A key aspect of the theological anthropologies of both Augustine and Maximus Confessor is the notion of a divided and reunited self. For Augustine, the fallen human will is divided against itself, ensnared in old habit, and unable to will the good, a condition that Augustine famously depicts in the Confessions and which he elaborates in more fragmentary ways elsewhere. For Maximus, the fallen will is gnomic, torn between varying choices and subject to the bondage of sin, and humankind lives in a condition of fragmentation on multiple levels, awaiting the unification of the soul’s various syzygies that comes with deification, which is itself a serious of ascending unities through participation in Christ (Russell 2004). This short communication will offer an initial comparison of the psychologies of Augustine and Maximus with respect to the division and reunification of the human mind and soul, building on recent work on Augustine by scholars such as Donald Capps (2007, etc.), James Wetzel (2008, etc.), Jean-Luc Marion (2008/2012), Johannes Brachtendorf (2000, 2009), and William Parsons (2013), and on Maximus by the likes of Lars Thunberg (1995), Jean-Claude Larchet (1996), Ian McFarland (2005, 2007), George Berthold (2011), Michael Bakker (2013), and Paul Blowers (2011, 2012). It will give particular attention to their understandings of unconscious versus conscious willing, the force of habit and the passions, and the nature of psychological integration, and it will briefly identify how the psychologies of each author relate to their doctrines of Christ, the Holy Spirit, and eschatological fulfillment.