The priory became known for its strict observance of the Augustinian rule and religious precepts. Its reputation for ducentes canonicam vitam ("living a canonical life") attracted Saint Malachy from Ireland who, as Saint Bernard of Clairvaux had a long and close involvement with Gisborough. The canons were closely associated with the Cistercians who, like the Augustianians, had a reformist outlook. One Gisborough canon, William of Newminster, moved to the Cistercian Fountains Abbey to become its abbot. The priory was supported by the local people and records survive of numerous small grants, related to the almonry (the place or chamber where alms were distributed to the poor) and to support building work. The canons leased, bought and sold land and loaned money using property grants as collateral to benefit the priory's building fund. As the priory became more wealthy, discipline among its canons slipped and the Archbishops of York found it necessary to take corrective action in the late 13th century. A number of canons were sent to Kirkham and Bridlington for correction and Gisborough in turn took in disobedient canons from other places. The priory also became embroiled in a dispute with a local landowner, Robert de Thweng, who raided its properties and tithe barns in 1232 under the alias of "Will Wither", in the course of a dispute with the priory over the advowson of Kirkleatham parish church.
The priory became known for its strict observance of the Augustinian rule and religious precepts. Its reputation for ducentes canonicam vitam ("living a canonical life") attracted Saint Malachy from Ireland who, as Saint Bernard of Clairvaux had a long and close involvement with Gisborough. The canons were closely associated with the Cistercians who, like the Augustianians, had a reformist outlook. One Gisborough canon William of Newminster, moved to the Cistercian Fountains Abbey to become its abbot. The priory was supported by the local people and records survive of numerous small grants, related to the almonry (the place or chamber where alms were distributed to the poor) and to support building work The canons leased, bought and sold land and loaned money using property grants as collateral to benefit the priory's building fund. As the priory became more wealthy, discipline among its canons slipped and the Archbishops of York found it necessary to take corrective action in the late 13th century. A number of canons were sent to Kirkham and Bridlington for correction and Gisborough in turn took in disobedient canons from other places. The priory also became embroiled in a dispute with a local landowner, Robert de Thweng, who raided its properties and tithe barns in 1232 under the alias of "Will Wither", in the course of a dispute with the priory over the advowson of Kirkleatham parish church.