In recent years, many adult returning students go back to school for college degree and retooling. Many of them are struggling with computer literacy skills. In this study, we try to understand the computer related challenges that adult returning students are facing. We identify the difficulties they encounter through direct observations in classroom. We also use informal conversations with students to help us understand why they have the challenges. Next, we conduct critical analysis by taking the conceptual lens of empathetic thinking and disruptive information technology (IT) innovation. We discover several factors that may contribute to adult returning students’ struggles with computer literacy. Furthermore, we suggest several ways that may help adult returning students overcome the adversity. This research will contribute to our general understanding of the computer literacy challenges faced by adult returning students. The research findings also have important implications for Information Systems (IS) educators and college administrators.