This ethnographic study explores what happens in the lives of two 1.5-generation undocumented Latino youth that results in academic engagement or disengagement. It examines how turning points, policy, language proficiency, school structure, economic needs, and family and personal circumstances affect academic identities. Findings reveal how students' agency can make a big difference in explaining the high school graduation of youth who are proficient in English. Consequently, labeling students as low or high achievers disregards the fluidity of their academic identities as well as their capacity to change their academic trajectories within society's structural limitations.