Research Findings: Parents' academic socialization of their young children is a critical yet understudied area, especially in the context of vulnerable parent-child dyads. The current longitudinal study examined factors that informed mothers' beliefs and practices concerning children's kindergarten readiness in a sample of 204 Mexican-origin adolescent mothers (M[subscript age] = 19.94). Adolescent mothers' individual characteristics and assets (i.e., parental self-efficacy, educational attainment, educational utility beliefs, knowledge of child development) and sources of stress (i.e., economic hardship, coparenting conflict) were related to the importance they placed on children's social emotional and academic readiness for kindergarten, their provision of cognitive stimulation and emotional support to their children in the home, and their enjoyment of literacy activities with their child. Moreover, adolescents' perceptions of parenting daily hassles emerged as a mediator in this process. Practice or Policy: Findings underscore the importance of considering Mexican-origin adolescent mothers' strengths and assets along with their unique contextual stressors as they relate to beliefs and practices that could have implications for their children's school success.