diff --git a/native/Avalonia.Native/src/OSX/AvnPanelWindow.mm b/native/Avalonia.Native/src/OSX/AvnPanelWindow.mm
index 2365189010..b49005de8a 100644
--- a/native/Avalonia.Native/src/OSX/AvnPanelWindow.mm
+++ b/native/Avalonia.Native/src/OSX/AvnPanelWindow.mm
@@ -3,8 +3,6 @@
 // Copyright (c) 2022 Avalonia. All rights reserved.
 //
 
-#pragma once
-
 #define IS_NSPANEL
 
 #include "AvnWindow.mm"
diff --git a/native/Avalonia.Native/src/OSX/AvnView.mm b/native/Avalonia.Native/src/OSX/AvnView.mm
index 02526afbcb..5436ad22f3 100644
--- a/native/Avalonia.Native/src/OSX/AvnView.mm
+++ b/native/Avalonia.Native/src/OSX/AvnView.mm
@@ -222,7 +222,7 @@
 
 - (void)mouseEvent:(NSEvent *)event withType:(AvnRawMouseEventType) type
 {
-    bool triggerInputWhenDisabled = type != Move;
+    bool triggerInputWhenDisabled = type != Move && type != LeaveWindow;
 
     if([self ignoreUserInput: triggerInputWhenDisabled])
     {
@@ -709,4 +709,4 @@
     return [[self accessibilityChild] accessibilityFocusedUIElement];
 }
 
-@end
\ No newline at end of file
+@end
diff --git a/native/Avalonia.Native/src/OSX/AvnWindow.mm b/native/Avalonia.Native/src/OSX/AvnWindow.mm
index f51c693777..9fc7ec4fec 100644
--- a/native/Avalonia.Native/src/OSX/AvnWindow.mm
+++ b/native/Avalonia.Native/src/OSX/AvnWindow.mm
@@ -68,7 +68,7 @@
     }
 }
 
-- (void)performClose:(id)sender
+- (void)performClose:(id _Nullable )sender
 {
     if([[self delegate] respondsToSelector:@selector(windowShouldClose:)])
     {
@@ -147,7 +147,7 @@
     }
 }
 
--(void) applyMenu:(AvnMenu *)menu
+-(void) applyMenu:(AvnMenu *_Nullable)menu
 {
     if(menu == nullptr)
     {
@@ -157,7 +157,7 @@
     _menu = menu;
 }
 
--(CLASS_NAME*)  initWithParent: (WindowBaseImpl*) parent contentRect: (NSRect)contentRect styleMask: (NSWindowStyleMask)styleMask;
+-(CLASS_NAME*_Nonnull)  initWithParent: (WindowBaseImpl*_Nonnull) parent contentRect: (NSRect)contentRect styleMask: (NSWindowStyleMask)styleMask;
 {
     // https://jameshfisher.com/2020/07/10/why-is-the-contentrect-of-my-nswindow-ignored/
     // create nswindow with specific contentRect, otherwise we wont be able to resize the window
@@ -176,14 +176,15 @@
 
     _isExtended = false;
 
-#ifdef IS_NSPANEL
-    [self setCollectionBehavior:NSWindowCollectionBehaviorCanJoinAllSpaces|NSWindowCollectionBehaviorFullScreenAuxiliary];
-#endif
+    if(self.isDialog)
+    {
+        [self setCollectionBehavior:NSWindowCollectionBehaviorCanJoinAllSpaces|NSWindowCollectionBehaviorFullScreenAuxiliary];
+    }
 
     return self;
 }
 
-- (BOOL)windowShouldClose:(NSWindow *)sender
+- (BOOL)windowShouldClose:(NSWindow *_Nonnull)sender
 {
     auto window = dynamic_cast<WindowImpl*>(_parent.getRaw());
 
@@ -195,21 +196,28 @@
     return true;
 }
 
-- (void)windowDidChangeBackingProperties:(NSNotification *)notification
+- (void)windowDidChangeBackingProperties:(NSNotification *_Nonnull)notification
 {
     [self backingScaleFactor];
 }
 
 
 
