diff --git a/doc/ReleaseNotes/_ReleaseNotes.md b/doc/ReleaseNotes/_ReleaseNotes.md
index 9a76348aa6a8..a1390d339243 100644
--- a/doc/ReleaseNotes/_ReleaseNotes.md
+++ b/doc/ReleaseNotes/_ReleaseNotes.md
@@ -85,8 +85,8 @@
 * `Grid` now supports `ColumnDefinition.MinWidth` and `MaxWidth` and `RowDefinition.MinHeight` and `MaxHeight` (#1032)
 * Implement the `PivotPanel` measure/arrange to allow text wrapping in pivot items
 * [Wasm] Add `PathIcon` support
+* [iOS] Fix items dependency property propagation in ListView items
 * [Wasm] Add UI Testing support through for `Uno.UI.Helpers.Automation.GetDependencyPropertyValue`\
-* Add automated UI testing support for every PR
 
 ### Breaking Changes
 * The `WebAssemblyRuntime.InvokeJSUnmarshalled` method with three parameters has been removed.
diff --git a/src/SamplesApp/UITests.Shared/UITests.Shared.projitems b/src/SamplesApp/UITests.Shared/UITests.Shared.projitems
index 86159d7da38e..95162145f7c1 100644
--- a/src/SamplesApp/UITests.Shared/UITests.Shared.projitems
+++ b/src/SamplesApp/UITests.Shared/UITests.Shared.projitems
@@ -1,4 +1,4 @@
-<?xml version="1.0" encoding="utf-8"?>
+<?xml version="1.0" encoding="utf-8"?>
 <Project xmlns="http://schemas.microsoft.com/developer/msbuild/2003">
   <PropertyGroup>
     <MSBuildAllProjects>$(MSBuildAllProjects);$(MSBuildThisFileFullPath)</MSBuildAllProjects>
@@ -833,6 +833,10 @@
       <SubType>Designer</SubType>
       <Generator>MSBuild:Compile</Generator>
     </Page>
+    <Page Include="$(MSBuildThisFileDirectory)Windows_UI_Xaml_Controls\ListView\ListView_DataContext_Propagation.xaml">
+      <SubType>Designer</SubType>
+      <Generator>MSBuild:Compile</Generator>
+    </Page>
     <Page Include="$(MSBuildThisFileDirectory)Windows_UI_Xaml_Controls\ListView\ListView_Infinite_Breadth.xaml">
       <SubType>Designer</SubType>
       <Generator>MSBuild:Compile</Generator>
@@ -2437,6 +2441,7 @@
     <Compile Include="$(MSBuildThisFileDirectory)Windows_UI_Xaml_Controls\ListView\ListViewResizableText.xaml.cs">
       <DependentUpon>ListViewResizableText.xaml</DependentUpon>
     </Compile>
+    <Compile Include="$(MSBuildThisFileDirectory)Windows_UI_Xaml_Controls\ListView\ListView_DataContext_Propagation.xaml.cs" />
     <Compile Include="$(MSBuildThisFileDirectory)Windows_UI_Xaml_Controls\ListView\ListView_Infinite_Breadth.xaml.cs">
       <DependentUpon>ListView_Infinite_Breadth.xaml</DependentUpon>
     </Compile>
@@ -3515,8 +3520,8 @@
     <Compile Update="$(MSBuildThisFileDirectory)Windows_UI_Xaml_Controls\NavigationViewTests\NavigationView_TopNavigation.xaml.cs">
       <DependentUpon>NavigationView_TopNavigation.xaml</DependentUpon>
     </Compile>
-    <Compile Update="$(MSBuildThisFileDirectory)Windows_UI_Xaml_Controls\Pivot\PivotSimpleTest.xaml.cs">
-      <DependentUpon>PivotSimpleTest.xaml</DependentUpon>
+    <Compile Update="$(MSBuildThisFileDirectory)Windows_UI_Xaml_Controls\ListView\ListView_DataContext_Propagation.xaml.cs">
+      <DependentUpon>ListView_DataContext_Propagation.xaml</DependentUpon>
     </Compile>
     <Compile Update="$(MSBuildThisFileDirectory)Windows_UI_Xaml_Controls\Popup\MessageDialog.xaml.cs">
       <DependentUpon>MessageDialog.xaml</DependentUpon>
@@ -3720,4 +3725,4 @@
   <ItemGroup>
     <Folder Include="$(MSBuildThisFileDirectory)Windows_UI_Xaml_Controls\ChatBox\" />
   </ItemGroup>
-</Project>
+</Project>
\ No newline at end of file
diff --git a/src/SamplesApp/UITests.Shared/Windows_UI_Xaml_Controls/ListView/ListView_DataContext_Propagation.xaml b/src/SamplesApp/UITests.Shared/Windows_UI_Xaml_Controls/ListView/ListView_DataContext_Propagation.xaml
new file mode 100644
index 000000000000..6870dba63136
--- /dev/null
+++ b/src/SamplesApp/UITests.Shared/Windows_UI_Xaml_Controls/ListView/ListView_DataContext_Propagation.xaml
@@ -0,0 +1,48 @@
+<UserControl
+    x:Class="UITests.Shared.Windows_UI_Xaml_Controls.ListView.ListView_DataContext_Propagation"
+    xmlns="http://schemas.microsoft.com/winfx/2006/xaml/presentation"
+    xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
+    xmlns:local="using:UITests.Shared.Windows_UI_Xaml_Controls.ListView"
+    xmlns:d="http://schemas.microsoft.com/expression/blend/2008"
