As a young man, Raymond felt a religious vocation, and became a canon of the new cathedral at Tarazona, established after King Alfonso I of Aragon reconquered the historic city from the Moors in 1119.

Across the Pyrenees mountains, at Escaladieu Abbey in Gascony, Raymond became a monk of the Cistercian Order, which had been founded relatively recently (in 1098) and which accepted many former knights as members.

In Toledo Raymond's companion, former knight Father Diego Velásquez, learned that Christian leaders planned a major offensive south against the Moors.

With the support of the Archbishop of Toledo, Raymond organized an army that successfully prevented a Moorish attack on Calatrava that year.

Raymond then moved some fighting monks south from the relatively safe Fitero in Navarre to Calatrava in what became the Castilla-La Mancha province.