-- (void)windowWillClose:(NSNotification *)notification
+- (void)windowWillClose:(NSNotification *_Nonnull)notification
 {
     _closed = true;
     if(_parent)
     {
         ComPtr<WindowBaseImpl> parent = _parent;
         _parent = NULL;
-        [self restoreParentWindow];
+        
+        auto window = dynamic_cast<WindowImpl*>(parent.getRaw());
+        
+        if(window != nullptr)
+        {
+            window->SetParent(nullptr);
+        }
+        
         parent->BaseEvents->Closed();
         [parent->View onClosed];
     }
@@ -220,17 +228,11 @@
     if(_canBecomeKeyWindow)
     {
         // If the window has a child window being shown as a dialog then don't allow it to become the key window.
-        for(NSWindow* uch in [self childWindows])
+        auto parent = dynamic_cast<WindowImpl*>(_parent.getRaw());
+        
+        if(parent != nullptr)
         {
-            if (![uch conformsToProtocol:@protocol(AvnWindowProtocol)])
-            {
-                continue;
-            }
-
-            id <AvnWindowProtocol> ch = (id <AvnWindowProtocol>) uch;
-
-            if(ch.isDialog)
-                return false;
+            return parent->CanBecomeKeyWindow();
         }
 
         return true;
@@ -259,6 +261,10 @@
 -(void) setEnabled:(bool)enable
 {
     _isEnabled = enable;
+    
+    [[self standardWindowButton:NSWindowCloseButton] setEnabled:enable];
+    [[self standardWindowButton:NSWindowMiniaturizeButton] setEnabled:enable];
+    [[self standardWindowButton:NSWindowZoomButton] setEnabled:enable];
 }
 
 -(void)becomeKeyWindow
@@ -273,17 +279,12 @@
     [super becomeKeyWindow];
 }
 
--(void) restoreParentWindow;
+- (void)windowDidBecomeKey:(NSNotification *_Nonnull)notification
 {
-    auto parent = [self parentWindow];
-
-    if(parent != nil)
-    {
-        [parent removeChildWindow:self];
-    }
+    _parent->BringToFront();
 }
 
-- (void)windowDidMiniaturize:(NSNotification *)notification
+- (void)windowDidMiniaturize:(NSNotification *_Nonnull)notification
 {
     auto parent = dynamic_cast<IWindowStateChanged*>(_parent.operator->());
 
@@ -293,7 +294,7 @@
     }
 }
 
-- (void)windowDidDeminiaturize:(NSNotification *)notification
+- (void)windowDidDeminiaturize:(NSNotification *_Nonnull)notification
 {
     auto parent = dynamic_cast<IWindowStateChanged*>(_parent.operator->());
 
@@ -303,7 +304,7 @@
     }
 }
 
-- (void)windowDidResize:(NSNotification *)notification
+- (void)windowDidResize:(NSNotification *_Nonnull)notification
 {
     auto parent = dynamic_cast<IWindowStateChanged*>(_parent.operator->());
 
@@ -313,7 +314,7 @@
     }
 }
 
-- (void)windowWillExitFullScreen:(NSNotification *)notification
+- (void)windowWillExitFullScreen:(NSNotification *_Nonnull)notification
 {
     auto parent = dynamic_cast<IWindowStateChanged*>(_parent.operator->());
 
@@ -323,7 +324,7 @@
     }
 }
 
-- (void)windowDidExitFullScreen:(NSNotification *)notification
+- (void)windowDidExitFullScreen:(NSNotification *_Nonnull)notification
 {
     auto parent = dynamic_cast<IWindowStateChanged*>(_parent.operator->());
 
@@ -346,7 +347,7 @@
     }
 }
 
-- (void)windowWillEnterFullScreen:(NSNotification *)notification
+- (void)windowWillEnterFullScreen:(NSNotification *_Nonnull)notification
 {
     auto parent = dynamic_cast<IWindowStateChanged*>(_parent.operator->());
 
