The Benedictine priory at Littlemore was founded in the 12th century by Robert de Sandford in the latter years of the reign of King Stephen. Always a small house, from around 1245 the priory's history is obscure, going unmentioned in both episcopal and government records. By the later Middle Ages, it was reported that the seven nuns of Littlemore were not living according to their rule. In 1445 the priory was visited by agents of William Alnwick, Bishop of Lincoln. Following their inspection, they reported the nuns failed to fast and ate meat every day. Furthermore, the prioress, Alice Wakeley, regularly received a Cistercian monk and a lay clerk in her rooms to indulge in drinking sessions. There was much local gossip, and it appears to have been common knowledge that the nuns shared beds, apparently because the main dormer was structurally unsafe. The bishop instructed that the nuns were to use separate beds, and that no lay persons, "especially scholars of Oxford", were to be allowed admittance to the priory. By the early years of the 16th century, the congregation had been reduced to a prioress and five nuns; three of these, Elizabeth, Joan and Juliana, were sisters surnamed Wynter. On 17 June 1517 Littlemore Priory was visited by Edmund Horde, a commissary of Bishop William Atwater of Lincoln, accompanied by the episcopal chancellor, Richard Roston. The reasons for his visit are unknown, although Eileen Power suggests that around this time, Atwater "had awakened to the moral condition of Littlemore". Horde's subsequent comperta, which were presented as findings of fact and were effectively accusations, were comprehensive. Firstly, he suggested that the nuns had lied to him on their prioress's orders from the moment he arrived. They had told him all was well, "omnia bene", [within Littlemore; he discovered that this was not the case. Investigators such as Horde were expected to be thorough, "examining each member of the house, going into the minutest details, and taking great pains to arrive at the truth".
Horde reported that the prioress, Katherine Wells, had had an illegitimate daughter by Richard Hewes, a chaplain from Kent, who was probably responsible for the priory's sacraments. Thomson suggests that this had clearly happened some years earlier, but had been either "concealed or deliberately overlooked by the authorities". The nuns said that Hewes still visited two or three times a year and was due again in early August. While he was there, Hewes and Wells lived as a couple, and their child dwelt among the nuns. Horde wrote that Wells, intending her daughter to make a good marriage, had stolen Littlemore's "pannes, pottes, candilsticks, basynes, shetts, pellous federe bedds" and other furniture from the common store for the girl's dowry.