After the war, Osborne retired from the Diplomatic Service and settled in Italy, living at the Palazzo Sacchetti, 66 Via Giulia, Rome. With the future Pope Paul VI, whom he had befriended during the war, he founded an industrial school for the poor boys of Rome. He was visited by The Queen and The Queen Mother on several occasions. His financial situation remained precarious, and in 1962 a group of friends, including The Queen Mother, arranged a sum of money for his relief.