We present results from a cross-sectional study of the entire adolescent student population aged 12-19 of the island of Kos and their parents, on the relationship between their Internet gambling and respective parental practices, including aspects of psychological bonding and online security measures. The sample consisted of 2,017 students (51.8% boys, 48.2% girls). Our results indicate that gender, parenting practices as perceived by the adolescents and distinct patterns of adolescent Internet activities are among the best predictor variables for Internet gambling. Security practices exercised by the parents failed to make an impact on the extent of Internet gambling, demonstrating the need for specific measures to tackle this phenomenon since the provision of simple education on the dangers of the Internet is not sufficient to this regard.