Today, if you ask any Roman Catholic or Anglican priest about their parishioners’ frequency of practicing confession, he or she would almost certainly tell you that there has been a decline in the number of those who come to the confessional. Statistical research from one Georgetown report supports this observation of the decline of confession in the church (Gray and Perl 2008). While ecclesial confessions are certainly performed by fewer and fewer people, digital technology has opened the floodgates to a new kind of anonymous confession. This paper seeks to thicken our conception of the study of religion through a re-imagination of religious scholarship in a digital age. The first section of this essay will address the problem that anonymity and automation prevents data in the digital sphere from necessarily corresponding to activity in the physical sphere within which human beings live, breath, talk, and act. Next, we will examine possible solutions to this problem of mapping humans to digital activity. To ground theory in practice, we will explore the way forward through an analysis of digital confessions through the lens of Foucauldian power structures and media effects. As Christianity plunges further into a digitally-saturated environment, pastors and theologians alike must take heed of the changing landscape of confession, remaining ever aware of the Church body’s psychological, pastoral, and theological needs.