In July 1659 there took place a conversation between Sir Henry Bennet and the papal nuncio in Madrid. From the latter’s evidence, it appears that Bennet claimed that he had been advising the English king in exile that the Civil Wars and execution of his father had been divine punishments for the mistakes of his ancestors, and that the only way to restore peace and good order in England would be through the re-establishment of the old religion. In other words, Charles II’s ambassador was indicating that his master’s future lay in the hands of the pope. This extraordinary encounter offers a context within which to consider some broader aspects of the lead-up to the Restoration. The late 1650s were years when it seemed as though the Stuart court in exile was turning Catholic. The earls of Inchiquin and Bristol had converted, and many believed that James was of like mind. Bennet had himself for some years been advocating closer ties with Rome, and his remarks to the nuncio at the Spanish court can be seen as an initiative running in parallel with approaches being made on behalf of Charles II by Cardinal de Retz. Bennet was also one of the few foreign diplomats who accompanied don Luis de Haro to the Pyrenees where he was treated with considerable honour, whilst Charles II’s brief visit to Spain in the autumn of 1659 was heartily welcomed by the Spaniards. They had already been making a sudden show of generosity in the provision of pensions and subsidies. They also offered to make the duke of York supreme commander of their fleets, and were taking notice of his recommendations for ecclesiastical appointments. This chapter will use primary sources from archives in England, Spain and Italy in order to throw new light on Sir Henry Bennet’s early career, and on the Catholic sympathies of the Stuart court in exile. It will also tie in with existing published work by F.J. Routledge, John Miller and Mark Williams.