I have issues with Databindings for RadToggleButton and RadDock ToolWindow. Here are 3 scenarios to try with my repro application. ToggleButton Click the radToggleButtonElement1, notice that the binding never occurs. ToolWindow Docking issue 1 Dock the toolWindow1 to the left over ToolWindow2 Click toolWindow2 Click toolWindow1 Click toolWindow2 Notice each time you click another tool window, the binding is triggered even if the property value hasn't changed. ToolWindow Dockin issue 2 Dock the toolWindow1 to the left over toolWindow2 Notice that the binding is triggered, but with the previous value (Floating instead of Docked) close the toolWindow1 Notice that the binding is triggered, but with the previous value (Docked instead of Hidden)