This article considers the intriguing frequency of “proxy crossings” by British and American protagonists in international cultural advocacy that seeks to represent the West Bank checkpoint. This highly visible instance of the global checkpoint is the site of a spectacular confrontation between opposing notions of safety, embodied in the encounter between the Israeli soldier guarding the checkpoint and the Palestinian who seeks to pass through it. The narratives I am interested in prompt their readers or viewers to imagine themselves as the person requesting passage by placing a metropolitan protagonist at the checkpoint. Through this act of substitution, metropolitan audiences are asked not simply to side with Palestinians, but to share in their sense of fear and endangerment, and to recognize their common yet unequal implication in the global security order. At the same time, however, audiences are also reminded of the limits of this form of empathetic identification. When the intermediary figures in these narratives approach the checkpoint with fear and then cross it without incident, they are compelled to acknowledge their own safety, and in acknowledging that safety to feel shame, to feel ashamed that they are safe when others are not. The checkpoint thus becomes a site of political conversion, a site where the protagonist, standing in for the reader or viewer, can be persuaded to stand in solidarity with Palestinians.