diff --git a/src/Controls/tests/DeviceTests/Elements/Entry/EntryTests.Windows.cs b/src/Controls/tests/DeviceTests/Elements/Entry/EntryTests.Windows.cs
index d86cb99da135..61118bec0daf 100644
--- a/src/Controls/tests/DeviceTests/Elements/Entry/EntryTests.Windows.cs
+++ b/src/Controls/tests/DeviceTests/Elements/Entry/EntryTests.Windows.cs
@@ -112,5 +112,31 @@ await InvokeOnMainThreadAsync(() =>
 				Assert.Equal(new string('●', entry.Text.Length), passwordTextBox.Text);
 			});
 		}
+
+		[Fact]
+		[Description("Password entry should not crash when platform text is set from empty")]
+		public async Task PasswordEntryPlatformSetDoesNotCrash()
+		{
+			var entry = new Entry
+			{
+				Text = string.Empty,
+				IsPassword = true
+			};
+
+			var handler = await CreateHandlerAsync<EntryHandler>(entry);
+
+			await InvokeOnMainThreadAsync(() =>
+			{
+				var platformControl = GetPlatformControl(handler);
+				var passwordTextBox = platformControl as Microsoft.Maui.Platform.MauiPasswordTextBox;
+
+				Assert.NotNull(passwordTextBox);
+				Assert.True(passwordTextBox.IsPassword);
+
+				// Setting Text on an empty password entry triggers TextChanging event which previously threw ArgumentOutOfRangeException
+				passwordTextBox.Text = "test";
+				Assert.Equal("test", passwordTextBox.Text);
+			});
+		}
 	}
 }
diff --git a/src/Core/src/Platform/Windows/MauiPasswordTextBox.cs b/src/Core/src/Platform/Windows/MauiPasswordTextBox.cs
index b68052c54995..d4be871d62f6 100644
--- a/src/Core/src/Platform/Windows/MauiPasswordTextBox.cs
+++ b/src/Core/src/Platform/Windows/MauiPasswordTextBox.cs
@@ -328,7 +328,7 @@ static string DetermineTextFromPassword(string realText, int start, string passw
 
 			var lengthDifference = passwordText.Length - realText.Length;
 			if (lengthDifference > 0)
-				realText = realText.Insert(start - lengthDifference, new string(ObfuscationCharacter, lengthDifference));
+				realText = realText.Insert(Math.Max(0, start - lengthDifference), new string(ObfuscationCharacter, lengthDifference));
 			else if (lengthDifference < 0)
 				realText = realText.Remove(start, -lengthDifference);