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