This paper focuses on family involvement in the education of teenagers at risk of dropping out from compulsory secondary school. A questionnaire was completed by 131 Spanish and Cypriot families with children at six schools – three in each country. The questionnaire investigated: (1) parental perceptions of their children’s activities in their free time; (2) academic expectations for their children; (3) parental concern regarding their children’s education; and (4) parent–teacher interactions. Descriptive measures and t-test comparative analyses between Spain and Cyprus were undertaken. Results show that these families have an encouraging attitude towards their teenagers. Nonetheless, significant statistical differences between Spanish and Cypriot parents suggest that the Spanish families have a more protective parenting style than the Cypriot families. The study points to the lack of support for these families as regards advice and stimulation for their children at home, and to the need to promote school–family partnerships.