Contract cheating is becoming a real challenge to many universities. Not only is it a relatively new phenomenon, but also it is difficult to prove as the work is often original and unlikely to be detected using standard anti-plagiarism text-matching services such as Turnitin or Erkund. Using a literature review approach, this chapter examines why students in general would take risks to engage in contract cheating and what strategies could be implemented to prevent or lower the chance for them to be engaged in this type of academic misconduct. An Australian regional university, which is also a leader in distance learning in the country, was used as a case for this study. The findings and recommendations provide insights for Australian university policy-makers when developing strategies, procedures and policies to face this issue. Limitations and future research directions are also discussed.