This chapter provides a single person case study of Mr. Dan DeFilippi who was arrested for credit card fraud by the US Secret Service in December 2004. The chapter delves into the psychology of a cybercriminal and the inner workings of credit card fraud. A background context of credit card fraud is presented to frame the primary interview. A section on the identification of issues and controversies with respect to carding is then given. Finally, recommendations are made by the convicted cybercriminal turned key informant on how to decrease the rising incidence of cybercrime. A major finding is that credit card fraud is all too easy to enact and merchants need to conduct better staff training to catch fraudsters early. With increases in global online purchasing, international carding networks are proliferating, making it difficult for law enforcement agencies to be “policing” unauthorized transactions. Big data may well have a role to play in analyzing behaviors that expose cybercrime.