This essay investigates the spiritual mentorship of Doña Sancha Carrillo (1513–37) by Juan de Ávila (1499–1569). The relationship shaped Carrillo’s self-reliance and Ávila’s identity as educator, writer, and counselor. I uncover unexamined ways in which Carrillo, with Ávila’s help, plotted a path of increasing spiritual autonomy by applying the lessons that he taught her: learning to control her visions, quell her desires, counsel others, and harness her senses to achieve heightened spirituality. Contrary to conventional accounts that briefly note Ávila’s tutelage of Carrillo, this essay argues that the relationship profoundly affected Ávila when he emerged as a leader of Christian life in Andalusia, during an important transitional age for the region after the Reconquest and before the Counter Reformation. I demonstrate how Ávila’s schools and apostolate bear the imprint of Carrillo because he developed pedagogies with her that he later applied broadly. This essay also sheds light on the possibilities and representations of women’s religious practices in early sixteenth-century Andalusia, both of which changed after Trent’s directives and affected treatment of Carrillo’s story. First I lay out information about Ávila and the spiritual program that he developed for Carrillo. Then I analyze evidence that shows how this curriculum fostered autonomy for Carrillo, allowing her to advise others in accordance with Ávila’s way. This essay builds from secondary observations of Carrillo’s practices and intellect to primary evidence from her letter and visions, revealing the bidirectional nature of the influence between guide and mentee and its effects on the greater community.