@@ -356,7 +357,7 @@
     }
 }
 
-- (void)windowDidEnterFullScreen:(NSNotification *)notification
+- (void)windowDidEnterFullScreen:(NSNotification *_Nonnull)notification
 {
     auto parent = dynamic_cast<IWindowStateChanged*>(_parent.operator->());
 
@@ -367,7 +368,7 @@
     }
 }
 
-- (BOOL)windowShouldZoom:(NSWindow *)window toFrame:(NSRect)newFrame
+- (BOOL)windowShouldZoom:(NSWindow *_Nonnull)window toFrame:(NSRect)newFrame
 {
     return true;
 }
@@ -378,11 +379,13 @@
         _parent->BaseEvents->Deactivated();
 
     [self showAppMenuOnly];
+    
+    [self invalidateShadow];
 
     [super resignKeyWindow];
 }
 
-- (void)windowDidMove:(NSNotification *)notification
+- (void)windowDidMove:(NSNotification *_Nonnull)notification
 {
     AvnPoint position;
 
@@ -414,7 +417,7 @@
     return pt;
 }
 
-- (void)sendEvent:(NSEvent *)event
+- (void)sendEvent:(NSEvent *_Nonnull)event
 {
     [super sendEvent:event];
 
@@ -437,8 +440,10 @@
 
                     _parent->BaseEvents->RawMouseEvent(NonClientLeftButtonDown, static_cast<uint32>([event timestamp] * 1000), AvnInputModifiersNone, point, delta);
                 }
+                
+                _parent->BringToFront();
             }
-                break;
+            break;
 
             case NSEventTypeMouseEntered:
             {
diff --git a/native/Avalonia.Native/src/OSX/INSWindowHolder.h b/native/Avalonia.Native/src/OSX/INSWindowHolder.h
index ae64a53e7d..3c5010966b 100644
--- a/native/Avalonia.Native/src/OSX/INSWindowHolder.h
+++ b/native/Avalonia.Native/src/OSX/INSWindowHolder.h
@@ -11,7 +11,7 @@
 struct INSWindowHolder
 {
     virtual NSWindow* _Nonnull GetNSWindow () = 0;
-    virtual NSView* _Nonnull GetNSView () = 0;
+    virtual AvnView* _Nonnull GetNSView () = 0;
 };
 
 #endif //AVALONIA_NATIVE_OSX_INSWINDOWHOLDER_H
diff --git a/native/Avalonia.Native/src/OSX/WindowBaseImpl.h b/native/Avalonia.Native/src/OSX/WindowBaseImpl.h
index 83850e780c..040ba39b6d 100644
--- a/native/Avalonia.Native/src/OSX/WindowBaseImpl.h
+++ b/native/Avalonia.Native/src/OSX/WindowBaseImpl.h
@@ -26,7 +26,7 @@ BEGIN_INTERFACE_MAP()
 
     virtual ~WindowBaseImpl();
 
-    WindowBaseImpl(IAvnWindowBaseEvents *events, IAvnGlContext *gl);
+    WindowBaseImpl(IAvnWindowBaseEvents *events, IAvnGlContext *gl, bool usePanel = false);
 
     virtual HRESULT ObtainNSWindowHandle(void **ret) override;
 
@@ -38,7 +38,7 @@ BEGIN_INTERFACE_MAP()
 
     virtual NSWindow *GetNSWindow() override;
 
-    virtual NSView *GetNSView() override;
+    virtual AvnView *GetNSView() override;
 
     virtual HRESULT Show(bool activate, bool isDialog) override;
 
@@ -99,6 +99,8 @@ BEGIN_INTERFACE_MAP()
     virtual bool IsDialog();
 
     id<AvnWindowProtocol> GetWindowProtocol ();
+                           
+    virtual void BringToFront ();
 
 protected:
     virtual NSWindowStyleMask GetStyle();
diff --git a/native/Avalonia.Native/src/OSX/WindowBaseImpl.mm b/native/Avalonia.Native/src/OSX/WindowBaseImpl.mm
index 6dc59ae4d8..c420736b46 100644
--- a/native/Avalonia.Native/src/OSX/WindowBaseImpl.mm
+++ b/native/Avalonia.Native/src/OSX/WindowBaseImpl.mm
@@ -21,7 +21,7 @@ WindowBaseImpl::~WindowBaseImpl() {
     Window = nullptr;
 }
 
