Despite remaining neutral in the wars between France and the Holy Roman Empire, Antoine sent his son Francis to the French court and by 1527 was attempting to marry him to Anne of Cleves. In an effort to improve his relations with German lords, Antoine sent a few hundred soldiers to fight against the Ottomans at the Siege of Vienna in 1529. Antoine dispatched legal envoys to the Imperial diet, in 1532, seeking clarification of the duchy of Lorraine's legal status within the Holy Roman Empire to no avail.