Our goal is to improve the efficiency and effectiveness of natural language communication between humans and robots. Human language is frequently ambiguous, and a robot's limited sensing makes complete understanding of a statement even more difficult. To address these challenges, we describe an approach for enabling a robot to engage in clarifying dialog with a human partner, just as a human might do in a similar situation. Given an unconstrained command from a human operator, the robot asks one or more questions and receives natural language answers from the human. We apply an information-theoretic approach to choosing questions for the robot to ask. Specifically, we choose the type and subject of questions in order to maximize the reduction in Shannon entropy of the robot's mapping between language and entities in the world. Within the framework of the G 3 graphical model, we derive a method to estimate this entropy reduction, choose the optimal question to ask, and merge the information gained from the human operator's answer. We demonstrate that this improves the accuracy of command understanding over prior work while asking fewer questions as compared to baseline question-selection strategies.