Recent developments in routine activities theory have sought to conceptualize the notion of capable guardianship, as well as to broaden the application of the theory to the corporate crime context. Building on this work with systematically collected qualitative data, we examine the mechanisms in which offenders commit corporate financial fraud and identify the failures in guardianship. In addition to the unique dimensions of corporate crime already identified (i.e., specialized access to targets), our work highlights the need to consider guardian–offender overlap, or instances in which those tasked with guardianship responsibilities become motivated offenders. Our findings suggest financial regulations focusing on adding layers of guardians may be insufficient. They also have broader implications for understanding guardian capability in other forms of crime—namely, the need to consider the costs and benefits of intervention, willingness and ability to intervene in differing contexts, and how these dimensions of guardianship shape offender risk perceptions.