Italy invaded Ottoman Tripolitania, Fezzan, and Cyrenaica (today’s Libya) in the fall of 1911, initiating a brutal conquest that was met by about two decades of armed resistance. In neighboring Tunisia, outrage at this invasion merged with ongoing tensions with Italian settlers, who far outnumbered the French despite the country having been occupied by France since 1881. This paper explores how cultural and economic links between Tunisians and Tripolitanians were mobilized in response to Italian colonial aggression, catalyzing an unusual blend of political formations that crossed colonial boundaries. Among Tunisian intellectuals, renewed affinities with the Ottomans and the Arab Mashriq blended with a liberal reformism that began to challenge French rule and imagined a greater Maghribi state under Ottoman sovereignty. In Tripolitania, religious-political leaders such as Sulayman al-Baruni and Ahmed Sharif as-Senussi fostered pan-Islamic ideologies that envisioned a similar pan-Islamic future for the region. The little extant literature on this conflict has focused on these elite political currents, which themselves deserve further study. But going even further, this paper presents new research into what Tunisia-Tripolitania links looked like on the ground through the eyes of locals on both sides of the border, including smugglers, soldiers, and medical workers. To do so, I use the recently catalogued personal archives of Tunisian photojournalist Albert Samama-Chikly (1872-1934), providing access to the usually obscured perspective of the more rural and mobile populations along this frontier. Samama was one of the few reporters to document this conflict from behind Ottoman lines, at a time when the European media was mostly inclined to support what they saw as Libya’s liberation from Ottoman tyranny. But the French-educated Samama, born to a Jewish father and Italian mother, was also a confounding figure to the locals he met along the way. At times he won their trust, leading to passionate discussion of political affairs; at other times, he provoked accusations of espionage for imperial powers. Using Samama’s personal diaries and relevant articles from the popular press, this paper situates the political sympathies of locals along the Tunisia-Tripolitania frontier within the broader politics of Arab-Muslim reformism and imperial competition in the central Mediterranean.