-WindowBaseImpl::WindowBaseImpl(IAvnWindowBaseEvents *events, IAvnGlContext *gl) {
+WindowBaseImpl::WindowBaseImpl(IAvnWindowBaseEvents *events, IAvnGlContext *gl, bool usePanel) {
     _shown = false;
     _inResize = false;
     BaseEvents = events;
@@ -36,8 +36,10 @@ WindowBaseImpl::WindowBaseImpl(IAvnWindowBaseEvents *events, IAvnGlContext *gl)
     lastMaxSize = NSSize { CGFLOAT_MAX, CGFLOAT_MAX};
     lastMinSize = NSSize { 0, 0 };
 
-    Window = nullptr;
     lastMenu = nullptr;
+    
+    CreateNSWindow(usePanel);
+    InitialiseNSWindow();
 }
 
 HRESULT WindowBaseImpl::ObtainNSViewHandle(void **ret) {
@@ -68,7 +70,7 @@ NSWindow *WindowBaseImpl::GetNSWindow() {
     return Window;
 }
 
-NSView *WindowBaseImpl::GetNSView() {
+AvnView *WindowBaseImpl::GetNSView() {
     return View;
 }
 
@@ -88,7 +90,6 @@ HRESULT WindowBaseImpl::Show(bool activate, bool isDialog) {
     START_COM_CALL;
 
     @autoreleasepool {
-        CreateNSWindow(isDialog);
         InitialiseNSWindow();
 
         if(hasPosition)
@@ -143,8 +144,6 @@ HRESULT WindowBaseImpl::Hide() {
     @autoreleasepool {
         if (Window != nullptr) {
             [Window orderOut:Window];
-
-            [GetWindowProtocol() restoreParentWindow];
         }
 
         return S_OK;
@@ -558,6 +557,8 @@ void WindowBaseImpl::CreateNSWindow(bool isDialog) {
             CleanNSWindow();
 
             Window = [[AvnPanel alloc] initWithParent:this contentRect:NSRect{0, 0, lastSize} styleMask:GetStyle()];
+            
+            [Window setHidesOnDeactivate:false];
         }
     } else {
         if (![Window isKindOfClass:[AvnWindow class]]) {
@@ -585,6 +586,7 @@ void WindowBaseImpl::InitialiseNSWindow() {
 
         [Window setOpaque:false];
         
+        [Window setHasShadow:true];
         [Window invalidateShadow];
 
         if (lastMenu != nullptr) {
@@ -608,6 +610,11 @@ id <AvnWindowProtocol> WindowBaseImpl::GetWindowProtocol() {
     return (id <AvnWindowProtocol>) Window;
 }
 
+void WindowBaseImpl::BringToFront()
+{
+    // do nothing.
+}
+
 extern IAvnWindow* CreateAvnWindow(IAvnWindowEvents*events, IAvnGlContext* gl)
 {
     @autoreleasepool
diff --git a/native/Avalonia.Native/src/OSX/WindowImpl.h b/native/Avalonia.Native/src/OSX/WindowImpl.h
index db19497b29..76d5cbf6ea 100644
--- a/native/Avalonia.Native/src/OSX/WindowImpl.h
+++ b/native/Avalonia.Native/src/OSX/WindowImpl.h
@@ -8,6 +8,7 @@
 
 #import "WindowBaseImpl.h"
 #include "IWindowStateChanged.h"
+#include <list>
 
 class WindowImpl : public virtual WindowBaseImpl, public virtual IAvnWindow, public IWindowStateChanged
 {
@@ -22,6 +23,8 @@ private:
     bool _transitioningWindowState;
     bool _isClientAreaExtended;
     bool _isDialog;
+    WindowImpl* _parent;
+    std::list<WindowImpl*> _children;
     AvnExtendClientAreaChromeHints _extendClientHints;
 
