How do curatorial initiatives in public spaces balance the critical pursuit of art and the professional ethics of the exhibition context? What are the pros and cons of conducting attention-grabbing guerrilla campaigns versus infiltrating politically sensitive public arenas with long-term initiatives? What happens when corporate sponsors of art become trapped in the battlefield of art-fueled media controversy? This article expands on such inquiries by analyzing the collision of two artistic urban interventions, Open Sky Project and the Countdown Machine campaign—a collision that took place within the delicate political context of Hong Kong in 2016.