Corruption is an age-old issue. Although various mitigation measures have been developed over time, it persistently exists and transforms with the dynamic business environment. The development of corruption is linked to the skills of criminals to cover their tracks. Control mechanisms and other lines of defense are insignificant when persons of power override, bully or collaborate to carry out corruption. Since humans are perceived to be rational, educating individuals on the evils of corruption with its apparent negative connotations would have been a logical approach to disrupting corruption. However, the growing trend of corruption reflects otherwise. Human behavior is subjective and based on a person–situation complexity, relationships and associations around human life. This pilot study assesses the decisions of individuals based on various corruption scenarios, using 20 questions modeled around Corruption Dimensions and Prisoner’s Dilemma. Of the respondents, 92% had formal exposure to anti-corruption-related studies. Most respondents responded negatively to corruption-related scenarios in the Corruption Dimensions, with noted bias in their criticism when it involved a politician as compared with a businessman. Similarly, the Prisoner’s Dilemma questions also reflected selective reasoning when comparing those with personal relationships as compared with acquaintances. The strength of the evidence, the independence of the judiciary, the ability to escape, the reluctance to self-incriminate and the personal benefits affect the judgment of the respondents. However, in situations involving environmental issues, respondents selected to confess regardless of the situation stating that it was the right thing to do. Education creates awareness on individual rights, options and, to a certain extent, the moral and legal obligations. However, the subjectivity of the person’s associations and lifelong experience also plays a major role in the decision-making process.