     FORWARD_IUNKNOWN()
@@ -90,6 +93,10 @@ BEGIN_INTERFACE_MAP()
     virtual bool IsDialog() override;
     
     virtual void OnInitialiseNSWindow() override;
+    
+    virtual void BringToFront () override;
+    
+    bool CanBecomeKeyWindow ();
 
 protected:
     virtual NSWindowStyleMask GetStyle() override;
diff --git a/native/Avalonia.Native/src/OSX/WindowImpl.mm b/native/Avalonia.Native/src/OSX/WindowImpl.mm
index d96fe717ab..555e9dff9b 100644
--- a/native/Avalonia.Native/src/OSX/WindowImpl.mm
+++ b/native/Avalonia.Native/src/OSX/WindowImpl.mm
@@ -10,6 +10,7 @@
 #include "WindowProtocol.h"
 
 WindowImpl::WindowImpl(IAvnWindowEvents *events, IAvnGlContext *gl) : WindowBaseImpl(events, gl) {
+    _children = std::list<WindowImpl*>();
     _isClientAreaExtended = false;
     _extendClientHints = AvnDefaultChrome;
     _fullScreenActive = false;
@@ -20,6 +21,7 @@ WindowImpl::WindowImpl(IAvnWindowEvents *events, IAvnGlContext *gl) : WindowBase
     _lastWindowState = Normal;
     _actualWindowState = Normal;
     _lastTitle = @"";
+    _parent = nullptr;
     WindowEvents = events;
 }
 
@@ -28,24 +30,12 @@ void WindowImpl::HideOrShowTrafficLights() {
         return;
     }
 
-    for (id subview in Window.contentView.superview.subviews) {
-        if ([subview isKindOfClass:NSClassFromString(@"NSTitlebarContainerView")]) {
-            NSView *titlebarView = [subview subviews][0];
-            for (id button in titlebarView.subviews) {
-                if ([button isKindOfClass:[NSButton class]]) {
-                    if (_isClientAreaExtended) {
-                        auto wantsChrome = (_extendClientHints & AvnSystemChrome) || (_extendClientHints & AvnPreferSystemChrome);
-
-                        [button setHidden:!wantsChrome];
-                    } else {
-                        [button setHidden:(_decorations != SystemDecorationsFull)];
-                    }
-
-                    [button setWantsLayer:true];
-                }
-            }
-        }
-    }
+    bool wantsChrome = (_extendClientHints & AvnSystemChrome) || (_extendClientHints & AvnPreferSystemChrome);
+    bool hasTrafficLights = _isClientAreaExtended ? !wantsChrome : _decorations != SystemDecorationsFull;
+    
+    [[Window standardWindowButton:NSWindowCloseButton] setHidden:hasTrafficLights];
+    [[Window standardWindowButton:NSWindowMiniaturizeButton] setHidden:hasTrafficLights];
+    [[Window standardWindowButton:NSWindowZoomButton] setHidden:hasTrafficLights];
 }
 
 void WindowImpl::OnInitialiseNSWindow(){
@@ -61,6 +51,11 @@ void WindowImpl::OnInitialiseNSWindow(){
         [GetWindowProtocol() setIsExtended:true];
         SetExtendClientArea(true);
     }
+    
+    if(_parent != nullptr)
+    {
+        SetParent(_parent);
+    }
 }
 
 HRESULT WindowImpl::Show(bool activate, bool isDialog) {
@@ -90,26 +85,68 @@ HRESULT WindowImpl::SetParent(IAvnWindow *parent) {
     START_COM_CALL;
 
     @autoreleasepool {
-        if (parent == nullptr)
-            return E_POINTER;
+        if(_parent != nullptr)
+        {
+            _parent->_children.remove(this);
+            auto parent = _parent;
+            
+            dispatch_async(dispatch_get_main_queue(), ^{
+                parent->BringToFront();
+            });
+        }
 
