A growing body of evidence suggests the situational context influences the social engineer (SE) characteristics and tactics offenders (i.e., fraudsters) deploy during the development of an online fraud event. Several attempts have been made to examine online the macro-social development of an online fraud event. Nevertheless, macro-level social examinations have been largely unsuccessful in combating online fraud because offenders and victims, including offender victims, are not computers; therefore, offenders’ interactions, motives, and tactics are very difficult to surmise. To address online fraud, three independent studies were conducted to explore what is known about online fraudsters and investigate what is not accounted. Specifically, a scoping review of offenders SE characteristics and tactics is conducted. In addition, two empirical investigations examining linguistic cues used by offender and offender victims are conducted. for that present day literature or governmental reports do not address. Together, these studies examine the influence of the situational context on offenders’ decision-making process, like their SE characteristics and tactics. The results and limitations associated with each study, along with recommendations for further research are discussed.