With the global increase in demand for online tertiary education, teachers are facing unique challenges in scaling assessment activities and meaningful student engagement. One such aspect is contract cheating behaviours exhibited in the modern online environment — posing a threat to the academic integrity of tertiary education. These obstacles compound, when applied to traditionally difficult subjects like introductory programming education. Prior research on methods of identifying cases of contract cheating proposes that while challenging, techniques such as developing strong teacher-student relationships, and real-time discussions may lead to instances of identifying contract cheating behaviours. The proposition, then, is to scale real-time, student-teacher discussions with large, online cohorts — similar to those discussions which traditionally took place in the classroom. This poster paper presents Intelligent Discussion Comments (IDCs): A scalable, teacher-asynchronous system which engages students in real-time discussions to extract authentic student understanding. Artificial intelligence services such as voice identification and transcription enrich the discussion process, supporting the teaching team in their decision-making process.