This cross-cultural study investigates how maternal task assignment relates to toddlers' requested behavior and helping between 18 and 30 months. One hundred seven mother-child dyads were assessed in three different cultural contexts (rural Brazil, urban Germany, and urban Brazil). Brazilian mothers showed assertive scaffolding (serious and insistent requesting), whereas German mothers employed deliberate scaffolding (asking, pleading, and giving explanations). Assertive scaffolding related to toddlers' requested behavior in all samples. Importantly, assertive scaffolding was associated with toddlers' helping in rural Brazil, whereas mothers' deliberate scaffolding related to toddlers' helping behavior in urban Germany. These findings highlight the role of caregivers' socialization practices for the early ontogeny of helping behavior and suggest culture-specific developmental pathways along the lines of interpersonal responsibility and personal choice.