Simulated gambling products contain gambling elements, but they are not classified as gambling and are legally available to underage people. There are concerns about a "gateway effect" from simulated gambling to monetary gambling. This study examined the time course of young people’s engagement in simulated and monetary gambling. It also looked at the associations between simulated gambling and gambling problems and harms. The use of loot boxes and video games with gambling content tended to come before monetary gambling. Engaging in simulated gambling products in which gambling is a core element (e.g., social casino games) tended to occur after monetary gambling. Most simulated gambling products were associated with greater harm from monetary gambling.