In conversation with Bruce Morrill’s article, the author explores how the fundamental ecclesiologies of Monika Hellwig and John Paul II influence their theologies of the sacrament of penance. John Paul’s ahistorical ecclesiology leads to distress around the collapse of confession and to increased clericalism, and his millennial apologies for ecclesial sins raise further questions regarding collective confession of fault. The author concludes by arguing that the absence of forms of individual and communal reconciliation undermines the church’s mission.