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Critical hope plays a vital role in understanding one’s environment and opportunities and fosters individual growth and community well-being, particularly for students facing marginalization and systemic oppression (Duncan-Andrade, 2009; Ginwright, 2016). In this qualitative study, we examined the future self-planning narratives of high school boys attending an alternative learning environment in eastern Alabama. To better understand the participants’ experiences, we applied Duncan-Andrade’s (2009) theoretical framework of critical hope to interpreting our data. The findings indicate that alternative school students’ experiences in punitive and restrictive environments ultimately influence what they see as possible for their futures.