The Adventures of Jasper Woodbury is a technology-integrated program developed by Vanderbilt University which attempts to provide rich contexts for mathematical thinking and problem solving about real-world situations. This article gives specific examples from the Series, as well as describing promising extensions being planned. Although most of the reported benefits gotten through the use of the series comes from people using it directly under the tutelage of Vanderbilt, it is exciting to know of mathematics programs that approach the goals laid out by the NCTM standards.