As subjects of numerous studies and research reports since the 1930s, Puerto Ricans in U.S. mainland schools have been portrayed as problems, as losers or disadvantaged, and as potentially at risk. This chapter documents the difficult educational history of Puerto Ricans, who have been in U.S.-controlled schools even in Puerto Rico since 1898, to understand the impacts of their experiences and reasons for it, and to explore some possible solutions. Three persistent dilemmas related to the topic that must be acknowledged are the issue of appropriate ethnic labels, the inconsistency of data available about Puerto Ricans, and the dropout crisis. Three themes have characterized the Puerto Rican educational experience: (1) the legacy of colonialism; (2) the roles of racism, ethnocentrism, and linguicism; and (3) the quest for self-determination. Schools must be made more accommodating to the needs of Puerto Rican students and must acknowledge the importance of linguistic and cultural maintenance. (Contains 126 references.) (SLD)