The most prominent figure among the medieval Iberian Encaoua is Rav Yitzhak Ben Choushan Encaoua, whose responsa exerted a considerable influence in the thirteenth century.
His writings are preserved at the Bibliothèque nationale de France (Hebrew collection, ms. 389) and at the National Library of Spain. He was a disciple of the Meïri of Perpignan and corresponded with the Rashba of Barcelona.
The Takkanot of Valladolid of 1432 bear the signature of several rabbis, among them a certain Shem Tov Encaoua, representative of the communities of Andalusia. The Takkanot of Valladolid were one of the most important rabbinic congresses of Iberian Judaism. Bringing together delegates from all the communities of Castile, they codified rules of communal taxation, education, and rabbinic jurisdiction. The presence of an Encaoua among the signatories confirms the family's role in the highest legal bodies of Spanish Judaism, half a century before the expulsion.
He wrote a partial commentary on the Moreh Nevukhim (Guide for the Perplexed) of Maimonides, fragments of which are preserved in Hebrew codex 419 of the Vatican Library. This commentary belongs to the tradition of the Maimonidean super-commentaries that flourished in Spain in the thirteenth and fourteenth centuries, a period when the work of Maimonides aroused impassioned debates between rationalists and mystics. The Moreh Nevukhim, composed in Arabic around 1190, sought to reconcile Aristotelian philosophy with the Torah — an intellectual project that the Encaoua of the following generations would take up in their turn, notably Éphraïm Al-Naqua in the Sha'ar Kevod Hashem.
To understand the place of the Encaoua in the medieval rabbinic landscape, one must situate them within the intellectual ecosystem of Jewish Spain in the thirteenth and fourteenth centuries. The great talmudic academies of Toledo, Barcelona, Perpignan, and Girona formed a dense network of scholars in constant correspondence. The Meïri of Perpignan (1249–1315), who was one of the teachers of Rav Yitzhak Ben Choushan Encaoua, embodied an open and rationalist approach to Halakha. The Rashba of Barcelona (1235–1310), correspondent of the Encaoua, represented for his part a more mystical current, influenced by Provençal Kabbalah. The Encaoua navigated between these two poles, as heirs of a Castilian tradition that favored synthesis over polemic.