This case study sought to identify factors that adversely affect meaningful learning in two African-American female high school students. Tanisha and Latanya are motivated, confident students in an urban, public half-day school for math and science ('Sci High'). Observations of classrooms at Sci High and their home schools, analysis of learning artifacts, school statistics and student records, clinical interviews with the students and interviews with teachers and administrators provided evidence of a lack of metacognitive awareness and realistic self-appraisal. The emerging themes indicate a cycle of cognitive disengagement that is perpetuated by complex cultural factors that permit cognitive passivity, generic motivation (or confidence-without-competence), and attention to behaviour over learning. It appears that without cognitive engagement, neither intentional, meaningful learning nor metacognitive awareness can develop. The findings are presented in an analogical graphic summary that facilitates discussion and analysis.