Language brokering remains prevalent among immigrant families, but it is widely assumed that brokering functions as a cultural stressor, resulting in adverse health outcomes for immigrant youth. Few studies, however, have tested this assumption, particularly while using longitudinal data and capturing multiple dimensions of brokering. Thus, this study examined how depressive symptoms and family-based acculturation stress mediated the relationships between various aspects of brokering (i.e., frequency of brokering, positive and negative feelings about brokering, brokering norms, and brokering efficacy) and alcohol, cigarette, and marijuana use and other risky behaviors. Using longitudinal survey data from 234 Latino early adolescents in 6th-8th grades (M age = 12.4 years; Females = 46.2 %), brokering for parents indirectly affected alcohol and marijuana use through family-based acculturation stress; however, these significant indirect effects became non-significant when taking into account negative brokering feelings and brokering as a burden on one's time. Feeling positively or efficacious about brokering or having pro-brokering norms did not directly predict any adverse mental and behavioral health outcomes. Moderation analyses, however, revealed that brokering for parents did not seem to function as a stressor when Latino early adolescents were high in brokering efficacy (e.g., feeling confident in one's ability to broker) or descriptive brokering norms (e.g., perceiving one's peers as brokering often). By contrast, when Latino early adolescents perceived brokering as a burden, brokering for parents functioned as a stressor, placing Latino early adolescents at risk for family-based acculturation stress, and in turn, alcohol and marijuana use. Such findings point to the complexity of brokering.