Although the association between parenting stress and child behavioral outcomes is well established, there is limited research with families of adolescents. Due to multiple transitions occurring and adolescents seeking independence, this developmental period may be especially difficult for families compared to earlier stages of child development. Exploring the influence of parenting stress on adolescent externalizing problems and how parenting can explain this link can inform parenting of adolescents, reduce the risk of adolescent deviant behaviors, and promote a smoother transition into adulthood. Thus, this study examined associations between parenting stress and externalizing problems (i.e., oppositional behaviors, proactive aggression, and reactive aggression), considering whether parenting behaviors (i.e., acceptance, psychological control, and lax control) served as mediators among 282 biological mothers (ages 28–61; M = 40.29; SD = 6.6) with 12- to 17-year-old adolescents (M = 14.19; SD = 1.84; 50.7% males). As expected, parenting stress was positively associated with all forms of adolescent externalizing problems. Additionally, parental acceptance mediated the association between parenting stress and all adolescent outcomes. Psychological control only mediated the association between parenting stress and oppositional behaviors and reactive aggression. Lax control only mediated the link between parenting stress and proactive aggression. The findings suggest that examining parenting dimensions and adolescent externalizing problems separately provided specificity that can inform future research and clinical interventions. Clinicians may benefit from assessing for and treating parenting stress among families with adolescents and targeting increasing parental acceptance and decreasing parental lax and psychological control during parenting interventions.