While there is growing literature regarding the impact of the gig economy in countries of the Global North, the way it operates in Latin America and the Caribbean remains underexplored. This article describes platform work in Chile, especially in the context of COVID-19, which has highlighted the essential role of geographically tethered digital platforms in facilitating essential goods and services in times of social distancing and quarantine. While the gig economy has provided employment for those outside traditional labor markets, its supposedly ‘collaborative’ employment structures obscure the different costs of precarity and informality transferred from platforms to workers (Ravenelle, 2019). Based on 35 interviews with gig workers using the Fairwork framework to evaluate working conditions in the gig economy, this article examines digital labor relations, both on paper and in reality; the conditions and limitations gig workers face daily; and their perceptions regarding such platforms. We discuss the contradictory experiences felt by platform workers, dependent on the platform in some ways, and independent in others. We argue that the inherently contradictory conditions and circumstances of platform work have become even more salient for gig workers in the context of COVID-19: risks increasingly fall on workers as platforms continue to stress their ‘choice’ to do so. This article reveals that the nature of the linkage between platform and worker is eminently a labor relationship, with clearly established elements of worker dependence.