This article analyzes the context and content of a manuscript written by a Perugian nun overseeing the regularization of a group of Franciscan tertiaries into the second order convent of S. Sebastiano in Borgo San Sepolcro in 1500. This narrative allows the “other voice,” the voice of the nun, to be heard, but this female voice has a strong agenda, and in its turn blocks the voices of the third-order women. Close reading of the manuscript provides the opportunity to examine the process of regularization by assessing not only the separate roles of the women from Perugia supervising the enclosure and the women, mainly from Borgo San Sepolcro, being newly enclosed, but also the different roles assigned to women and men in the multiple layers of the ecclesiastical hierarchy. The account suggests that certain second-order nuns acted in conjunction with sections of the male ecclesiastical hierarchy and the secular authorities to carry out the regularization.