Inspired by my experiences while studying abroad in Colombia, in this paper I seek to explain the environmental, social, and political causes of widespread food insecurity in the Colombian department of La Guajira, a rural, isolated desert region with a high percentage of indigenous peoples. I first perform a literature review of geographic research on food security in peripheral regions, followed by a comprehensive case study analysis of La Guajira, drawing together sources from a variety of disciplines, in English and Spanish, in order to provide a new perspective on the region’s crisis through a multiscalar political ecology lens specifically focused on human-environment interactions, marginalization, social difference, and discourses. I find that from racialized frontier capitalism in the early 1900s to contemporary neoliberal extractivism, decades of attempts to integrate the region into national and global economic markets have weakened traditional food systems and substantially increased food insecurity. More broadly, I explore how food security, local agency in food systems, and environmental sustainability can be increased by rethinking our conventional ideas of “development,” “progress,” and “isolation.”