         auto cparent = dynamic_cast<WindowImpl *>(parent);
-        if (cparent == nullptr)
-            return E_INVALIDARG;
-
-        // If one tries to show a child window with a minimized parent window, then the parent window will be
-        // restored but macOS isn't kind enough to *tell* us that, so the window will be left in a non-interactive
-        // state. Detect this and explicitly restore the parent window ourselves to avoid this situation.
-        if (cparent->WindowState() == Minimized)
-            cparent->SetWindowState(Normal);
+        
+        _parent = cparent;
+        
+        if(_parent != nullptr && Window != nullptr){
+            // If one tries to show a child window with a minimized parent window, then the parent window will be
+            // restored but macOS isn't kind enough to *tell* us that, so the window will be left in a non-interactive
+            // state. Detect this and explicitly restore the parent window ourselves to avoid this situation.
+            if (cparent->WindowState() == Minimized)
+                cparent->SetWindowState(Normal);
+
+            [Window setCollectionBehavior:NSWindowCollectionBehaviorFullScreenAuxiliary];
+                
+            cparent->_children.push_back(this);
+                
+            UpdateStyle();
+        }
 
-        [Window setCollectionBehavior:NSWindowCollectionBehaviorFullScreenAuxiliary];
-        [cparent->Window addChildWindow:Window ordered:NSWindowAbove];
+        return S_OK;
+    }
+}
 
-        UpdateStyle();
+void WindowImpl::BringToFront()
+{
+    if(IsDialog())
+    {
+        Activate();
+    }
+    else
+    {
+        [Window orderFront:nullptr];
+    }
+    
+    [Window invalidateShadow];
+    
+    for(auto iterator = _children.begin(); iterator != _children.end(); iterator++)
+    {
+        (*iterator)->BringToFront();
+    }
+}
 
-        return S_OK;
+bool WindowImpl::CanBecomeKeyWindow()
+{
+    for(auto iterator = _children.begin(); iterator != _children.end(); iterator++)
+    {
+        if((*iterator)->IsDialog())
+        {
+            return false;
+        }
     }
+    
+    return true;
 }
 
 void WindowImpl::StartStateTransition() {
@@ -523,7 +560,7 @@ bool WindowImpl::IsDialog() {
 }
 
 NSWindowStyleMask WindowImpl::GetStyle() {
-    unsigned long s = this->_isDialog ? NSWindowStyleMaskDocModalWindow : NSWindowStyleMaskBorderless;
+    unsigned long s = NSWindowStyleMaskBorderless;
 
     switch (_decorations) {
         case SystemDecorationsNone:
@@ -535,7 +572,7 @@ NSWindowStyleMask WindowImpl::GetStyle() {
             break;
 
         case SystemDecorationsFull:
-            s = s | NSWindowStyleMaskTitled | NSWindowStyleMaskClosable | NSWindowStyleMaskBorderless;
+            s = s | NSWindowStyleMaskTitled | NSWindowStyleMaskClosable;
 
             if (_canResize) {
                 s = s | NSWindowStyleMaskResizable;
@@ -543,7 +580,7 @@ NSWindowStyleMask WindowImpl::GetStyle() {
             break;
     }
 
-    if ([Window parentWindow] == nullptr) {
+    if (!IsDialog()) {
         s |= NSWindowStyleMaskMiniaturizable;
     }
 
diff --git a/native/Avalonia.Native/src/OSX/WindowProtocol.h b/native/Avalonia.Native/src/OSX/WindowProtocol.h
index 0e5c5869e7..cb5f86bdb9 100644
--- a/native/Avalonia.Native/src/OSX/WindowProtocol.h
+++ b/native/Avalonia.Native/src/OSX/WindowProtocol.h
@@ -11,7 +11,6 @@
 
