This paper navigates the complex interplay between cultural tradition and controversy through an in-depth exploration of Penitensya, a Filipino Lenten ritual known for its violent self-mortification practices. By employing indigenous research methods, we investigate the motivations behind participants' involvement in Penitensya, framing this event as a distinctive form of religious-dark tourism. While the ritual remains a resilient practice despite the Catholic Church's disapproval, its promotion as a tourist attraction raises critical questions about cultural representation, tastefulness, and visitor safety. Our analysis reveals that Penitensya attracts participants and spectators alike, driven by a desire for unconventional cultural experiences and voyeuristic intrigue. However, promoting Penitensya within the context of cultural tourism risks reinforcing harmful stereotypes that portray Filipinos as barbaric for engaging in these acts. This research highlights the delicate balance between preserving dark events as examples of cultural heritage, and managing visitor, as well as global perceptions. We argue that Penitensya holds potential as a legitimate facet of Filipino intangible cultural heritage, but this recognition requires careful navigation of the contentious issues surrounding its representation and commercialization. In advancing our understanding of Penitensya, we underscore the need for strategies that respect its cultural significance while preventing misinterpretation and misrepresentation.