target.RaiseEvent(new KeyEventArgs { RoutedEvent = InputElement.KeyUpEvent, Key = Key.Apps, Source = window });
+
+                Assert.True(flyout.IsOpen);
+                Assert.Equal(1, contextRequestedCount);
+            }
+        }
+
+        [Fact]
+        public void KeyUp_Raised_On_Target_Closes_Opened_ContextFlyout()
+        {
+            using (CreateServicesWithFocus())
+            {
+                var flyout = new Flyout();
+                var target = new Panel
+                {
+                    ContextFlyout = flyout
+                };
+
+                var window = PreparedWindow(target);
+                window.Show();
+
+                target.RaiseEvent(new ContextRequestedEventArgs());
+
+                Assert.True(flyout.IsOpen);
+
+                target.RaiseEvent(new KeyEventArgs { RoutedEvent = InputElement.KeyUpEvent, Key = Key.Apps, Source = window });
+
+                Assert.False(flyout.IsOpen);
+            }
+        }
+
+        [Fact]
+        public void KeyUp_Raised_On_Flyout_Closes_Opened_ContextFlyout()
+        {
+            using (CreateServicesWithFocus())
+            {
+                var flyoutContent = new Button();
+                var flyout = new Flyout()
+                {
+                    Content = flyoutContent
+                };
+                var target = new Panel
+                {
+                    ContextFlyout = flyout
+                };
+
+                var window = PreparedWindow(target);
+                window.Show();
+
+                target.RaiseEvent(new ContextRequestedEventArgs());
+
+                Assert.True(flyout.IsOpen);
+
+                flyoutContent.RaiseEvent(new KeyEventArgs { RoutedEvent = InputElement.KeyUpEvent, Key = Key.Apps, Source = window });
+
+                Assert.False(flyout.IsOpen);
+            }
+        }
+
         [Fact]
         public void ContextFlyout_Can_Be_Set_In_Styles()
         {
@@ -317,9 +527,27 @@ namespace Avalonia.Controls.UnitTests
 
         private Window PreparedWindow(object content = null)
         {
-            var w = new Window { Content = content };
+            var renderer = new Mock<IRenderer>();
+            var platform = AvaloniaLocator.Current.GetService<IWindowingPlatform>();
+            var windowImpl = Mock.Get(platform.CreateWindow());
+            windowImpl.Setup(x => x.CreateRenderer(It.IsAny<IRenderRoot>())).Returns(renderer.Object);
+
+            var w = new Window(windowImpl.Object) { Content = content };
             w.ApplyTemplate();
             return w;
         }
+
+        private PointerPressedEventArgs CreatePointerPressedEventArgs(Window source, Point p)
+        {
+            var pointer = new Pointer(Pointer.GetNextFreeId(), PointerType.Mouse, true);
+            return new PointerPressedEventArgs(
+                source,
+                pointer,
+                source,
+                p,
+                0,
+                new PointerPointProperties(RawInputModifiers.None, PointerUpdateKind.LeftButtonPressed),
+                KeyModifiers.None);
+        }
     }
 }
diff --git a/tests/Avalonia.Controls.UnitTests/TextBoxTests.cs b/tests/Avalonia.Controls.UnitTests/TextBoxTests.cs
index 64c0020f92..cb20071860 100644
--- a/tests/Avalonia.Controls.UnitTests/TextBoxTests.cs
+++ b/tests/Avalonia.Controls.UnitTests/TextBoxTests.cs
@@ -8,6 +8,7 @@ using Avalonia.Controls.Templates;
 using Avalonia.Data;
 using Avalonia.Input;
 using Avalonia.Input.Platform;
+using Avalonia.Layout;
 using Avalonia.Media;
 using Avalonia.Platform;
 using Avalonia.UnitTests;
@@ -556,6 +557,31 @@ namespace Avalonia.Controls.UnitTests
                 Assert.True(true);
             }
         }
+        
+        [Theory]
+        [InlineData(Key.Up)]
+        [InlineData(Key.Down)]
+        [InlineData(Key.Home)]
+        [InlineData(Key.End)]
+        public void Textbox_doesnt_crash_when_Receives_input_and_template_not_applied(Key key)
+        {
+            using (UnitTestApplication.Start(FocusServices))
+            {
+                var target1 = new TextBox
+                {
+                    Template = CreateTemplate(),
+                    Text = "1234",
+                    IsVisible = false
+                };
+
+                var root = new TestRoot { Child = target1 };
+
+                target1.Focus();
+                Assert.True(target1.IsFocused);
+                
+                RaiseKeyEvent(target1, key, KeyModifiers.None);
+            }
+        }
 
