Objective: Student mental health may suffer due to unreasonable expectations associated with academic entitlement; permissive parenting may be one source of these expectations. The authors examined the role of academic entitlement as a mediator of the relationship between permissive parenting and psychological functioning. Participants: Participants were 524 undergraduate students at a single institution (52% female; age range = 18–22). Data collection was completed in May 2011. Methods: Cross-sectional design. Participants completed online self-report measures of parenting styles, academic entitlement, stress, depressive symptoms, and well-being. Results: Permissive parenting was associated with greater academic entitlement and, in turn, to more perceived stress and poorer mental health. Mother/father differences were found in some cases. Conclusions: Academic entitlement may partially explain why permissive parenting is detrimentally related to mental health for college students. Implications for academic affairs and counseling include helping students develop an appreciation of the role of self-regulation in college success.