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For the past forty years moral theology has understood its history to be very much rooted in the early medieval penitential manuals. In this lecture James F. Keenan, S.J. argues that those manuals were rooted, not simply in a confessional practice, but much more in the context of what today we would call spiritual direction. Monks and nuns were primarily not focusing on their sins but rather on pursuing holiness. With that key insight we look to the earlier history of moral theology and find pathways to holiness as a worthy key to understanding Christian expectations.