diff --git a/native/Avalonia.Native/src/OSX/AvnView.mm b/native/Avalonia.Native/src/OSX/AvnView.mm
index 4ae6ad5a00..bcfdc23053 100644
--- a/native/Avalonia.Native/src/OSX/AvnView.mm
+++ b/native/Avalonia.Native/src/OSX/AvnView.mm
@@ -127,11 +127,8 @@
         [self updateRenderTarget];
 
         auto reason = [self inLiveResize] ? ResizeUser : _resizeReason;
-        
-        if(_parent->IsShown())
-        {
-            _parent->BaseEvents->Resized(AvnSize{newSize.width, newSize.height}, reason);
-        }
+
+        _parent->BaseEvents->Resized(AvnSize{newSize.width, newSize.height}, reason);
     }
 }
 
diff --git a/native/Avalonia.Native/src/OSX/WindowBaseImpl.mm b/native/Avalonia.Native/src/OSX/WindowBaseImpl.mm
index 59102e15a6..b579920c6b 100644
--- a/native/Avalonia.Native/src/OSX/WindowBaseImpl.mm
+++ b/native/Avalonia.Native/src/OSX/WindowBaseImpl.mm
@@ -4,6 +4,7 @@
 //
 
 #import <AppKit/AppKit.h>
+#import <Cocoa/Cocoa.h>
 #include "common.h"
 #include "AvnView.h"
 #include "menu.h"
@@ -293,15 +294,24 @@ HRESULT WindowBaseImpl::Resize(double x, double y, AvnPlatformResizeReason reaso
         }
 
         @try {
-            if(x != lastSize.width || y != lastSize.height) {
-                lastSize = NSSize{x, y};
-
+            if(x != lastSize.width || y != lastSize.height)
+            {
                 if (!_shown) {
-                    BaseEvents->Resized(AvnSize{x, y}, reason);
-                } else if (Window != nullptr) {
-                    [Window setContentSize:lastSize];
-                    [Window invalidateShadow];
+                    auto screenSize = [Window screen].visibleFrame.size;
+
+                    if (x > screenSize.width) {
+                        x = screenSize.width;
+                    }
+
+                    if (y > screenSize.height) {
+                        y = screenSize.height;
+                    }
                 }
+
+                lastSize = NSSize{x, y};
+
+                [Window setContentSize:lastSize];
+                [Window invalidateShadow];
             }
         }
         @finally {
diff --git a/native/Avalonia.Native/src/OSX/WindowImpl.mm b/native/Avalonia.Native/src/OSX/WindowImpl.mm
index cf1ee6943d..840f2c9e88 100644
--- a/native/Avalonia.Native/src/OSX/WindowImpl.mm
+++ b/native/Avalonia.Native/src/OSX/WindowImpl.mm
@@ -54,6 +54,11 @@ HRESULT WindowImpl::Show(bool activate, bool isDialog) {
 
