The first goal of this study was to investigate whether levels of overparenting behavior (anticipatory problem-solving, advice/affect management, tangible assistance, and low levels of child self-direction) differ depending on the context (Arab-Israeli vs. Jewish-Israeli; mothers vs. fathers). Second, we considered whether the association between overparenting and young adults’ interpersonal sensitivity depends on those contexts. Questionnaires were collected from 165 triads (mothers, fathers, and young adults), of which 89 were Jewish-Israeli and 76 Arab-Israeli. Parents reported on their overparenting behaviors and young adults reported on their interpersonal sensitivity. Results indicated that all four dimensions of overparenting behaviors were more prominent in Arab-Israeli culture than in Jewish-Israeli culture, while advice/affect management was lower for mothers than for fathers and fathers provided more child self-direction than mothers. In addition, higher levels of anticipatory problem-solving were significantly associated with higher levels of young adult interpersonal sensitivity, independent of parental gender or cultural background, supporting the general negative association between anticipatory problem-solving and interpersonal sensitivity.