 @protocol AvnWindowProtocol
 -(void) pollModalSession: (NSModalSession _Nonnull) session;
--(void) restoreParentWindow;
 -(bool) shouldTryToHandleEvents;
 -(void) setEnabled: (bool) enable;
 -(void) showAppMenuOnly;
diff --git a/samples/ControlCatalog/Pages/DialogsPage.xaml b/samples/ControlCatalog/Pages/DialogsPage.xaml
index 6ac9dcfe22..8a835867b3 100644
--- a/samples/ControlCatalog/Pages/DialogsPage.xaml
+++ b/samples/ControlCatalog/Pages/DialogsPage.xaml
@@ -20,7 +20,7 @@
                  Text="Window dialogs" />
       <Button Name="DecoratedWindow">Decorated _window</Button>
       <Button Name="DecoratedWindowDialog">Decorated w_indow (dialog)</Button>
-      <Button Name="Dialog">_Dialog</Button>
+      <Button Name="Dialog" ToolTip.Tip="Shows a dialog">_Dialog</Button>
       <Button Name="DialogNoTaskbar">Dialog (_No taskbar icon)</Button>
       <Button Name="OwnedWindow">Own_ed window</Button>
       <Button Name="OwnedWindowNoTaskbar">Owned window (No tas_kbar icon)</Button>
diff --git a/samples/ControlCatalog/Pages/DialogsPage.xaml.cs b/samples/ControlCatalog/Pages/DialogsPage.xaml.cs
index bed9f4c62a..1853c83365 100644
--- a/samples/ControlCatalog/Pages/DialogsPage.xaml.cs
+++ b/samples/ControlCatalog/Pages/DialogsPage.xaml.cs
@@ -151,6 +151,7 @@ namespace ControlCatalog.Pages
         private Window CreateSampleWindow()
         {
             Button button;
+            Button dialogButton;
             
             var window = new Window
             {
@@ -167,6 +168,12 @@ namespace ControlCatalog.Pages
                             HorizontalAlignment = HorizontalAlignment.Center,
                             Content = "Click to close",
                             IsDefault = true
+                        }),
+                        (dialogButton = new Button
+                        {
+                            HorizontalAlignment = HorizontalAlignment.Center,
+                            Content = "Dialog",
+                            IsDefault = false
                         })
                     }
                 },
@@ -174,6 +181,12 @@ namespace ControlCatalog.Pages
             };
 
             button.Click += (_, __) => window.Close();
+            dialogButton.Click += (_, __) =>
+            {
+                var dialog = CreateSampleWindow();
+                dialog.Height = 200;
+                dialog.ShowDialog(window);
+            };
 
             return window;
         }
diff --git a/src/Avalonia.Base/Data/Converters/DefaultValueConverter.cs b/src/Avalonia.Base/Data/Converters/DefaultValueConverter.cs
index 11d50afe93..c4f4362537 100644
--- a/src/Avalonia.Base/Data/Converters/DefaultValueConverter.cs
+++ b/src/Avalonia.Base/Data/Converters/DefaultValueConverter.cs
@@ -33,7 +33,14 @@ namespace Avalonia.Data.Converters
 
             if (typeof(ICommand).IsAssignableFrom(targetType) && value is Delegate d && d.Method.GetParameters().Length <= 1)
             {
-                return new MethodToCommandConverter(d);
+                if (d.Method.IsPrivate == false)
+                {
+                    return new MethodToCommandConverter(d);
+                }
+                else
+                {
+                    return new BindingNotification(new InvalidCastException("You can't bind to private methods!"), BindingErrorType.Error);
+                }
             }
 
             if (TypeUtilities.TryConvert(targetType, value, culture, out var result))
diff --git a/src/Avalonia.Controls/ContextMenu.cs b/src/Avalonia.Controls/ContextMenu.cs
index 2b122d4174..7b35e35278 100644
--- a/src/Avalonia.Controls/ContextMenu.cs
+++ b/src/Avalonia.Controls/ContextMenu.cs
@@ -450,6 +450,11 @@ namespace Avalonia.Controls
             if (sender is Control control
                 && control.ContextMenu is ContextMenu contextMenu)
             {
+                if (contextMenu._popup?.Parent == control)
+                {
+                    ((ISetLogicalParent)contextMenu._popup).SetParent(null);
+                }
+
                 contextMenu.Close();
             }
         }
diff --git a/src/Avalonia.Controls/Flyouts/FlyoutBase.cs b/src/Avalonia.Controls/Flyouts/FlyoutBase.cs
index d024f86b32..dfbd3f9a36 100644
--- a/src/Avalonia.Controls/Flyouts/FlyoutBase.cs
+++ b/src/Avalonia.Controls/Flyouts/FlyoutBase.cs
@@ -175,7 +175,8 @@ namespace Avalonia.Controls.Primitives
 
