Adolescents’ use of the Internet and other digital media for the purpose of gambling represents a serious concern in modern society. This paper overviews some of the available monetary and non-monetary forms of gambling within new digital and online media and monetary forms of games with gambling-like experiences. With reference to current psychological knowledge on the risk factors that promote adolescent gambling, it is suggested that new gambling technologies may: (a) make gambling more accessible and attractive to young people, (b) may promote factually incorrect information about gambling, (c) provide an easy escape from real world problems such as depression and social isolation, (d) create a gambling environment that easily facilitates peer pressures to gamble, (e) ease parental transmission of gambling attitudes and beliefs, and (f) make gambling more ubiquitous and socially acceptable. The unique risks of Internet gambling for young people are critically discussed, as well as the lack of restricted classification for video games and other media that feature interactive, non-monetary forms of gambling.