The study of contract law is undergoing a difficult transition as it moves from the theoretical to the empirical. Over the past few decades scholars have focused largely on developing economic theories that offer a normative approach to setting the legal rules governing voluntary exchange. The time has now come to test whether these theories provide a meaningful basis for choosing our laws—in other words, to ask whether empirical data supports the theoretical models that contracts scholars have posited. Unfortunately, this type of empirical analysis has proven exceptionally difficult to conduct, and some commentators are beginning to question whether it will ever be possible to test and revise our economic theories of contract in a meaningful manner. Yet the problem of harnessing information to support complex decisions is not unique to contract law. This Essay explores the possibility that recent technological developments from the field of organizational knowledge management—including advances in meaning-based computing algorithms—will soon make it easier to conduct empirical work in contract law on a much larger scale.