This study evaluated the associations between adolescent individuation and concurrent and long term adjustment in adoptive families. Individuation was assessed using an observational measure examining behaviors and communications demonstrative of individuality and connectedness between each parent and the adolescent. Findings did not support the hypothesized connection between adolescent individuation and concurrent and long term adjustment in adoptive families. However, further analyses revealed particular importance of connectedness between adolescent and parent for adolescent adjustment, which was found to vary by adolescent gender. Specifically, analyses revealed that gender interacts with both adolescent-father connectedness and mother-adolescent connectedness in predicting adolescent internalizing symptoms; for adolescent males, internalizing symptoms were found to decrease as mother-adolescent connectedness increases. These findings suggest a shift in the understanding of individuated parent-adolescent relationships from comprising co-existing individuality and connectedness to connected relationships which allow for, support, and foster adolescent individuality and autonomy. These results also highlight the particular value of the mother-adolescent relationship for adolescent adjustment in adoptive families. Additionally, cross-informant ratings of adolescent and young adult adjustment were examined within and across time in this adoptive family sample. These findings are compared to relevant literature in adolescence and extend the literature by examining cross-informant ratings in emerging adulthood in adoptive families.