There is a large body of research that indicates the practice of cheating amongst students in the tertiary sector is widespread. Various studies have also attempted to determine reasons why students decide to cheat, or not to cheat. Although some common factors have been identified, there are indications that the level of cheating varies across disciplines of study, suggesting that there may be factors in specific learning situations that have influence on a student’s propensity to cheat. This paper reports on two studies, one which investigates the cheating practices of IT students and their attitudes toward cheating, and the other which investigates the work practices of IT students. These studies identify particular problems that IT students face in their learning and give insights into situations which can lead to poor learning practices and, in the worst cases, cheating.