The article explores the gendered imaginary in the Gnadenleben of Friedrich Sunder (1254–1328) and the formation of clerical masculinity in the context of feminine devotional life. Friedrich Sunder worked as a convent chaplain for a Dominican female community and lived within the convent's area. In his book Sunder employs language, images and devotional practices that can be considered in medieval culture to have been feminine. Almost simultaneously, however, he applied masculine roles and emphasised his own manliness. Although Sunder accepted female forms of religiosity and wrote on practices that were considered especially suitable for women, at the same time his priestly masculinity was defined by the physical boundary the cloister created between the enclosed feminine religiosity and that of a pastoral masculine priesthood. His discussion of gender within the mystical frame defined the boundaries of his own masculinity in the web of different traditions of both the proper way of life and the gendered nature of religious practices.