Students learning English at school and another language at home comprise a rapidly growing segment of U.S. student populations. Language learners can benefit from using technology, but do not always use it advantageously (Katz & Gonzalez, 2016). Many studies address technology's scholastic use, but few investigate how bilinguals use digital technology at home (Hinostroza, Matamala, Labbé, Claro, & Cabello, 2015), or what it means to them (Toboso-Martin, 2013). This qualitative multiple-case study focuses on the intersection between bilinguals, intergenerational learning, and digital technology. Specifically, it studies how bilingual, Hispanic family members interact around information and communication technology (ICT), and their attitudes toward ICT. Language patterns emerged during paired ICT use. Data were gathered from six Hispanic, bilingual families in the Midwestern U.S. through interviews, observation, and tasks where intergenerational pairs were asked to teach each other about ICT. This study adds to the literature on bilingualism, digital literacy, sociocultural theory, and intergenerational learning. Findings included parental ICT policies of vigilance, access, and trust. Findings support arguments that the digital divide persists as digital literacy. ICT both impeded and promoted intergenerational learning. Findings shed light on bilinguals' contextualized linguistic needs, and echoed Vygotsky's writings on gesture, internalized speech, and serial thought processing. English dominated as the language of ICT, but participants used Spanish and English to contextualize problems and negotiate meaning. Findings affirmed factors affecting the quality of ICT use. The author argues that v Grosjean's Complementarity Principle can be applied to digital literacy. Implications for parents, teachers, and researchers are given.