A weighted survey found that young people in NSW tend to commence simulated gambling and monetary gambling at much the same age (11-12 years). However, more young people engaged in simulated gambling and purchased loot boxes in the past year than engaged in traditional forms of gambling. All individual forms of simulated gambling were more popular than most forms of gambling, except for private betting. Reflecting a convergence of gambling and gaming, those who participated in simulated gambling were more likely to gamble. Problematic gaming was more prevalent than problem/at-risk gambling. Based on multivariate analyses, problematic gamers were more likely to participate in gambling but were not statistically significantly more likely to be problem/at-risk gamblers. Numerous personal, parental, peer and environmental factors were associated with gambling and gaming participation and problems. Parental factors were particularly influential, with parents being the greatest facilitators of youth gambling. Gambling with parents while growing up, parental approval of the young person’s gambling, growing up with an adult/s with a gambling problem, and not setting rules for online use predicted gambling participation, intentions and problems. Lack of parental rules for online use was also linked to simulated gambling participation and problematic gaming, but lower wellbeing and higher impulsiveness were stronger predictors.