Based on estimates from a large, nationally representative sample, persons with POUD were more likely than persons without POUD to engage in illegal behaviors at each time point from 2002–2014. In addition, persons with POUD became increasingly likely to sell illicit drugs, steal, have lifetime history of arrest, and to use heroin and other illicit drugs compared to their non-POUD counterparts over this time period. Results were substantively unchanged after adjusting for past-year non-heroin illicit drug use, suggesting that the increase in prevalence of illegal behaviors was specific to opioids. Further supporting the specificity to opioids was the lack of increased associations between other substance use disorders and illegal behaviors during this time period. Most of the associations between POUD and illegal behaviors appeared to be driven by heroin use; however, POUD was associated with an increased prevalence of selling drugs over time even after adjusting for past-year heroin use, suggesting observed increases in this illegal behavior was specific to misuse of prescription opioids. Finally, persons with POUD became significantly less likely to obtain prescription opioids for free from friends and family and significantly more to buy them from friends and family over time.