Drawing on Cultural Historical Activity Theory, language socialization, and the notion of "third space," this article examines how bilingual, Latina/o students (Latina/o English learners) use sophisticated linguistic, cultural, and mathematical tools to solve community-based problems. This article examines the inherent tensions in using multiple linguistic tools to engage in a mathematically rich activity called "Recipes." Rather than view these tensions as impediments, this article conceptualizes the emergent tensions as pivotal for learning and development. This analysis is drawn from a larger cross-site collaboration of 2 after-school clubs located in the Midwestern and Southwestern parts of the United States. This article focuses on findings from the Midwestern, urban, after-school club where bilingualism was explicitly privileged in the context of activities. The findings suggest that when activities are open-ended, community-based, and designed to promote multiple modalities and mediational tools, students move beyond static learner roles and actively contest and persist in challenging problem-solving tasks.