Detecting contract cheating in written submissions can be difficult beyond direct plagiarism detectable via technology. Successfully identifying potential cases of contract cheating in written work such as essays and reports is largely dependent on the experience of assessors and knowledge of student. It is further dependent on their familiarity with the patterns and clues evident in sections of body text and reference materials to identify irregularities. Consequently, some knowledge of what the patterns and clues look like is required. This paper documents how to identify some of the patterns and clues observed in essay and report submissions. Effective assessment design with specific contextual requirements make irregularities easier to detect and interpret. The irregularities identified were confirmed as instances of contract cheating through conversations held with postgraduate students. An essential element of the conversations was the evidence presented for discussion. Irregularities were noted on a pro-forma specifically developed for this purpose. Patterns identified include misrepresented bibliographic data, inappropriate references, irrelevant material and generalised text that did not address the assessment question or grading criteria. The validated patterns formed the basis of identifying potential instances of contract cheating in later submissions. Timely conversations with students before the end of semester are essential to determining whether the patterns and clues link to poor knowledge of academic writing conventions or classified as contract cheating necessitating the application of appropriate penalties under institutional policies and procedures.