This article highlights the experiences of the first Japanese students at Massachusetts Institute of Technology (MIT) by analyzing archival sources in the MIT Libraries Distinctive Collections that are connected to MIT’s first two Japanese graduates, Honma Eiichirō and Dan Takuma. These documents not only provide firsthand accounts of Honma and Dan’s studies in the United States but also offer rich details regarding the community of fellow Japanese students around them in Boston. Notably, they provide examples of both instances in which attitudes and relationships particular to these students’ samurai identity continued to shape their experiences in the United States, on the one hand, as well as those in which they attempted to distance themselves from such continuities, on the other. What becomes especially clear in these documents are the ways in which Honma, Dan, and other Japanese students in Boston during the 1870s understood their experiences as steps that would lead to their future careers not only as professionals in specific fields but also as members of a newly emerging elite that would be responsible for shaping their country’s modern transformation.