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Scholars have proposed that immigrant optimism explains why some immigrant students outperform their US-born peers academically. Yet, immigrant optimism has not been directly measured. The goal of this study is to test the immigrant optimism hypothesis by operationalizing it using the Children’s Hope Scale. Using structural equation modeling, the author examined the relationships between hope, immigrant generation, documentation status, and academic outcomes among a sample of 2,369 Latino 14-17-year-old students. Though no difference by immigrant generation was found, undocumented students were more hopeful than documented students. This finding suggests documentation status has an indirect relative effect on academic outcomes via hope. This article reexamines immigrant optimism as a resource that could be fostered among Latino youth, regardless of immigrant status.