Children often refer to things ambiguously but learn not to from responding to clarification requests. We review and explore this learning process here. In Study 1, eighty-four 2- and 4-year-olds were tested for their ability to request stickers from either (a) a small array with one dissimilar distracter or (b) a large array containing similar distracters. When children made ambiguous requests, they received either general feedback or specific questions about which of two options they wanted. With training, children learned to produce more complex object descriptions and did so faster in the specific feedback condition. They also tended to provide more information when requesting stickers from large arrays. In Study 2, we varied only distracter similarity during training and then varied array size in a generalization test. Children found it harder to learn in this case. In the generalization test, 4-year-olds were more likely to provide information (a) when it was needed because distracters were similar to the target and (b) when the array size was greater (regardless of need for information). We discuss how clear cues to potential ambiguity are needed for children to learn to tailor their referring expression to context and how several cues of heuristic value (e.g., more distracters>say more) can promote the efficiency of communication while language is developing. Finally, we consider whether it would be worthwhile drawing on the human learning process when developing algorithms for the production of referring expressions. © 2012 Cognitive Science Society, Inc.