This paper uses a case study of Jamaica to examine the importance of parental involvement in children’s education as a way of improving education and child outcomes as well as of stemming the transmission of conditions of poverty and exclusion across generations. The paper argues that while the involvement of parents is widely acknowledged as critical to the education process, there are systemic and societal barriers which impinge on parents’ exercise of agency in their children’s upbringing. Given prevailing power relations in the Jamaican society, parents are often not given adequate social space in the context of their child’s school and are sometimes made to feel as if they have little to contribute to the education process because of their own low levels of educational attainment. This leaves some parents feeling powerless. Furthermore, given the inherently closed and elitist bent of education—particularly secondary education— in Jamaica, parents can feel alienated by the education system. This sense of alienation and powerlessness affects the way in which they fulfill their parenting role, generally, and how they involve themselves in schools and education in particular.