This paper presents the results of an exploratory study that examined engagement approaches of contract cheating services on the Twitter platform. The literature portrays the grey academic market as an invisible hand that magically delivers academic content at the click of a button, which leaves a wide gap in our understanding of their outreach efforts. To this end, data from 71 contractors and 12,701 users were analysed to describe what academics and administrators are up against. The results suggest that contractors employ automation tools to generate leads, specific to their subject area, which denotes market segmentation and competition. This study is part of a larger project aimed at minimizing academic misconduct; it discusses implications for educational practice and offers recommendations for prevention of contract cheating.