DeleteAnnotationRange fails to execute when the content is uneditable annotation. For example: PermissionRange with a checkbox content control inside.
A possible workaround would be to manually delete the annotation range from the document element tree:
var rangeEnd = rangeStart.End;
var endParent = rangeEnd.Parent;
if (endParent != null)
{
endParent.Children.Remove(rangeEnd);
}
var parent = rangeStart.Parent;
if (parent != null)
{
parent.Children.Remove(rangeStart);
}
this.radRichTextBox.UpdateEditorLayout();