diff --git a/src/Controls/tests/TestCases.Android.Tests/snapshots/android/ShadowShouldUpdateOnCornerRadiusChange.png b/src/Controls/tests/TestCases.Android.Tests/snapshots/android/ShadowShouldUpdateOnCornerRadiusChange.png
new file mode 100644
index 000000000000..0ee32b56e500
Binary files /dev/null and b/src/Controls/tests/TestCases.Android.Tests/snapshots/android/ShadowShouldUpdateOnCornerRadiusChange.png differ
diff --git a/src/Controls/tests/TestCases.HostApp/Issues/Issue20596.cs b/src/Controls/tests/TestCases.HostApp/Issues/Issue20596.cs
new file mode 100644
index 000000000000..493c1977c192
--- /dev/null
+++ b/src/Controls/tests/TestCases.HostApp/Issues/Issue20596.cs
@@ -0,0 +1,49 @@
+namespace Maui.Controls.Sample.Issues;
+
+[Issue(IssueTracker.Github, 20596, "[Android] Button with corner radius shadow broken on Android device", PlatformAffected.Android | PlatformAffected.UWP)]
+public class Issue20596 : ContentPage
+{
+	public Issue20596()
+	{
+		var button = new Button
+		{
+			TextColor = Colors.Black,
+			HeightRequest = 200,
+			WidthRequest = 200,
+			BackgroundColor = Colors.Green,
+			CornerRadius = 20,
+			Shadow = new Shadow { Radius = 10 }
+		};
+
+		var imageButton = new ImageButton
+		{
+			HeightRequest = 200,
+			WidthRequest = 200,
+			BackgroundColor = Colors.Red,
+			CornerRadius = 20,
+			Shadow = new Shadow { Radius = 10 }
+		};
+
+		var updateButton = new Button
+		{
+			Text = "Update corner radius",
+			HeightRequest = 50,
+			AutomationId = "UpdateCornerRadiusButton"
+		};
+		updateButton.Clicked += (sender, e) =>
+		{
+			button.CornerRadius = 100;
+			imageButton.CornerRadius = 100;
+		};
+
+		Content = new VerticalStackLayout
+		{
+			Children =
+				{
+					button,
+					imageButton,
+					updateButton
+				}
+		};
+	}
+}
diff --git a/src/Controls/tests/TestCases.Mac.Tests/snapshots/mac/ShadowShouldUpdateOnCornerRadiusChange.png b/src/Controls/tests/TestCases.Mac.Tests/snapshots/mac/ShadowShouldUpdateOnCornerRadiusChange.png
new file mode 100644
index 000000000000..29d8cc67a611
Binary files /dev/null and b/src/Controls/tests/TestCases.Mac.Tests/snapshots/mac/ShadowShouldUpdateOnCornerRadiusChange.png differ
diff --git a/src/Controls/tests/TestCases.Shared.Tests/Tests/Issues/Issue20596.cs b/src/Controls/tests/TestCases.Shared.Tests/Tests/Issues/Issue20596.cs
new file mode 100644
index 000000000000..db5e319ffcb5
--- /dev/null
+++ b/src/Controls/tests/TestCases.Shared.Tests/Tests/Issues/Issue20596.cs
@@ -0,0 +1,23 @@
+using NUnit.Framework;
+using UITest.Appium;
+using UITest.Core;
+
+namespace Microsoft.Maui.TestCases.Tests.Issues;
+
+public class Issue20596 : _IssuesUITest
+{
+	public Issue20596(TestDevice testDevice) : base(testDevice)
+	{
+	}
+
+	public override string Issue => "[Android] Button with corner radius shadow broken on Android device";
+
+	[Test]
+	[Category(UITestCategories.Button)]
+	public void ShadowShouldUpdateOnCornerRadiusChange()
+	{
+		App.WaitForElement("UpdateCornerRadiusButton");
+		App.Click("UpdateCornerRadiusButton");
+		VerifyScreenshot();
+	}
+}
diff --git a/src/Controls/tests/TestCases.WinUI.Tests/snapshots/windows/ShadowShouldUpdateOnCornerRadiusChange.png b/src/Controls/tests/TestCases.WinUI.Tests/snapshots/windows/ShadowShouldUpdateOnCornerRadiusChange.png
new file mode 100644
index 000000000000..c5cc39af725a
Binary files /dev/null and b/src/Controls/tests/TestCases.WinUI.Tests/snapshots/windows/ShadowShouldUpdateOnCornerRadiusChange.png differ
diff --git a/src/Controls/tests/TestCases.iOS.Tests/snapshots/ios-26/ShadowShouldUpdateOnCornerRadiusChange.png b/src/Controls/tests/TestCases.iOS.Tests/snapshots/ios-26/ShadowShouldUpdateOnCornerRadiusChange.png
new file mode 100644
index 000000000000..16b48c06eb18
Binary files /dev/null and b/src/Controls/tests/TestCases.iOS.Tests/snapshots/ios-26/ShadowShouldUpdateOnCornerRadiusChange.png differ
diff --git a/src/Controls/tests/TestCases.iOS.Tests/snapshots/ios/ShadowShouldUpdateOnCornerRadiusChange.png b/src/Controls/tests/TestCases.iOS.Tests/snapshots/ios/ShadowShouldUpdateOnCornerRadiusChange.png
new file mode 100644
index 000000000000..c43ec701a9d1
Binary files /dev/null and b/src/Controls/tests/TestCases.iOS.Tests/snapshots/ios/ShadowShouldUpdateOnCornerRadiusChange.png differ
diff --git a/src/Core/src/Handlers/Button/ButtonHandler.Android.cs b/src/Core/src/Handlers/Button/ButtonHandler.Android.cs
index bd69e420f11f..32d77810e857 100644
--- a/src/Core/src/Handlers/Button/ButtonHandler.Android.cs
+++ b/src/Core/src/Handlers/Button/ButtonHandler.Android.cs
@@ -85,6 +85,11 @@ public static void MapStrokeThickness(IButtonHandler handler, IButton button)
 		public static void MapCornerRadius(IButtonHandler handler, IButton button)
 		{
 			handler.PlatformView?.UpdateCornerRadius(button);
+			
+			if (button.Shadow is not null)
+			{
+				handler.UpdateValue(nameof(IButton.Shadow));
+			}
 		}
 
