diff --git a/samples/ControlCatalog/App.xaml b/samples/ControlCatalog/App.xaml
index d0e1bd885e4..fab46223035 100644
--- a/samples/ControlCatalog/App.xaml
+++ b/samples/ControlCatalog/App.xaml
@@ -43,6 +43,7 @@
                 <NativeMenuItemSeparator />
                 <NativeMenuItem Header="Option 3" ToggleType="CheckBox" IsChecked="True" Command="{Binding ToggleCommand}" />
                 <NativeMenuItem Icon="/Assets/test_icon.ico" Header="Restore Defaults" Command="{Binding ToggleCommand}" />
+                <NativeMenuItem Header="Disabled option" IsEnabled="False" />
               </NativeMenu>
             </NativeMenuItem>
             <NativeMenuItem Header="Exit" Command="{Binding ExitCommand}" />
diff --git a/src/Avalonia.Controls/TrayIcon.cs b/src/Avalonia.Controls/TrayIcon.cs
index ad4f2006157..3c63a29ad69 100644
--- a/src/Avalonia.Controls/TrayIcon.cs
+++ b/src/Avalonia.Controls/TrayIcon.cs
@@ -63,6 +63,10 @@ static TrayIcon()
                         args.NewValue.Value.CollectionChanged += Icons_CollectionChanged;
                     }
                 }
+                else
+                {
+                    throw new InvalidOperationException("TrayIcon.Icons must be set on the Application.");
+                }
             });
 
             var app = Application.Current ?? throw new InvalidOperationException("Application not yet initialized.");
@@ -125,9 +129,9 @@ public static readonly StyledProperty<NativeMenu?> MenuProperty
         public static readonly StyledProperty<bool> IsVisibleProperty =
             Visual.IsVisibleProperty.AddOwner<TrayIcon>();
 
-        public static void SetIcons(AvaloniaObject o, TrayIcons trayIcons) => o.SetValue(IconsProperty, trayIcons);
+        public static void SetIcons(Application o, TrayIcons trayIcons) => o.SetValue(IconsProperty, trayIcons);
 
-        public static TrayIcons GetIcons(AvaloniaObject o) => o.GetValue(IconsProperty);
+        public static TrayIcons GetIcons(Application o) => o.GetValue(IconsProperty);
         
         /// <summary>
         /// Gets or sets the <see cref="Command"/> property of a TrayIcon.
diff --git a/src/Avalonia.Themes.Default/NativeMenuBar.xaml b/src/Avalonia.Themes.Default/NativeMenuBar.xaml
index c5d7ad55d70..9d004e3f7e1 100644
--- a/src/Avalonia.Themes.Default/NativeMenuBar.xaml
+++ b/src/Avalonia.Themes.Default/NativeMenuBar.xaml
@@ -13,6 +13,7 @@
         <Menu.Styles>
           <Style Selector="MenuItem">
             <Setter Property="Header" Value="{Binding Header}"/>
+            <Setter Property="IsEnabled" Value="{Binding IsEnabled}"/>
             <Setter Property="InputGesture" Value="{Binding Gesture}"/>
             <Setter Property="Items" Value="{Binding Menu.Items}"/>
             <Setter Property="Command" Value="{Binding Command}"/>
diff --git a/src/Avalonia.Themes.Fluent/Controls/NativeMenuBar.xaml b/src/Avalonia.Themes.Fluent/Controls/NativeMenuBar.xaml
index 7860e08ef5b..85eb64a9e0a 100644
--- a/src/Avalonia.Themes.Fluent/Controls/NativeMenuBar.xaml
+++ b/src/Avalonia.Themes.Fluent/Controls/NativeMenuBar.xaml
@@ -14,6 +14,7 @@
         <Menu.Styles>
           <Style x:CompileBindings="False" Selector="MenuItem">
             <Setter Property="Header" Value="{Binding Header}"/>
+            <Setter Property="IsEnabled" Value="{Binding IsEnabled}"/>
             <Setter Property="InputGesture" Value="{Binding Gesture}"/>
             <Setter Property="Items" Value="{Binding Menu.Items}"/>
             <Setter Property="Command" Value="{Binding Command}"/>
diff --git a/src/Windows/Avalonia.Win32/IconImpl.cs b/src/Windows/Avalonia.Win32/IconImpl.cs
index 85488015558..4d2b89b0cc7 100644
--- a/src/Windows/Avalonia.Win32/IconImpl.cs
+++ b/src/Windows/Avalonia.Win32/IconImpl.cs
@@ -1,6 +1,5 @@
 using System;
 using System.Drawing;
-using System.Drawing.Imaging;
 using System.IO;
 using Avalonia.Platform;
 