             IsOpen = false;
             Popup.IsOpen = false;
-
+            ((ISetLogicalParent)Popup).SetParent(null);
+            
             // Ensure this isn't active
             _transientDisposable?.Dispose();
             _transientDisposable = null;
diff --git a/tests/Avalonia.Controls.UnitTests/ContextMenuTests.cs b/tests/Avalonia.Controls.UnitTests/ContextMenuTests.cs
index ba01f3db40..b63cbd286e 100644
--- a/tests/Avalonia.Controls.UnitTests/ContextMenuTests.cs
+++ b/tests/Avalonia.Controls.UnitTests/ContextMenuTests.cs
@@ -446,6 +446,27 @@ namespace Avalonia.Controls.UnitTests
             }
         }
 
+        [Fact]
+        public void Should_Reset_Popup_Parent_On_Target_Detached()
+        {
+            using (Application())
+            {
+                var userControl = new UserControl();
+                var window = PreparedWindow(userControl);
+                window.Show();
+                
+                var menu = new ContextMenu();
+                userControl.ContextMenu = menu;
+                menu.Open();
+                
+                var popup = Assert.IsType<Popup>(menu.Parent);
+                Assert.NotNull(popup.Parent);
+                
+                window.Content = null;
+                Assert.Null(popup.Parent);
+            }
+        }
+
         [Fact]
         public void Context_Menu_In_Resources_Can_Be_Shared()
         {
diff --git a/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs b/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs
index c2dd8cf01a..8b77074960 100644
--- a/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs
+++ b/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs
@@ -432,6 +432,26 @@ namespace Avalonia.Controls.UnitTests
             }
         }
 
+        [Fact]
+        public void Should_Reset_Popup_Parent_On_Target_Detached()
+        {
+            using (CreateServicesWithFocus())
+            {
+                var userControl = new UserControl();
+                var window = PreparedWindow(userControl);
+                window.Show();
+                
+                var flyout = new TestFlyout();
+                flyout.ShowAt(userControl);
+                
+                var popup = Assert.IsType<Popup>(flyout.Popup);
+                Assert.NotNull(popup.Parent);
+                
+                window.Content = null;
+                Assert.Null(popup.Parent);
+            }
+        }
+
         [Fact]
         public void ContextFlyout_Can_Be_Set_In_Styles()
         {
@@ -549,5 +569,10 @@ namespace Avalonia.Controls.UnitTests
                 new PointerPointProperties(RawInputModifiers.None, PointerUpdateKind.LeftButtonPressed),
                 KeyModifiers.None);
         }
+        
+        public class TestFlyout : Flyout
+        {
+            public new Popup Popup => base.Popup;
+        }
     }
 }
diff --git a/tests/Avalonia.Markup.UnitTests/Data/BindingTests_Method.cs b/tests/Avalonia.Markup.UnitTests/Data/BindingTests_Method.cs
new file mode 100644
index 0000000000..e613a178d5
--- /dev/null
+++ b/tests/Avalonia.Markup.UnitTests/Data/BindingTests_Method.cs
@@ -0,0 +1,32 @@
+using Avalonia.Controls;
+using Avalonia.Data;
+using Avalonia.Input;
+using Avalonia.Interactivity;
+using Xunit;
+
+namespace Avalonia.Markup.UnitTests.Data
+{
+    public class BindingTests_Method
+    {
+        [Fact]
+        public void Binding_To_Private_Methods_Shouldnt_Work()
+        {
+            var vm = new TestClass();
+            var target = new Button
+            {
+                DataContext = vm,
+                [!Button.CommandProperty] = new Binding("MyMethod"),
+            };
+            target.RaiseEvent(new RoutedEventArgs(AccessKeyHandler.AccessKeyPressedEvent));
+
+            Assert.False(vm.IsSet);
+        }
+
+
+        class TestClass
+        {
+            public bool IsSet { get; set; }
+            private void MyMethod() => IsSet = true;
+        }
+    }
+}