As supported by ecological systems theory and the family stress model of economic hardship, socioeconomic status can directly be related to adolescent adjustment outcomes including self-regulation, academic performance, and substance use as well as be indirectly related to these outcomes through the mediator of parental monitoring. Data obtained from 220 adolescent (male = 55%, female = 45%, mean age = 15.12 years) and primary caregiver dyads participated in the study to examine the relationship between these variables. Analyses were conducted using Structural Equation Modeling, and the results of the study demonstrate that economic hardship is directly related to adolescent academic performance and also indirectly related to this outcome through maternal monitoring. Parental monitoring was also positively related to adolescent self-regulation. Therefore, this study highlights the importance of high levels of parental monitoring for beneficial adolescent self-regulation, academic, and substance use outcomes.