         WindowBaseImpl::Show(activate, isDialog);
         GetWindowState(&_actualWindowState);
+
+        if(IsZoomed()) {
+            _lastWindowState = _actualWindowState;
+        }
+
         return SetWindowState(_lastWindowState);
     }
 }
diff --git a/samples/IntegrationTestApp/ShowWindowTest.axaml b/samples/IntegrationTestApp/ShowWindowTest.axaml
index 5162eeee92..bd6910dd4d 100644
--- a/samples/IntegrationTestApp/ShowWindowTest.axaml
+++ b/samples/IntegrationTestApp/ShowWindowTest.axaml
@@ -1,41 +1,48 @@
 <Window xmlns="https://github.com/avaloniaui"
         xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
+        xmlns:integrationTestApp="clr-namespace:IntegrationTestApp"
         x:Class="IntegrationTestApp.ShowWindowTest"
         Name="SecondaryWindow"
         x:DataType="Window"
         Title="Show Window Test">
-  <Grid ColumnDefinitions="Auto,Auto" RowDefinitions="Auto,Auto,Auto,Auto,Auto,Auto,Auto,Auto,Auto,Auto">
-    <Label Grid.Column="0" Grid.Row="1">Client Size</Label>
-    <TextBox Name="CurrentClientSize" Grid.Column="1" Grid.Row="1" IsReadOnly="True"
-             Text="{Binding ClientSize, Mode=OneWay}"/>
-    
-    <Label Grid.Column="0" Grid.Row="2">Frame Size</Label>
-    <TextBox Name="CurrentFrameSize" Grid.Column="1" Grid.Row="2" IsReadOnly="True"
-             Text="{Binding FrameSize, Mode=OneWay}"/>
-
-    <Label Grid.Column="0" Grid.Row="3">Position</Label>
-    <TextBox Name="CurrentPosition" Grid.Column="1" Grid.Row="3" IsReadOnly="True"/>
-
-    <Label Grid.Column="0" Grid.Row="4">Owner Rect</Label>
-    <TextBox Name="CurrentOwnerRect" Grid.Column="1" Grid.Row="4" IsReadOnly="True"/>
-    
-    <Label Grid.Column="0" Grid.Row="5">Screen Rect</Label>
-    <TextBox Name="CurrentScreenRect" Grid.Column="1" Grid.Row="5" IsReadOnly="True"/>
-
-    <Label Grid.Column="0" Grid.Row="6">Scaling</Label>
-    <TextBox Name="CurrentScaling" Grid.Column="1" Grid.Row="6" IsReadOnly="True"/>
-    
-    <Label Grid.Column="0" Grid.Row="7">WindowState</Label>
-    <ComboBox Name="CurrentWindowState" Grid.Column="1" Grid.Row="7" SelectedIndex="{Binding WindowState}">
-      <ComboBoxItem Name="WindowStateNormal">Normal</ComboBoxItem>
-      <ComboBoxItem Name="WindowStateMinimized">Minimized</ComboBoxItem>
-      <ComboBoxItem Name="WindowStateMaximized">Maximized</ComboBoxItem>
-      <ComboBoxItem Name="WindowStateFullScreen">FullScreen</ComboBoxItem>
-    </ComboBox>
-
-    <Label Grid.Column="0" Grid.Row="8">Order (mac)</Label>
-    <TextBox Name="CurrentOrder" Grid.Column="1" Grid.Row="8" IsReadOnly="True"/>
-
-    <Button Name="HideButton" Grid.Row="9" Command="{Binding $parent[Window].Hide}">Hide</Button>
-  </Grid>
+  <integrationTestApp:MeasureBorder Name="MyBorder">
+    <Grid ColumnDefinitions="Auto,Auto" RowDefinitions="Auto,Auto,Auto,Auto,Auto,Auto,Auto,Auto,Auto,Auto,Auto">
+      <Label Grid.Column="0" Grid.Row="1">Client Size</Label>
+      <TextBox Name="CurrentClientSize" Grid.Column="1" Grid.Row="1" IsReadOnly="True"
+               Text="{Binding ClientSize, Mode=OneWay}" />
+
+      <Label Grid.Column="0" Grid.Row="2">Frame Size</Label>
+      <TextBox Name="CurrentFrameSize" Grid.Column="1" Grid.Row="2" IsReadOnly="True"
+               Text="{Binding FrameSize, Mode=OneWay}" />
+
+      <Label Grid.Column="0" Grid.Row="3">Position</Label>
+      <TextBox Name="CurrentPosition" Grid.Column="1" Grid.Row="3" IsReadOnly="True" />
+
+      <Label Grid.Column="0" Grid.Row="4">Owner Rect</Label>
+      <TextBox Name="CurrentOwnerRect" Grid.Column="1" Grid.Row="4" IsReadOnly="True" />
+
+      <Label Grid.Column="0" Grid.Row="5">Screen Rect</Label>
+      <TextBox Name="CurrentScreenRect" Grid.Column="1" Grid.Row="5" IsReadOnly="True" />
+
+      <Label Grid.Column="0" Grid.Row="6">Scaling</Label>
+      <TextBox Name="CurrentScaling" Grid.Column="1" Grid.Row="6" IsReadOnly="True" />
+
+      <Label Grid.Column="0" Grid.Row="7">WindowState</Label>
+      <ComboBox Name="CurrentWindowState" Grid.Column="1" Grid.Row="7" SelectedIndex="{Binding WindowState}">
+        <ComboBoxItem Name="WindowStateNormal">Normal</ComboBoxItem>
+        <ComboBoxItem Name="WindowStateMinimized">Minimized</ComboBoxItem>
+        <ComboBoxItem Name="WindowStateMaximized">Maximized</ComboBoxItem>
+        <ComboBoxItem Name="WindowStateFullScreen">FullScreen</ComboBoxItem>
+      </ComboBox>
+
+      <Label Grid.Column="0" Grid.Row="8">Order (mac)</Label>
+      <TextBox Name="CurrentOrder" Grid.Column="1" Grid.Row="8" IsReadOnly="True" />
+      
+      <Label Grid.Row="9" Content="MeasuredWith:" />
+      <TextBlock Grid.Column="1" Grid.Row="9" Name="CurrentMeasuredWithText" Text="{Binding #MyBorder.MeasuredWith}" />
+
+      <Button Name="HideButton" Grid.Row="10" Command="{Binding $parent[Window].Hide}">Hide</Button>
+      
+    </Grid>
+  </integrationTestApp:MeasureBorder>
 </Window>
diff --git a/samples/IntegrationTestApp/ShowWindowTest.axaml.cs b/samples/IntegrationTestApp/ShowWindowTest.axaml.cs
index 1a267ea20b..f0be34fdaa 100644
--- a/samples/IntegrationTestApp/ShowWindowTest.axaml.cs
+++ b/samples/IntegrationTestApp/ShowWindowTest.axaml.cs
@@ -7,6 +7,25 @@ using Avalonia.Threading;
 
