The old Benedictine and Cistercian monasteries of Western Europe faced new testing economic conditions by the late Middle Ages. Gifts and donations to the institutions had dried up, the manorial system and serfdom were on the wane, and furthermore, these old monasteries faced competition from new private and charitable foundations such as hospitals and mendicant houses. Many monasteries fell into economic decline as a result, suffering from a crisis in liquidity and from expropriation of their lands. Was this decline inevitable or avoidable, however? By focusing on some cases of institutional adaptation in the Low Countries and Italy, it is shown that these older monasteries could adapt and reinvent themselves to stave off crisis. However, as is later revealed, not all monasteries encountered the same favourable power and property constellations necessary to achieve the required levels of institutional flexibility.