Andrés Segovia's repertoire—the repertorio segoviano—has crucially shaped the guitar canon. Although some guitar scholars argue that these works helped rescue the instrument from the periphery of art music, others contend that, by commissioning music from minor, conservative composers, Segovia missed the chance to request pieces from the most influential twentieth-century modernists. This article questions the conservative homogeneity of the repertorio segoviano. Focusing on Segovia's collaborations with Heitor Villa-Lobos, I argue that it contains traces of coloniality: The perpetuation of colonial domination in Latin America. The relationship between Segovia and Villa-Lobos was more contentious than the official narrative suggests—tensions stemming from their dominant personalities, divergent approaches to guitar composition, and conflicting musical ideologies. Indeed, although Segovia's stance aligned with Francoist and European conservative aesthetics, Villa-Lobos embraced a transcultural approach to music shaped by, a response to, and exertion of the coloniality of power—discrepancies that were engraved in their collaborations and ultimately the repertorio segoviano. This article ultimately foregrounds that elite composers from the periphery played an essential role in the modernization of the guitar in the twentieth century, thereby questioning historiographies that detach the instrument from the social, political, and cultural messiness of colonial difference and the coloniality of power.