Teachers readily welcome instructional materials that situate mathematics in the real world because they provide the relevance of mathematics to students who genuinely seek the answer to the question, "When are we ever going to use math in real life?" Although using the real world as a motivational hook is often effective for engagement, a number of scholars point to a more conceptual purpose as well: the potential of the real world to support students in making sense of abstract mathematical ideas by connecting to their existing knowledge of the world around them (e.g., Freudenthal 1991; Lesh and Lehrer 2003). It is this point that the authors wish to explore in this article, that real-world contexts can play an expanded, conceptual role in mathematics learning. The authors contend that certain contexts can serve not only as hooks but also as anchors that ground students' reasoning in contextual experiences and continue to support the transition to abstract reasoning. The authors use the work of several middle school teachers who use realistic contexts as both hooks and anchors to illuminate three characteristics of real-world contexts: (1) to support the transition from concrete to abstract reasoning; (2) to engage students in conceptual mathematical discourse; and (3) to capitalize on real-world and experientially real-world situations.