Contradictions abound in remedial higher education. While 40% of American undergraduate students take remedial coursework (Attewell et al., 2006), remediation represents just one percent of the national higher education budget (Handel & Williams, 2011). Furthermore, the status quo in remedial teaching and learning in American higher education does not appear to be successful at actually remediating students and aiding in their completion of degrees (Attewell et al., 2006). This essay argues for a more holistic approach to working with underprepared students than the all-too-common deficit-based approach allows for and presents a first-person practitioner's account of a reflective-thinking classroom ritual based on the spiritual discipline of the Ignatian Examen as a paradigmatic example of a holistic approach that accounts for the developmental as well as the sociopolitical realities of under-prepared students. The essay also identifies an amicable confluence of ideals and methods among Ignatian pedagogy, critical pedagogy, and liberation theology. (Contains 2 notes.)