My research investigates emerging and contested forms of street-vending in Cuba. Recent work in the anthropology of labor has interrogated how capitalist relations shape labor practices heterogeneously across the globe, responding to local histories. Emergent changes in Cuba challenge these formulations through an economy that does not self-identify as capitalist, and one that is undergoing drastic transformations after nearly six decades of socialism. In 2010, president Raúl Castro announced the need to "update and improve" Cuban socialism by legalizing forms of self-employment repudiated after the 1959 Revolution, causing an unprecedented resurgence of street vendors and their songs in Cuban streets. While scholars have recognized the importance of street vendor songs in the development of Caribbean popular music genres, no work has focused on the nuanced ways street vendors and their song are tied to labor reform that is changing everyday life in Cuba in a present context of general scarcity. Beyond their musical significance, street-vendor calls force us to reconsider how their attendant modes of listening foster new forms of social relations with respect to labor, infrastructure, and morality in a context where the Cuban Revolution's prior paradigm of the "New Man" is shifting from valuing moral rewards to assessing risk and material gain. How do vendors and buyers negotiate living under precarious conditions while creating new modes of exchange and transacting as they contest and construct livelihoods in contemporary Cuba? Through participant observation, apprenticeship, and archival work, I focus on three aspects of street-vending in relation to labor and infrastructure: (1) vending practices; (2) consumption practices; and (3) the relationship between vendors, consumers, and the state.