Social learning is widespread but the causes for variation in the use of social versus private information are not always clear. Alongside adaptive explanations, suggesting that animals learn socially only when it is indeed adaptive to do so, it is also possible that the use of social learning is limited by mechanistic constraints. A common, but frequently overlooked challenge for social learning mechanisms is the need to allow learners to solve a problem through watching it being solved by others. This requires animals to be able to shift between contexts: from the context of the observed solution, to the context of the unsolved problem. For instance, for the social learning of cues associated with hidden food, an individual that merely sees a conspecific exploiting the food must, in the later absence of demonstrators or visible rewards, also learn to explore the cue for itself. Here we show that this shift in context can indeed be difficult. In two experiments involving sand colors, house sparrows trained with hidden seeds learned to search for hidden seeds (based on food-color association) better than sparrows trained with exposed seeds. However, the latter showed color preference when tested with seeds exposed on both sand colors. These results demonstrate that context-specific learning makes it difficult to generalize reward-cue association from “exposed” to “hidden” conditions, which may explain why social learning is often more effective when it is based on socially facilitated active search (for hidden food), similar to that used in the context of independent foraging.