Over the last few years, the protective role of parental monitoring on adolescent adjustment (i.e., active parental efforts aimed at setting limits and tracking adolescents’ activities and whereabouts) has been challenged. Recent research has shifted attention to the conditions under which monitoring may be more or less effective. Grounded in Self-Determination Theory, this study investigated the role of parents’ autonomy-supportive and psychologically controlling parenting in effects of parental monitoring on adolescents’ adjustment. It also considered the role of adolescents’ clinical status (i.e., clinically referred vs non-referred). Adopting a person-centered approach, we aimed to identify naturally occurring profiles of monitoring, autonomy-support, and psychological control and to examine differences between these profiles in terms of life satisfaction, positive affect, and internalizing and externalizing problems. Participants included 218 referred (Mage = 14.44, 56% girls) and 218 matched adolescents from a larger sample of 1056 community (Mage = 14.83, 52.9% girls). Multigroup Latent Profile Analyses revealed five parenting profiles which were structurally equivalent in both samples: high monitoring with either high autonomy support or high psychological control, low monitoring with either high autonomy-support or high psychological control, and an average profile. Referred youth were significantly more present in the average profile and in the profiles characterized by high levels of psychological control. As hypothesized, profiles showed a differential association with adolescents’ self-reported adjustment, with the high monitoring—high autonomy support profile yielding the most optimal and the low monitoring—high psychological control profile yielding the worst outcomes. Associations between profiles and outcomes were similar for referred and non-referred adolescents. These findings highlight the importance of considering the parenting climate (i.e., autonomy-supportive versus psychologically controlling) to understand effects of parental monitoring during adolescence.