 namespace IntegrationTestApp
 {
+    public class MeasureBorder : Border
+    {
+        protected override Size MeasureOverride(Size availableSize)
+        {
+            MeasuredWith = availableSize;
+            
+            return base.MeasureOverride(availableSize);
+        }
+
+        public static readonly StyledProperty<Size> MeasuredWithProperty = AvaloniaProperty.Register<MeasureBorder, Size>(
+            nameof(MeasuredWith));
+
+        public Size MeasuredWith
+        {
+            get => GetValue(MeasuredWithProperty);
+            set => SetValue(MeasuredWithProperty, value);
+        }
+    }
+    
     public class ShowWindowTest : Window
     {
         private readonly DispatcherTimer? _timer;
diff --git a/tests/Avalonia.IntegrationTests.Appium/WindowTests.cs b/tests/Avalonia.IntegrationTests.Appium/WindowTests.cs
index 79eea09e01..6921a23161 100644
--- a/tests/Avalonia.IntegrationTests.Appium/WindowTests.cs
+++ b/tests/Avalonia.IntegrationTests.Appium/WindowTests.cs
@@ -4,6 +4,7 @@ using System.Linq;
 using System.Runtime.InteropServices;
 using System.Threading;
 using Avalonia.Controls;
+using Avalonia.Utilities;
 using Avalonia.Media.Imaging;
 using OpenQA.Selenium;
 using OpenQA.Selenium.Appium;
@@ -143,6 +144,24 @@ namespace Avalonia.IntegrationTests.Appium
 
             }
         }
+        
+        [Fact]
+        public void Showing_Window_With_Size_Larger_Than_Screen_Measures_Content_With_Working_Area()
+        {
+            using (OpenWindow(new Size(4000, 2200), ShowWindowMode.NonOwned, WindowStartupLocation.Manual))
+            {
+                var screenRectTextBox = _session.FindElementByAccessibilityId("CurrentClientSize");
+                var measuredWithTextBlock = _session.FindElementByAccessibilityId("CurrentMeasuredWithText");
+                
+                var measuredWithString = measuredWithTextBlock.Text;
+                var workingAreaString = screenRectTextBox.Text;
+
+                var workingArea = Size.Parse(workingAreaString);
+                var measuredWith = Size.Parse(measuredWithString);
+
+                Assert.Equal(workingArea, measuredWith);
+            }
+        }
 
         [Theory]
         [InlineData(ShowWindowMode.NonOwned)]