A substantial body of research has shown that academic intrinsic motivation/cognitive engagement decreases from grades three through eight (Lepper, Corpus, & Iyengar, 2005). This phenomenon is troubling if education is to be viewed as a process through which learning goals become gradually internalized and connected with one's sense of self. Although substantial research addresses motivational means through which achievement can be increased, few studies problematize the unintended consequences of these approaches. From a larger quantitative study of the relationship between engagement and achievement (5,392 students in grades 3-12), eight high-achieving, cognitively disengaged middle-school students were interviewed to understand their motivation toward learning. Classroom observations, teacher/principal interviews, and parent surveys contextualized the findings. Thematic analysis was organized according to the subscales of autonomy, competence, and relatedness, as described in self-determination theory (Deci & Ryan, 1985). Findings suggest that the student participants experienced a single-minded focus upon grades, which manifested itself through rigorous homework routines and academic competitiveness. In alignment with Baumrind's (1966) construct of authoritative parenting, participants described a gradual removal of parental supervision with respect to the students' academic responsibilities. This emergent trust in the students was based upon measurable academic success, rather than upon evidence of self-endorsed learning.