Certified organic and Fair Trade food products are making their way into the mainstream among Western consumers and, as such, are increasingly viewed as sustainable and preferable alternatives to the conventional food system, with its many negative social and environmental externalities. Two case studies discussed in this paper indicate, however, that operationalizing the goals for organic and Fair Trade food via certification can be a complex and difficult process. Specifically, the implementation of certification creates a disconnect between expectations raised by labels and the ‘lived experience’ of small farmers. In the case of small farmers in Mexico growing certified organic tomatoes and herbs, certification exacerbated socio-economic inequality and disrupted local social norms by creating a hyperfocus on surveillance. In the case of small farmers in the Dominican Republic growing Fair Trade bananas, the certification process prioritized the demands of the market to such a degree that the farmers were largely unaware that they were participating in anything ‘alternative’, and it simultaneously reinforced socio-economic inequalities within the communities. These findings suggest that if the appeal of certified labels rests on the integrity of what the label represents to consumers, then such consumer movements would benefit from a more robust analysis of how certification intersects with and affects local spaces, cultures and communities at the point of production.