Recently, there has been significant expansion in the range of gambling activities supported by digital technology. The convergence of gambling and digital media is of particular concern with respect to the immense potential for earlier age of gambling involvement, and development of positive attitudes and/or behavioral intentions toward gambling. This study examined the prevalence of adolescent involvement in a range of digital and social media gambling activities, and the association between exposure to, and involvement in, simulated gambling and monetary gambling and indicators of pathological gambling risk. A total of 1287 adolescents aged 12-17 years were recruited from seven secondary schools in Adelaide, South Australia. The results indicated that a significant proportion of young people engage in a range of simulated gambling activities via internet gambling sites, social media, smartphone applications, and video-games. A logistic regression analysis showed that adolescents with a history of engagement in simulated gambling activities appear to be at greater risk of endorsing indicators of pathological gambling. These findings highlight the need for further research on the potential risks of early exposure to simulated gambling activities, as well as greater consideration of the need for regulation and monitoring of gambling activity via digital technologies.