diff --git a/native/Avalonia.Native/src/OSX/AvnWindow.mm b/native/Avalonia.Native/src/OSX/AvnWindow.mm
index 53982ad4e7..d673523983 100644
--- a/native/Avalonia.Native/src/OSX/AvnWindow.mm
+++ b/native/Avalonia.Native/src/OSX/AvnWindow.mm
@@ -32,6 +32,7 @@
     bool _isEnabled;
     bool _canBecomeKeyWindow;
     bool _isExtended;
+    bool _isTransitioningToFullScreen;
     AvnMenu* _menu;
 }
 
@@ -174,6 +175,7 @@
     [self setBackgroundColor: [NSColor clearColor]];
 
     _isExtended = false;
+    _isTransitioningToFullScreen = false;
 
     if(self.isDialog)
     {
@@ -348,6 +350,7 @@
 
 - (void)windowWillEnterFullScreen:(NSNotification *_Nonnull)notification
 {
+    _isTransitioningToFullScreen = true;
     auto parent = dynamic_cast<IWindowStateChanged*>(_parent.operator->());
 
     if(parent != nullptr)
@@ -358,6 +361,7 @@
 
 - (void)windowDidEnterFullScreen:(NSNotification *_Nonnull)notification
 {
+    _isTransitioningToFullScreen = false;
     auto parent = dynamic_cast<IWindowStateChanged*>(_parent.operator->());
 
     if(parent != nullptr)
@@ -440,7 +444,10 @@
                     _parent->BaseEvents->RawMouseEvent(NonClientLeftButtonDown, static_cast<uint32>([event timestamp] * 1000), AvnInputModifiersNone, point, delta);
                 }
                 
-                _parent->BringToFront();
+                if(!_isTransitioningToFullScreen)
+                {
+                    _parent->BringToFront();
+                }
             }
             break;
 
diff --git a/native/Avalonia.Native/src/OSX/PopupImpl.mm b/native/Avalonia.Native/src/OSX/PopupImpl.mm
index 7ed780359d..b29b44b6cc 100644
--- a/native/Avalonia.Native/src/OSX/PopupImpl.mm
+++ b/native/Avalonia.Native/src/OSX/PopupImpl.mm
@@ -25,17 +25,13 @@ private:
     PopupImpl(IAvnWindowEvents* events, IAvnGlContext* gl) : WindowBaseImpl(events, gl)
     {
         WindowEvents = events;
+        [Window setLevel:NSPopUpMenuWindowLevel];
     }
 protected:
     virtual NSWindowStyleMask GetStyle() override
     {
         return NSWindowStyleMaskBorderless;
     }
-    
-    virtual void OnInitialiseNSWindow () override
-    {
-        [Window setLevel:NSPopUpMenuWindowLevel];
-    }
 
 public:
     virtual bool ShouldTakeFocusOnShow() override
diff --git a/native/Avalonia.Native/src/OSX/WindowBaseImpl.h b/native/Avalonia.Native/src/OSX/WindowBaseImpl.h
index 040ba39b6d..787827c9b4 100644
--- a/native/Avalonia.Native/src/OSX/WindowBaseImpl.h
+++ b/native/Avalonia.Native/src/OSX/WindowBaseImpl.h
@@ -106,8 +106,6 @@ protected:
     virtual NSWindowStyleMask GetStyle();
 
     void UpdateStyle();
-                           
-    virtual void OnInitialiseNSWindow ();
 
 private:
     void CreateNSWindow (bool isDialog);
diff --git a/native/Avalonia.Native/src/OSX/WindowBaseImpl.mm b/native/Avalonia.Native/src/OSX/WindowBaseImpl.mm
index 067383349f..289694a9b8 100644
--- a/native/Avalonia.Native/src/OSX/WindowBaseImpl.mm
+++ b/native/Avalonia.Native/src/OSX/WindowBaseImpl.mm
@@ -89,8 +89,6 @@ HRESULT WindowBaseImpl::Show(bool activate, bool isDialog) {
     START_COM_CALL;
 
     @autoreleasepool {
-        InitialiseNSWindow();
-
         if(hasPosition)
         {
             SetPosition(lastPositionSet);
@@ -568,11 +566,6 @@ void WindowBaseImpl::CreateNSWindow(bool isDialog) {
     }
 }
 
