Underachievement among gifted students is a paradox that frustrates educators because of the significant disparity between students' potential and their performance. Complicating the issue is the highly individualized nature of the underperformance, which must take into consideration factors of student culture, socio-economic status, motivation, and the environment. Once these factors are considered, both the intellectual and affective needs of the gifted underachiever must be examined and supported in order to try and bridge the gap between known ability and actual performance. This case study examines the factors behind three gifted underachievers in an urban, high school setting. Through interviews and observation, the researcher sheds light on the potential influences of each individual's level of underachievement and shares insight into how it was addressed in the classroom through the lenses of motivation, culture and context, and the environment. While the approaches and outcomes for each student are different, one theme emerged: students were more effective at instituting change in their lives once they had fully accepted and embraced that they were both gifted and underachieving.