         [Fact]
         public void TextBox_GotFocus_And_LostFocus_Work_Properly()
@@ -763,6 +789,9 @@ namespace Avalonia.Controls.UnitTests
             keyboardDevice: () => new KeyboardDevice(),
             keyboardNavigation: new KeyboardNavigationHandler(),
             inputManager: new InputManager(),
+            renderInterface: new MockPlatformRenderInterface(),
+            fontManagerImpl: new MockFontManagerImpl(),
+            textShaperImpl: new MockTextShaperImpl(),
             standardCursorFactory: Mock.Of<ICursorFactory>());
 
         private static TestServices Services => TestServices.MockThreadingInterface.With(
diff --git a/tests/Avalonia.Skia.UnitTests/Media/TextFormatting/TextFormatterTests.cs b/tests/Avalonia.Skia.UnitTests/Media/TextFormatting/TextFormatterTests.cs
index 9c2a1953f1..a19f97e74e 100644
--- a/tests/Avalonia.Skia.UnitTests/Media/TextFormatting/TextFormatterTests.cs
+++ b/tests/Avalonia.Skia.UnitTests/Media/TextFormatting/TextFormatterTests.cs
@@ -1,5 +1,6 @@
 using System;
 using System.Collections.Generic;
+using System.Linq;
 using Avalonia.Media;
 using Avalonia.Media.TextFormatting;
 using Avalonia.Media.TextFormatting.Unicode;
@@ -203,6 +204,40 @@ namespace Avalonia.Skia.UnitTests.Media.TextFormatting
                 Assert.Equal(expectedNumberOfLines, numberOfLines);
             }
         }
+        
+        [Fact]
+        public void Should_Wrap_RightToLeft()
+        {
+            using (Start())
+            {
+                const string text =
+                    "قطاعات الصناعة على الشبكة العالمية انترنيت ويونيكود، حيث ستتم، على الصعيدين الدولي والمحلي على حد سواء";
+                
+                var defaultProperties = new GenericTextRunProperties(Typeface.Default);
+
+                var textSource = new SingleBufferTextSource(text, defaultProperties);
+
+                var formatter = new TextFormatterImpl();
+
+                var currentTextSourceIndex = 0;
+
+                while (currentTextSourceIndex < text.Length)
+                {
+                    var textLine =
+                        formatter.FormatLine(textSource, currentTextSourceIndex, 50,
+                            new GenericTextParagraphProperties(defaultProperties, textWrap: TextWrapping.Wrap));
+
+                    var glyphClusters = textLine.TextRuns.Cast<ShapedTextCharacters>()
+                        .SelectMany(x => x.GlyphRun.GlyphClusters).ToArray();
+                
+                    Assert.True(glyphClusters[0] >= glyphClusters[^1]);
+                    
+                    Assert.Equal(currentTextSourceIndex, glyphClusters[^1]);
+
+                    currentTextSourceIndex += textLine.TextRange.Length;
+                }
+            }
+        }
 
         [InlineData("Whether to turn off HTTPS. This option only applies if Individual, " +
                     "IndividualB2C, SingleOrg, or MultiOrg aren't used for &#8209;&#8209;auth."
diff --git a/tests/Avalonia.Visuals.UnitTests/Rendering/SceneGraph/SceneBuilderTests.cs b/tests/Avalonia.Visuals.UnitTests/Rendering/SceneGraph/SceneBuilderTests.cs
index 42e573c8a5..e317b43efc 100644
--- a/tests/Avalonia.Visuals.UnitTests/Rendering/SceneGraph/SceneBuilderTests.cs
+++ b/tests/Avalonia.Visuals.UnitTests/Rendering/SceneGraph/SceneBuilderTests.cs
@@ -245,6 +245,34 @@ namespace Avalonia.Visuals.UnitTests.Rendering.SceneGraph
             }
         }
 
+        [Fact]
+        public void Should_Respect_Uniform_ZIndex()
+        {
+            using (UnitTestApplication.Start(TestServices.MockPlatformRenderInterface))
+            {
+                Panel panel;
+
+                var tree = new TestRoot
+                {
+                    Child = panel = new Panel()
+                };
+
+                for (var i = 0; i < 128; i++)
+                {
+                    panel.Children.Add(new Border());
+                }
+
+                var result = new Scene(tree);
+                var sceneBuilder = new SceneBuilder();
+                sceneBuilder.UpdateAll(result);
+
+                var panelNode = result.FindNode(tree.Child);
+                var expected = panel.Children.ToArray();
+                var actual = panelNode.Children.OfType<IVisualNode>().Select(x => x.Visual).ToArray();
+                Assert.Equal(expected, actual);
+            }
+        }
+
         [Fact]
         public void ClipBounds_Should_Be_In_Global_Coordinates()
         {