-void WindowBaseImpl::OnInitialiseNSWindow()
-{
-    
-}
-
 void WindowBaseImpl::InitialiseNSWindow() {
     if(Window != nullptr) {
         [Window setContentView:StandardContainer];
@@ -595,8 +588,6 @@ void WindowBaseImpl::InitialiseNSWindow() {
                 [GetWindowProtocol() showWindowMenuWithAppMenu];
             }
         }
-        
-        OnInitialiseNSWindow();
     }
 }
 
diff --git a/native/Avalonia.Native/src/OSX/WindowImpl.h b/native/Avalonia.Native/src/OSX/WindowImpl.h
index 76d5cbf6ea..b4b1d4e70b 100644
--- a/native/Avalonia.Native/src/OSX/WindowImpl.h
+++ b/native/Avalonia.Native/src/OSX/WindowImpl.h
@@ -13,6 +13,7 @@
 class WindowImpl : public virtual WindowBaseImpl, public virtual IAvnWindow, public IWindowStateChanged
 {
 private:
+    bool _isEnabled;
     bool _canResize;
     bool _fullScreenActive;
     SystemDecorations _decorations;
@@ -92,8 +93,6 @@ BEGIN_INTERFACE_MAP()
 
     virtual bool IsDialog() override;
     
-    virtual void OnInitialiseNSWindow() override;
-    
     virtual void BringToFront () override;
     
     bool CanBecomeKeyWindow ();
@@ -102,6 +101,7 @@ protected:
     virtual NSWindowStyleMask GetStyle() override;
 
 private:
+    void OnInitialiseNSWindow();
     NSString *_lastTitle;
 };
 
diff --git a/native/Avalonia.Native/src/OSX/WindowImpl.mm b/native/Avalonia.Native/src/OSX/WindowImpl.mm
index 9d4d0b8e21..782c8b80dc 100644
--- a/native/Avalonia.Native/src/OSX/WindowImpl.mm
+++ b/native/Avalonia.Native/src/OSX/WindowImpl.mm
@@ -9,6 +9,7 @@
 #include "WindowProtocol.h"
 
 WindowImpl::WindowImpl(IAvnWindowEvents *events, IAvnGlContext *gl) : WindowBaseImpl(events, gl) {
+    _isEnabled = true;
     _children = std::list<WindowImpl*>();
     _isClientAreaExtended = false;
     _extendClientHints = AvnDefaultChrome;
@@ -22,6 +23,8 @@ WindowImpl::WindowImpl(IAvnWindowEvents *events, IAvnGlContext *gl) : WindowBase
     _lastTitle = @"";
     _parent = nullptr;
     WindowEvents = events;
+    
+    OnInitialiseNSWindow();
 }
 
 void WindowImpl::HideOrShowTrafficLights() {
@@ -30,15 +33,16 @@ void WindowImpl::HideOrShowTrafficLights() {
     }
 
     bool wantsChrome = (_extendClientHints & AvnSystemChrome) || (_extendClientHints & AvnPreferSystemChrome);
-    bool hasTrafficLights = _isClientAreaExtended ? !wantsChrome : _decorations != SystemDecorationsFull;
+    bool hasTrafficLights = _isClientAreaExtended ? wantsChrome : _decorations == SystemDecorationsFull;
     
-    [[Window standardWindowButton:NSWindowCloseButton] setHidden:hasTrafficLights];
-    [[Window standardWindowButton:NSWindowMiniaturizeButton] setHidden:hasTrafficLights];
-    [[Window standardWindowButton:NSWindowZoomButton] setHidden:hasTrafficLights];
+    [[Window standardWindowButton:NSWindowCloseButton] setHidden:!hasTrafficLights];
+    [[Window standardWindowButton:NSWindowMiniaturizeButton] setHidden:!hasTrafficLights];
+    [[Window standardWindowButton:NSWindowZoomButton] setHidden:!hasTrafficLights];
 }
 
 void WindowImpl::OnInitialiseNSWindow(){
     [GetWindowProtocol() setCanBecomeKeyWindow:true];
+    
     [Window disableCursorRects];
     [Window setTabbingMode:NSWindowTabbingModeDisallowed];
     [Window setCollectionBehavior:NSWindowCollectionBehaviorFullScreenPrimary];
@@ -75,7 +79,9 @@ HRESULT WindowImpl::SetEnabled(bool enable) {
     START_COM_CALL;
 
     @autoreleasepool {
+        _isEnabled = enable;
         [GetWindowProtocol() setEnabled:enable];
+        UpdateStyle();
         return S_OK;
     }
 }
@@ -87,11 +93,8 @@ HRESULT WindowImpl::SetParent(IAvnWindow *parent) {
         if(_parent != nullptr)
         {
             _parent->_children.remove(this);
-            auto parent = _parent;
             
