While US and Dominican officials have traditionally received credit for the expansion of the public school system during the US military occupation of the Dominican Republic from 1916 to 1924, this article offers an alternative account by focusing on the role of guardians, or caretakers, in supporting and creating schools in this period. Drawing from sources from the Department of Public Instruction in the Dominican Republic and analyzing them “against the archival grain,” I argue that Dominican guardians were pivotal to the expansion of the Dominican school system and key actors in shaping the educational landscape during this period. Not only did guardians construct and maintain most of the schools opened during the US occupation, but they also shaped school policy. Most significantly, through their grassroots efforts, guardians and other volunteers ensured that schools in the Dominican Republic continued to operate during the financial crisis of 1921 that bankrupted the school system.