Raghnaill were allied to the Kildare camp the church may have given them preferential treatment. Reynolds graduated in Canon Law around 1531, and secured a grant of "English liberty" entitling him to acquire property and benefice in English Ireland. Archdeacon of Kells (1532–1534) On returning to Ireland, Reynolds became chaplain to Gerald FitzGerald, 9th Earl of Kildare, lord deputy of Ireland. The Fitzgerald dynasty was the most powerful family in Ireland. Reynolds was also appointed archdeacon of Kells and rector of Nobber on 13 Feb 1532. A canonist, he was very active as a diocesan and provincial administrator. His appointments came during a time of tremendous international change, and a dangerous time for Christendom. Reynolds soon became involved in huge political issues. Revolt against Henry VIII (1534–1535) During 1533, the political situation in Ireland and England was fraught with tension over Henry Tudor's English Reformation. The Irish Council in the Pale was dominated by rival Norman-Irish factions, and the only clerics trusted to promote the English Reformation in Ireland were three Englishmen, the most prominent being John Alen, Archbishop of Dublin. Rumours circulated that Charles V, Holy Roman Emperor, aggrieved by the treatment of his aunt, Catherine of Aragon, might intervene in Ireland. Thomas Cromwell, Henry's chief minister, decided to appoint an Englishman, William Skeffington as lord deputy in Ireland. The incumbent, Gerald Fitzgerald, was imprisoned in the Tower of London in spring 1534, provoking his son "Silken" Thomas to start the "Kildare rebellion". Charles V responded quickly to appeals for assistance by dispatching emissaries. The potential for a military intervention drew international attention on Ireland. Reynolds was a prominent member of a group of senior Irish clerics denouncing Henry as a heretic. These clerics shared a held belief English rule was empowered, under Laudabiliter-inspired papal sanction, to merely reform the Irish along conventional canonical lines only. Recognising the English revolution as fundamentally attacking the intellectual and legal basis for their canonical beliefs, they were spurred into revolt and radical action. They believed the King of England had rejected the papal authority and tradition upon which his sovereign rule in Ireland rested, therefore his authority had to be denied. Prospects for a successful rebellion receded, when a fleeing Archbishop John Alen was captured and killed by rebels. The Pope responded by excommunicating Silken Thomas. Reynolds was dispatched as an envoy abroad to pursue an alliance against Henry VIII of England,