This paper is situated in French-occupied southern Tunisia during World War I. It takes the ambiguous perspective of the Jewish Tunisian photographer Albert Samama-Chikly, who served with the French Army’s Section Photographique de l’Armée (SPA) during the war. In early 1916, before his longer stints at the Western Front, Samama was sent to southern Tunisia, close to his home country’s border with Tripolitania (part of Italian Libya). There he captured the blurry lines between French conscription centers and the prison camps built alongside them to house dissidents and deserters. Expanding wartime conscription measures were in part to blame for the rebellions. But Samama, having traveled in the region as a photojournalist just a few years earlier during Italy’s 1911-12 invasion of Ottoman Tripolitania, was positioned to understand that many of the rebels came from the very communities and tribal confederations who straddled the Tunisia-Libya border. Now, in 1916, their ongoing resistance to Italian rule had begun to merge with anti-colonial sentiments in French-occupied Tunisia. This paper therefore uses photographs, military and colonial documents, and personal documents to weave together two interrelated layers of the colonial experience in North Africa: 1) the complicated position of elites such as Albert Samama-Chikly, caught between the suffering of fellow North Africans and the Francophone upbringing that had landed him a coveted position in the French Army; and 2) the transnational origins of anti-colonial movements in and around Tunisia, long obscured by nationalist narratives but now revealed by the unique lens of Samama. The first, an intimate microhistory, offers a means of understanding the second, a transnational phenomenon not always visible to states, empires, or their histories.