The KeyUp/KeyDown events sometimes are not triggered when using Keyboard.Modifiers. The issue can be reproduces if the keyboard key combination is pressed quickly. Useful case where using those modifiers is when the desired behavior is to restrict the Ctrl+Z (undo command) in the RadWatermarkTextBox control.
This is a framework issue in Silverlight. The same problem occurs with a normal TextBox and handler to its KeyDown event. The framework doesn't send correct e.Key in the arguments when ctrl+z is pressed. It sends "Control" as key instead of "Z". The workaround is to create a custom RadWatermarkTextBox: public class CustomWatermark : RadWatermarkTextBox { protected override void OnKeyDown(KeyEventArgs e) { if ((ModifierKeys.Control == Keyboard.Modifiers) && e.Key == Key.Z) { e.Handled = true; return; } base.OnKeyDown(e); } }