This article explores the strategies that three Latino families in the U.S. employed in raising their children bilingually in Spanish and English. It also looks at their rationale for bilingualism as well as the challenges the parents failed to anticipate in implementing their strategies. The data were gleaned from comparative case studies over a three year period. The families wanted their children to be bilingual because they believed in the cognitive and economic advantages of bilingualism and that bilingualism would help maintain the families' roots. To maintain the native language, the families planned to speak and support the Spanish language at home and relegated the teaching of English to the school. While two of the families expressed concerns about their children not being proficient in English by the time they entered school, only one of the families anticipated some of the challenges that their daughter would face in learning and maintaining Spanish. In fact, the results of the study indicated that attaining productive bilingualism (the ability to speak the minority language) presented the three young girls with more difficulties than being proficient in English. Recommendations for parents and schools are provided.