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This article reports from five years of qualitative research into the languages and literacies of language brokers during tutoring sessions between emergent bilingual elementary school students, their mothers, and homework mentors at an after-school program in New York City. Alvarez’s research explores the translanguaging practices (García, 2009; 2012) of participant youth language brokers who simultaneously translated and interpreted homework with adults. He examines translanguaging events during homework tutoring, documenting how practices such as language brokering develop tactical repertoires for youths communicating language arts assignments between their mothers, mentors, and peers. Emergent bilingual youth and their homework mentors at the after-school program involved Spanish-dominant mothers in English language activities, permitting mothers’ increased collaboration in their children’s homework assignments. Together, families and mentors worked to pool their bilingual resources in the practices of doing monolingualized homework multilingually and with meaningful involvement.