In this essay, I explore the impact of Panamanian secession and lost canal rights on Colombian domestic affairs. In particular, I focus on Bogota officials’ efforts to assert greater control over the nation’s only insular Caribbean territory: the archipelago of San Andres and Providencia. These islands are located less than one hundred miles away from the Canal Zone and their populations have a long history with coastal Panama. Through an examination of official correspondence, newspaper publications, travel accounts, and published memoirs; I put forth a two-part argument. First, I contend that the loss of Panama and rights to the canal forced central authorities in Bogota to reengage generally with their frontier populations—and more specifically, with the English-speaking Afro-Caribbean populations of San Andres and Providencia. Second, the historically loose commercial, cultural, and even kinship ties to mainland Colombia weakened central and local functionaries’ claims of territorial sovereignty to these islands, which in turn forced functionaries to compare island agitation, mobilization, and demands for political autonomy with the earlier efforts of nineteenth- and early twentieth-century Panamanians.