diff --git a/src/Controls/src/Core/InputView/InputView.cs b/src/Controls/src/Core/InputView/InputView.cs
index c0d9863bd6d1..51cd1ff9c711 100644
--- a/src/Controls/src/Core/InputView/InputView.cs
+++ b/src/Controls/src/Core/InputView/InputView.cs
@@ -315,6 +315,29 @@ string ITextInput.Text
 			set => SetValue(TextProperty, value, SetterSpecificity.FromHandler);
 		}
 
+		private protected override void OnBindablePropertySet(BindableProperty property, object original, object value, bool changed, bool willFirePropertyChanged)
+		{
+			base.OnBindablePropertySet(property, original, value, changed, willFirePropertyChanged);
+
+			// When the same CursorPosition or SelectionLength value is re-set, the bindable property
+			// system detects no change (changed=false) and does not fire PropertyChanged, so the
+			// handler mapper is never invoked. We force a handler update here so the native control
+			// always receives the selection state. This is required on WinUI where the native TextBox
+			// resets the caret position on each focus event.
+			if (!changed)
+			{
+				switch (property.PropertyName)
+				{
+					case nameof(CursorPosition):
+						Handler?.UpdateValue(nameof(CursorPosition));
+						break;
+					case nameof(SelectionLength):
+						Handler?.UpdateValue(nameof(SelectionLength));
+						break;
+				}
+			}
+		}
+
 		private protected override string GetDebuggerDisplay()
 		{
 			var debugText = DebuggerDisplayHelpers.GetDebugText(nameof(Text), Text);
diff --git a/src/Controls/tests/TestCases.HostApp/Issues/Issue23329.cs b/src/Controls/tests/TestCases.HostApp/Issues/Issue23329.cs
new file mode 100644
index 000000000000..d1cfc267e465
--- /dev/null
+++ b/src/Controls/tests/TestCases.HostApp/Issues/Issue23329.cs
@@ -0,0 +1,38 @@
+namespace Maui.Controls.Sample.Issues;
+
+[Issue(IssueTracker.Github, 23329, "Entry select all text on refocus does not work on WinUI", PlatformAffected.UWP)]
+public class Issue23329 : ContentPage
+{
+	readonly Entry _textBox;
+
+	public Issue23329()
+	{
+		_textBox = new Entry
+		{
+			AutomationId = "TextBox",
+			WidthRequest = 300
+		};
+		_textBox.Focused += OnTextBoxFocused;
+
+		var otherElement = new Button
+		{
+			AutomationId = "OtherElement",
+			Text = "Other",
+			WidthRequest = 128
+		};
+
+		Content = new VerticalStackLayout
+		{
+			Children = { _textBox, otherElement }
+		};
+	}
+
+	void OnTextBoxFocused(object sender, FocusEventArgs e)
+	{
+		if (_textBox.Text != null)
+		{
+			_textBox.CursorPosition = 0;
+			_textBox.SelectionLength = _textBox.Text.Length;
+		}
+	}
+}
diff --git a/src/Controls/tests/TestCases.Shared.Tests/Tests/Issues/Issue23329.cs b/src/Controls/tests/TestCases.Shared.Tests/Tests/Issues/Issue23329.cs
new file mode 100644
index 000000000000..ca876a7245c6
--- /dev/null
+++ b/src/Controls/tests/TestCases.Shared.Tests/Tests/Issues/Issue23329.cs
@@ -0,0 +1,44 @@
+#if WINDOWS
+using NUnit.Framework;
+using UITest.Appium;
+using UITest.Core;
+
+namespace Microsoft.Maui.TestCases.Tests.Issues;
+
+public class Issue23329 : _IssuesUITest
+{
+	public Issue23329(TestDevice device)
+		: base(device)
+	{ }
+
+	public override string Issue => "Entry select all text on refocus does not work on WinUI";
+
+	[Test]
+	[Category(UITestCategories.Entry)]
+	public void EntrySelectAllOnRefocusReplacesText()
+	{
+		App.WaitForElement("TextBox");
+		App.Click("TextBox");
+		App.EnterText("TextBox", "Hello");
+
+		// Blur and refocus twice. The second refocus is where the bug manifests:
+		// the Focused handler re-applies the same CursorPosition / SelectionLength
+		// values, so the bindable property change tracking would skip propagation
+		// to the native TextBox unless the InputView / TextBoxExtensions fix forces
+		// a handler update for unchanged values.
+		App.Click("OtherElement");
+		App.Click("TextBox");
+		App.Click("OtherElement");
+		App.Click("TextBox");
+
+		// If select-all worked on the second refocus, typing 'X' replaces the
+		// entire selected text, so the Entry ends up containing just "X". If the
+		// bug is still present, 'X' is inserted at the native caret position
+		// (wherever the click landed in "Hello"), producing something like "HelloX".
+		App.EnterText("TextBox", "X");
+
+		var text = App.FindElement("TextBox").GetText();
+		Assert.That(text, Is.EqualTo("X"));
+	}
+}
+#endif
diff --git a/src/Core/src/Platform/Windows/TextBoxExtensions.cs b/src/Core/src/Platform/Windows/TextBoxExtensions.cs
index 1f3e20620a18..f57fb5b97701 100644
--- a/src/Core/src/Platform/Windows/TextBoxExtensions.cs
+++ b/src/Core/src/Platform/Windows/TextBoxExtensions.cs
@@ -224,7 +224,13 @@ public static void UpdateVerticalTextAlignment(this TextBox textBox, ITextAlignm
 		public static void UpdateCursorPosition(this TextBox textBox, ITextInput entry)
 		{
 			// It seems that the TextBox does not limit the CursorPosition to the Text.Length natively
-			entry.CursorPosition = Math.Min(entry.CursorPosition, textBox.Text.Length);
+			var clampedPos = Math.Min(entry.CursorPosition, textBox.Text.Length);
+
+			// Only write back the clamped value when it actually differs. An unconditional write
+			// would re-enter InputView.OnBindablePropertySet → Handler.UpdateValue in an infinite loop
+			// because that override now forces handler updates even when the value hasn't changed.
+			if (entry.CursorPosition != clampedPos)
+				entry.CursorPosition = clampedPos;
 
 			if (textBox.SelectionStart != entry.CursorPosition)
 				textBox.SelectionStart = entry.CursorPosition;
@@ -233,7 +239,12 @@ public static void UpdateCursorPosition(this TextBox textBox, ITextInput entry)
 		public static void UpdateSelectionLength(this TextBox textBox, ITextInput entry)
 		{
 			// It seems that the TextBox does not limit the SelectionLength to the Text.Length natively
-			entry.SelectionLength = Math.Min(entry.SelectionLength, textBox.Text.Length - textBox.SelectionStart);
+			var clampedLen = Math.Min(entry.SelectionLength, textBox.Text.Length - textBox.SelectionStart);
+
+			// Only write back the clamped value when it actually differs — see UpdateCursorPosition
+			// comment above for the re-entry rationale.
+			if (entry.SelectionLength != clampedLen)
+				entry.SelectionLength = clampedLen;
 
 			if (textBox.SelectionLength != entry.SelectionLength)
 				textBox.SelectionLength = entry.SelectionLength;