-            dispatch_async(dispatch_get_main_queue(), ^{
-                parent->BringToFront();
-            });
+            _parent->BringToFront();
         }
 
         auto cparent = dynamic_cast<WindowImpl *>(parent);
@@ -118,20 +121,23 @@ HRESULT WindowImpl::SetParent(IAvnWindow *parent) {
 
 void WindowImpl::BringToFront()
 {
-    if(IsDialog())
+    if(Window != nullptr)
     {
-        Activate();
-    }
-    else
-    {
-        [Window orderFront:nullptr];
-    }
-    
-    [Window invalidateShadow];
-    
-    for(auto iterator = _children.begin(); iterator != _children.end(); iterator++)
-    {
-        (*iterator)->BringToFront();
+        if(IsDialog())
+        {
+            Activate();
+        }
+        else
+        {
+            [Window orderFront:nullptr];
+        }
+        
+        [Window invalidateShadow];
+        
+        for(auto iterator = _children.begin(); iterator != _children.end(); iterator++)
+        {
+            (*iterator)->BringToFront();
+        }
     }
 }
 
@@ -560,6 +566,11 @@ bool WindowImpl::IsDialog() {
 
 NSWindowStyleMask WindowImpl::GetStyle() {
     unsigned long s = NSWindowStyleMaskBorderless;
+    
+    if(_actualWindowState == FullScreen)
+    {
+        s |= NSWindowStyleMaskFullScreen;
+    }
 
     switch (_decorations) {
         case SystemDecorationsNone:
@@ -573,7 +584,7 @@ NSWindowStyleMask WindowImpl::GetStyle() {
         case SystemDecorationsFull:
             s = s | NSWindowStyleMaskTitled | NSWindowStyleMaskClosable;
 
-            if (_canResize) {
+            if (_canResize && _isEnabled) {
                 s = s | NSWindowStyleMaskResizable;
             }
             break;
diff --git a/samples/ControlCatalog/MainWindow.xaml.cs b/samples/ControlCatalog/MainWindow.xaml.cs
index dd62698cc7..3bad18c815 100644
--- a/samples/ControlCatalog/MainWindow.xaml.cs
+++ b/samples/ControlCatalog/MainWindow.xaml.cs
@@ -32,8 +32,6 @@ namespace ControlCatalog
 
             DataContext = new MainWindowViewModel(_notificationArea);
             _recentMenu = ((NativeMenu.GetMenu(this).Items[0] as NativeMenuItem).Menu.Items[2] as NativeMenuItem).Menu;
-
-            ExtendClientAreaChromeHints = Avalonia.Platform.ExtendClientAreaChromeHints.OSXThickTitleBar;
         }
 
         public static string MenuQuitHeader => RuntimeInformation.IsOSPlatform(OSPlatform.OSX) ? "Quit Avalonia" : "E_xit";
diff --git a/src/Avalonia.Controls/Flyouts/FlyoutBase.cs b/src/Avalonia.Controls/Flyouts/FlyoutBase.cs
index bdabfbd6c8..0c1eed7534 100644
--- a/src/Avalonia.Controls/Flyouts/FlyoutBase.cs
+++ b/src/Avalonia.Controls/Flyouts/FlyoutBase.cs
@@ -221,7 +221,7 @@ namespace Avalonia.Controls.Primitives
                 ((ISetLogicalParent)Popup).SetParent(null);
             }
 
-            if (Popup.PlacementTarget != placementTarget)
+            if (Popup.Parent == null || Popup.PlacementTarget != placementTarget)
             {
                 Popup.PlacementTarget = Target = placementTarget;
                 ((ISetLogicalParent)Popup).SetParent(placementTarget);
diff --git a/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs b/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs
index 8b77074960..776b4508c2 100644
--- a/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs
+++ b/tests/Avalonia.Controls.UnitTests/FlyoutTests.cs
@@ -451,6 +451,28 @@ namespace Avalonia.Controls.UnitTests
                 Assert.Null(popup.Parent);
             }
         }
+        
+        [Fact]
+        public void Should_Reset_Popup_Parent_On_Target_Attach_Following_Detach()
+        {
+            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);
+                
+                flyout.Hide();
+                
+                flyout.ShowAt(userControl);
+                Assert.NotNull(popup.Parent);
+            }
+        }
 
         [Fact]
         public void ContextFlyout_Can_Be_Set_In_Styles()