The potential of digital storytelling in cultural heritage has been widely recognized as an effective technique for communicating heritage interpretation to the public. In this paper, we explore its application in a "dark heritage" setting—a cultural heritage site associated with death, atrocity and human depravity. Although literature within the field of dark heritage emphasizes a fascination with death as the main (if not sole) motive for visiting, according to some studies and the visitor study we performed in the context of our work, motives are in fact varied, and include a desire to learn and understand the history presented and an interest in having an emotional heritage experience. Borrowing from education, we use the notion of "essential questions" as a tool to lead to a deeper understanding of human nature. Following a user-centered design methodology, we develop an interactive digital storytelling experience for the Criminology Museum of the University of Athens. The resulting experience is adapted so as to be tested on-site and through the web. We conclude the work with our insight on guidelines for sites with similar characteristics as well as addressing open issues and challenges for the application of digital storytelling in dark-heritage contexts.