 		public static void MapText(IButtonHandler handler, IText button)
diff --git a/src/Core/src/Handlers/Button/ButtonHandler.Windows.cs b/src/Core/src/Handlers/Button/ButtonHandler.Windows.cs
index d5141a1b4edd..c0fb0f0d0fb3 100644
--- a/src/Core/src/Handlers/Button/ButtonHandler.Windows.cs
+++ b/src/Core/src/Handlers/Button/ButtonHandler.Windows.cs
@@ -59,6 +59,11 @@ public static void MapStrokeThickness(IButtonHandler handler, IButtonStroke butt
 		public static void MapCornerRadius(IButtonHandler handler, IButtonStroke buttonStroke)
 		{
 			handler.PlatformView?.UpdateCornerRadius(buttonStroke);
+			
+			if (handler.VirtualView.Shadow is not null)
+			{
+				handler.UpdateValue(nameof(IButton.Shadow));
+			}
 		}
 
 		public static void MapText(IButtonHandler handler, IText button)
diff --git a/src/Core/src/Handlers/ImageButton/ImageButtonHandler.Android.cs b/src/Core/src/Handlers/ImageButton/ImageButtonHandler.Android.cs
index b71e98aa8706..f127fa519806 100644
--- a/src/Core/src/Handlers/ImageButton/ImageButtonHandler.Android.cs
+++ b/src/Core/src/Handlers/ImageButton/ImageButtonHandler.Android.cs
@@ -62,6 +62,11 @@ public static void MapCornerRadius(IImageButtonHandler handler, IButtonStroke bu
 		{
 			handler.PlatformView?.UpdateCornerRadius(buttonStroke);
 			handler.UpdateValue(nameof(IImageButton.Padding));
+
+			if (handler.VirtualView.Shadow is not null)
+			{
+				handler.UpdateValue(nameof(IImageButton.Shadow));
+			}
 		}
 
 		public static void MapPadding(IImageButtonHandler handler, IImageButton imageButton)
diff --git a/src/Core/src/Handlers/ImageButton/ImageButtonHandler.Windows.cs b/src/Core/src/Handlers/ImageButton/ImageButtonHandler.Windows.cs
index 4db50de8ea3e..6148f4785ebb 100644
--- a/src/Core/src/Handlers/ImageButton/ImageButtonHandler.Windows.cs
+++ b/src/Core/src/Handlers/ImageButton/ImageButtonHandler.Windows.cs
@@ -88,6 +88,11 @@ public static void MapCornerRadius(IImageButtonHandler handler, IButtonStroke bu
 		{
 			(handler.PlatformView as Button)?.UpdateCornerRadius(buttonStroke);
 			handler.UpdateValue(nameof(IImageButton.Padding));
+
+			if (handler.VirtualView.Shadow is not null)
+			{
+				handler.UpdateValue(nameof(IImageButton.Shadow));
+			}
 		}
 
 		public static void MapBackground(IImageButtonHandler handler, IImageButton imageButton)