+    xmlns:mc="http://schemas.openxmlformats.org/markup-compatibility/2006"
+    mc:Ignorable="d"
+    d:DesignHeight="300"
+    d:DesignWidth="400">
+    
+    <Grid x:Name="topGrid" DataContext="This is the datacontext">
+        <TextBlock x:Name="Title" Text="{Binding}"/>
+
+        <ListView
+                    Margin="0,20,0,0" 
+                    HorizontalContentAlignment="Stretch"
+                    SelectionMode="None"
+                    IsItemClickEnabled="False">
+            <ListView.ItemContainerStyle>
+                <Style TargetType="ListViewItem">
+                    <Setter Property="HorizontalContentAlignment" Value="Stretch" />
+                    <Setter Property="Padding" Value="0" />
+                    <Setter Property="Margin" Value="0" />
+                </Style>
+            </ListView.ItemContainerStyle>
+            <ListView.ItemTemplate>
+                <DataTemplate>
+                    <RelativePanel Margin="0,20,0,0">
+                        <Button FontSize="12" Click="Button_Click">
+                            <Button.Content>
+                                <TextBlock>
+									<Run Text="Should be 'this is the DataContext': " />
+									<Run Text="{Binding Text,ElementName=Title}" />
+                                </TextBlock>
+                            </Button.Content>
+                        </Button>
+                    </RelativePanel>
+
+                </DataTemplate>
+            </ListView.ItemTemplate>
+
+            <x:String>Item 01</x:String>
+            <x:String>Item 02</x:String>
+        </ListView>
+
+    </Grid>
+</UserControl>
diff --git a/src/SamplesApp/UITests.Shared/Windows_UI_Xaml_Controls/ListView/ListView_DataContext_Propagation.xaml.cs b/src/SamplesApp/UITests.Shared/Windows_UI_Xaml_Controls/ListView/ListView_DataContext_Propagation.xaml.cs
new file mode 100644
index 000000000000..cb331d9872ed
--- /dev/null
+++ b/src/SamplesApp/UITests.Shared/Windows_UI_Xaml_Controls/ListView/ListView_DataContext_Propagation.xaml.cs
@@ -0,0 +1,34 @@
+using System;
+using System.Collections.Generic;
+using System.IO;
+using System.Linq;
+using System.Runtime.InteropServices.WindowsRuntime;
+using Uno.UI.Samples.Controls;
+using Windows.Foundation;
+using Windows.Foundation.Collections;
+using Windows.UI.Xaml;
+using Windows.UI.Xaml.Controls;
+using Windows.UI.Xaml.Controls.Primitives;
+using Windows.UI.Xaml.Data;
+using Windows.UI.Xaml.Input;
+using Windows.UI.Xaml.Media;
+using Windows.UI.Xaml.Navigation;
+
+// The User Control item template is documented at https://go.microsoft.com/fwlink/?LinkId=234236
+
+namespace UITests.Shared.Windows_UI_Xaml_Controls.ListView
+{
+    [SampleControlInfo("ListView", "ListView_DataContext_Propagation")]
+    public sealed partial class ListView_DataContext_Propagation : UserControl
+    {
+        public ListView_DataContext_Propagation()
+        {
+            this.InitializeComponent();
+        }
+
+        private void Button_Click(object sender, RoutedEventArgs e)
+        {
+            topGrid.DataContext = "Button Clicked " + sender.ToString();
+        }
+    }
+}
diff --git a/src/Uno.UI/Controls/BindableImageView.Android.cs b/src/Uno.UI/Controls/BindableImageView.Android.cs
index b780011fb24d..928238d7f3a0 100644
--- a/src/Uno.UI/Controls/BindableImageView.Android.cs
+++ b/src/Uno.UI/Controls/BindableImageView.Android.cs
@@ -24,7 +24,6 @@
 using Java.Lang.Ref;
 using System.IO;
 using Math = System.Math;
-using System.Drawing;
 using Size = System.Drawing.Size;
 using System.Reflection;
 using Windows.UI.Core;
diff --git a/src/Uno.UI/UI/Xaml/Controls/BorderLayerRenderer.Android.cs b/src/Uno.UI/UI/Xaml/Controls/BorderLayerRenderer.Android.cs
index 0eaf19abe43f..3a07b0e2edc4 100644
--- a/src/Uno.UI/UI/Xaml/Controls/BorderLayerRenderer.Android.cs
+++ b/src/Uno.UI/UI/Xaml/Controls/BorderLayerRenderer.Android.cs
@@ -10,7 +10,6 @@
 using Windows.UI.Xaml.Media;
 using System;
 using System.Collections.Generic;
-using System.Drawing;
 using Uno.Disposables;
 using System.Text;
 using System.Threading;
@@ -51,7 +50,7 @@ public void UpdateLayers(
 			// This is required because android Height and Width are hidden by Control.
 			var baseView = view as View;
 
