With the rise of cloud and end-user computing, business units find it easier than ever before to craft their own IT systems and extensions to existing systems, often considered as “shadow systems”. However, shadow systems frequently disappear and organizations often fail to harness their innovative potentials. To explore reasons, we conducted a qualitative study with thirty-one experts from different roles and industries. From these interviews, we distilled twenty-six biographies of shadow systems and categorized the systems according to their size regarding scope of use and functional scope. We identified challenges occurring throughout their life cycles and we linked these challenges with the observation whether the system was still operational. Our empirical data supports the argument that smaller shadow systems are more likely to disappear by exemplifying several small shadow systems that were non-critical for an organization and that became discontinued when challenges with the system itself or in its context occurred. Furthermore, we observed that often multiple challenges co-occurred when a shadow system was discontinued. The results shed first light on typical patterns contributing to shadow systems’ discontinuance and scrutinize what it takes to nurture robust shadow systems.