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Increasing attention to sustainability experiments is being paid by transitions researchers. The use of a range of definitions, however, leaves the field rather underdeveloped and disorganized. This paper will first provide an overview of the origins of interest in experiments, and their theorized functions, within the major transition perspectives. The overview points to a dilemma in transitions research: transitions are thought to be managed and therefore top-down processes but innovation and change are theorized to come from the bottom up. Next we review various types of sustainability experiments and their definitions. In the interest of resolving the dilemma, we propose a definition of sustainability experiments that maintains enough breadth to capture a wide range of possible experiments while at the same asserting some conceptual order on the scattered uses of sustainability experiments in transitions research. Our definition gives rise to a “middle-out” approach where learning from innovation that occurs outside the context of traditional experimental definitions and designs (i.e., in a bottom-up and unplanned manner that may lack the network links of experiments implemented within more formal structures) can nevertheless take place and inform top-down actors. Future research could examine how a hybridized bottom-up/top-down knowledge system can shape or trigger transition dynamics at various levels.