-			Size targetSize = new Size(baseView.Width, baseView.Height);
+			var targetSize = new global::System.Drawing.Size(baseView.Width, baseView.Height);
 			var drawArea = new Windows.Foundation.Rect(0, 0, targetSize.Width, targetSize.Height);
 			var newState = new LayoutState(drawArea, background, borderThickness, borderBrush, cornerRadius, padding);
 			var previousLayoutState = _currentState;
@@ -239,7 +238,7 @@ Action onImageSet
 					{
 						using (var strokePaint = new Paint(borderBrush.GetStrokePaint(drawArea)))
 						{
-							var overlay = GetOverlayDrawable(strokePaint, physicalBorderThickness, new Size((int)drawArea.Width, (int)drawArea.Height), path);
+							var overlay = GetOverlayDrawable(strokePaint, physicalBorderThickness, new global::System.Drawing.Size((int)drawArea.Width, (int)drawArea.Height), path);
 
 							if (overlay != null)
 							{
@@ -274,7 +273,7 @@ Action onImageSet
 					//TODO: Handle case that BorderBrush is an ImageBrush
 					using (var strokePaint = borderBrush.GetStrokePaint(drawArea))
 					{
-						var overlay = GetOverlayDrawable(strokePaint, physicalBorderThickness, new Size(view.Width, view.Height));
+						var overlay = GetOverlayDrawable(strokePaint, physicalBorderThickness, new global::System.Drawing.Size(view.Width, view.Height));
 
 						if (overlay != null)
 						{
@@ -423,7 +422,7 @@ private static void ExecuteWithNoRelayout(BindableView target, Action<BindableVi
 			}
 		}
 
-		private static Drawable GetOverlayDrawable(Paint strokePaint, Thickness physicalBorderThickness, Size viewSize, Path path = null)
+		private static Drawable GetOverlayDrawable(Paint strokePaint, Thickness physicalBorderThickness, global::System.Drawing.Size viewSize, Path path = null)
 		{
 			if (strokePaint != null)
 			{
diff --git a/src/Uno.UI/UI/Xaml/Controls/ListViewBase/ListViewBaseSource.iOS.cs b/src/Uno.UI/UI/Xaml/Controls/ListViewBase/ListViewBaseSource.iOS.cs
index 7f680014d356..da432cb7ee2d 100644
--- a/src/Uno.UI/UI/Xaml/Controls/ListViewBase/ListViewBaseSource.iOS.cs
+++ b/src/Uno.UI/UI/Xaml/Controls/ListViewBase/ListViewBaseSource.iOS.cs
@@ -229,7 +229,11 @@ public override UICollectionViewCell GetCell(UICollectionView collectionView, NS
 						}
 
