This phenomenological case study explores the persistence of high school readers labeled as struggling as they described their responses to recurring, consistent, externally originating challenges to positive reading identities growing from their experiences in a Young Adult Literature (YAL) course. Through application of Weinreich’s identity theory, the article examines three challenges that emerged: the home environment, friend influence, and school norms and practices. Findings drawn from student-generated oral reflections gathered through Seidman’s interview protocol suggest that participants possessed the power to dissociate from perceived negative reading identities and enact agency over identities that conflicted with their desired reading identities. However, participants were particularly vulnerable to the influence of school-ascribed reading identities they defined as negative. Given the perceived validity of these ascribed labels, readers were challenged more significantly in their attempts to persist in the self-construal of their desired identity conceptions in response to in-school, rather than out-of-school, challenges.