Research suggests that an offender–victim overlap within the physical and online environment exists. Therefore, it is unsurprising that online fraudsters have victimized each other (i.e., offender-victims) online. However, research is limited regarding the influence that the situational environment (e.g., online and cyberspace) has on online offender [fraudster] decision-making processes and their interactions with other online offenders. The current study uses criminological and communications theories to explore the influence of the situational environment on offenders’ interactions within illicit online marketplaces. A series of bivariate analyses were run to examine the relationship between the independent variables and the three dependent variables. Then, a series of negative binomial regression models were used to estimate the relationship between the dependent and independent variables. The findings suggest a positive correlation between messages from fraudsters and offender victims and emphasize the role individuals’ socially engineered (e.g., deceptive and manipulative) interactions impact targets, including offender victims.