The parent of an already removed span cannot be found and a NullReferenceException is thrown while performing Undo. Also, multiple asserts are failing in Debug mode. The stack trace is: UnhandledException: Object reference not set to an instance of an object. UnhandledException: at Telerik.Windows.Documents.Layout.LayoutElement.SetParent(LayoutElement newParent) at Telerik.Windows.Documents.Layout.LayoutBox.EnsureParent() at Telerik.Windows.Documents.Layout.LayoutBox.get_Parent() at Telerik.Windows.Documents.Layout.LayoutBox.get_ValidParent() at Telerik.Windows.Documents.WordPositionHandler.GetParentHandler() at Telerik.Windows.Documents.DocumentPosition.GetCurrentSectionBox() at Telerik.Windows.Documents.UI.DocumentPrintLayoutPresenter.GetCurrentPage() at Telerik.Windows.Documents.UI.DocumentPrintLayoutPresenter.MeasureOverride(Size availableSize) at System.Windows.FrameworkElement.MeasureCore(Size availableSize)