@@ -8,31 +7,18 @@ namespace Avalonia.Win32
 {
     class IconImpl : IWindowIconImpl
     {
-        private Bitmap bitmap;
-        private Icon icon;
-
-        public IconImpl(Bitmap bitmap)
-        {
-            this.bitmap = bitmap;
-        }
+        private readonly Icon icon;
 
         public IconImpl(Icon icon)
         {
             this.icon = icon;
         }
 
-        public IntPtr HIcon => icon?.Handle ?? bitmap.GetHicon();
+        public IntPtr HIcon => icon.Handle;
 
         public void Save(Stream outputStream)
         {
-            if (icon != null)
-            {
-                icon.Save(outputStream);
-            }
-            else
-            {
-                bitmap.Save(outputStream, ImageFormat.Png);
-            }
+            icon.Save(outputStream);
         }
     }
 }
diff --git a/src/Windows/Avalonia.Win32/TrayIconImpl.cs b/src/Windows/Avalonia.Win32/TrayIconImpl.cs
index 86732539f12..f3a49f3249e 100644
--- a/src/Windows/Avalonia.Win32/TrayIconImpl.cs
+++ b/src/Windows/Avalonia.Win32/TrayIconImpl.cs
@@ -16,6 +16,8 @@ namespace Avalonia.Win32
 {
     public class TrayIconImpl : ITrayIconImpl
     {
+        private static readonly IntPtr s_emptyIcon = new System.Drawing.Bitmap(32, 32).GetHicon();
+        
         private readonly int _uniqueId;
         private static int s_nextUniqueId;
         private bool _iconAdded;
@@ -84,7 +86,7 @@ private void UpdateIcon(bool remove = false)
                 uID = _uniqueId,
                 uFlags = NIF.TIP | NIF.MESSAGE,
                 uCallbackMessage = (int)CustomWindowsMessage.WM_TRAYMOUSE,
-                hIcon = _icon?.HIcon ?? new IconImpl(new System.Drawing.Bitmap(32, 32)).HIcon,
+                hIcon = _icon?.HIcon ?? s_emptyIcon,
                 szTip = _tooltipText ?? ""
             };
 
diff --git a/src/Windows/Avalonia.Win32/Win32NativeToManagedMenuExporter.cs b/src/Windows/Avalonia.Win32/Win32NativeToManagedMenuExporter.cs
index da8357a6f18..2b8bf6f8bfb 100644
--- a/src/Windows/Avalonia.Win32/Win32NativeToManagedMenuExporter.cs
+++ b/src/Windows/Avalonia.Win32/Win32NativeToManagedMenuExporter.cs
@@ -1,7 +1,10 @@
 using System.Collections.Generic;
+using System.Reactive.Linq;
 using Avalonia.Collections;
 using Avalonia.Controls;
 using Avalonia.Controls.Platform;
+using Avalonia.Media.Imaging;
+using Avalonia.Utilities;
 
 #nullable enable
 
@@ -28,7 +31,16 @@ private AvaloniaList<MenuItem> Populate(NativeMenu nativeMenu)
                 }
                 else if (menuItem is NativeMenuItem item)
                 {
-                    var newItem = new MenuItem { Header = item.Header, Icon = item.Icon, Command = item.Command, CommandParameter = item.CommandParameter };
+                    var newItem = new MenuItem
+                    {
+                        [!MenuItem.HeaderProperty] = item.GetObservable(NativeMenuItem.HeaderProperty).ToBinding(),
+                        [!MenuItem.IconProperty] = item.GetObservable(NativeMenuItem.IconProperty)
+                            .Select(i => i is {} bitmap ? new Image { Source = bitmap } : null).ToBinding(),
+                        [!MenuItem.IsEnabledProperty] = item.GetObservable(NativeMenuItem.IsEnabledProperty).ToBinding(),
+                        [!MenuItem.CommandProperty] = item.GetObservable(NativeMenuItem.CommandProperty).ToBinding(),
+                        [!MenuItem.CommandParameterProperty] = item.GetObservable(NativeMenuItem.CommandParameterProperty).ToBinding(),
+                        [!MenuItem.InputGestureProperty] = item.GetObservable(NativeMenuItem.GestureProperty).ToBinding()
+                    };
 
                     if (item.Menu != null)
                     {
@@ -36,7 +48,7 @@ private AvaloniaList<MenuItem> Populate(NativeMenu nativeMenu)
                     }
                     else if (item.HasClickHandlers && item is INativeMenuItemExporterEventsImplBridge bridge)
                     {
-                        newItem.Click += (_, __) => bridge.RaiseClicked();
+                        newItem.Click += (_, _) => bridge.RaiseClicked();
                     }
 
                     result.Add(newItem);
diff --git a/src/Windows/Avalonia.Win32/Win32Platform.cs b/src/Windows/Avalonia.Win32/Win32Platform.cs
index eed2d2ee856..e89f9f65201 100644
--- a/src/Windows/Avalonia.Win32/Win32Platform.cs
+++ b/src/Windows/Avalonia.Win32/Win32Platform.cs
@@ -346,7 +346,7 @@ public IWindowIconImpl LoadIcon(IBitmapImpl bitmap)
             using (var memoryStream = new MemoryStream())
             {
                 bitmap.Save(memoryStream);
-                return new IconImpl(new System.Drawing.Bitmap(memoryStream));
+                return CreateIconImpl(memoryStream);
             }
         }
 
@@ -354,11 +354,15 @@ private static IconImpl CreateIconImpl(Stream stream)
         {
             try
             {
+                // new Icon() will work only if stream is an "ico" file.
                 return new IconImpl(new System.Drawing.Icon(stream));
             }
             catch (ArgumentException)
             {
-                return new IconImpl(new System.Drawing.Bitmap(stream));
+                // Fallback to Bitmap creation and converting into a windows icon. 
+                using var icon = new System.Drawing.Bitmap(stream);
+                var hIcon = icon.GetHicon();
+                return new IconImpl(System.Drawing.Icon.FromHandle(hIcon));
             }
         }