 						FrameworkElement.InitializePhaseBinding(selectorItem);
-					}
+                        
+                        // Ensure the item has a parent, since it's added to the native collection view
+                        // which does not automatically sets the parent DependencyObject.
+                        selectorItem.SetParent(Owner?.XamlParent);
+                    }
 					else if (this.Log().IsEnabled(Microsoft.Extensions.Logging.LogLevel.Debug))
 					{
 						this.Log().Debug($"Reusing view at indexPath={indexPath}, previously bound to {selectorItem.DataContext}.");
diff --git a/src/Uno.UI/UI/Xaml/Controls/Panel/Panel.Android.cs b/src/Uno.UI/UI/Xaml/Controls/Panel/Panel.Android.cs
index ecc8eca58223..de7c0f03e09e 100644
--- a/src/Uno.UI/UI/Xaml/Controls/Panel/Panel.Android.cs
+++ b/src/Uno.UI/UI/Xaml/Controls/Panel/Panel.Android.cs
@@ -13,7 +13,6 @@
 using System.Runtime.CompilerServices;
 using Android.Graphics;
 using Android.Graphics.Drawables;
-using System.Drawing;
 using Uno.UI;
 using Windows.UI.Xaml.Media;
 
diff --git a/src/Uno.UI/UI/Xaml/Media/ImageSource.Android.cs b/src/Uno.UI/UI/Xaml/Media/ImageSource.Android.cs
index f75ae97a634e..4ccb5b09e873 100644
--- a/src/Uno.UI/UI/Xaml/Media/ImageSource.Android.cs
+++ b/src/Uno.UI/UI/Xaml/Media/ImageSource.Android.cs
@@ -6,7 +6,6 @@
 using System;
 using System.Collections.Generic;
 using System.ComponentModel;
-using System.Drawing;
 using System.Globalization;
 using System.IO;
 using System.Linq;
@@ -26,7 +25,7 @@ public partial class ImageSource
 		private const string ContactUriPrefix = "content://com.android.contacts/";
 
 		private static bool _resourceCacheLock;
-		private static Dictionary<Tuple<int, Size?>, Bitmap> _resourceCache = new Dictionary<Tuple<int, Size?>, Bitmap>();
+		private static Dictionary<Tuple<int, global::System.Drawing.Size?>, Bitmap> _resourceCache = new Dictionary<Tuple<int, global::System.Drawing.Size?>, Bitmap>();
 
 		/// <summary>
 		/// Defines an asynchronous image loader handler.
@@ -35,7 +34,7 @@ public partial class ImageSource
 		/// <param name="uri">The image uri</param>
 		/// <param name="targetSize">An optional target decoding size</param>
 		/// <returns>A Bitmap instance</returns>
-		public delegate Task<Bitmap> ImageLoaderHandler(CancellationToken ct, string uri, Android.Widget.ImageView imageView, Size? targetSize);
+		public delegate Task<Bitmap> ImageLoaderHandler(CancellationToken ct, string uri, Android.Widget.ImageView imageView, global::System.Drawing.Size? targetSize);
 
 		/// <summary>
 		/// Provides a optional external image loader.
@@ -131,7 +130,7 @@ internal async Task<Bitmap> Open(CancellationToken ct, Android.Widget.ImageView
 			options.InJustDecodeBounds = true;
 
 			var targetSize = UseTargetSize && targetWidth != null && targetHeight != null
-				? (Size?)new Size(targetWidth.Value, targetHeight.Value)
+				? (global::System.Drawing.Size?)new global::System.Drawing.Size(targetWidth.Value, targetHeight.Value)
 				: null;
 
 			if (ResourceId.HasValue)
@@ -273,7 +272,7 @@ private static bool IsContactUri(Uri uri)
 		/// <param name="resourceId"></param>
 		/// <param name="targetSize"></param>
 		/// <returns></returns>
-		private async Task<Bitmap> FetchResourceWithDownsampling(CancellationToken ct, int resourceId, Size? targetSize)
+		private async Task<Bitmap> FetchResourceWithDownsampling(CancellationToken ct, int resourceId, global::System.Drawing.Size? targetSize)
 		{
 			var key = Tuple.Create(resourceId, targetSize);