\chapter{Abstract} \thispagestyle{empty} The field of programming languages has recently experienced a renaissance, especially in the field of untyped scripting languages. But when scripts written in untyped languages grow into large programs, they may also become difficult to maintain. To improve the maintainability of programs in untyped languages, I propose porting portions into typed sister languages. To demonstrate the feasibility of this approach, I have developed Typed Scheme, a typed variant of PLT Scheme. Typed Scheme provides smooth and sound interoperability with untyped PLT Scheme; it also features a novel type system that supports idiomatic Scheme programming, so that the porting process is relatively straightforward. I have validated the effectiveness of Typed Scheme by porting thousands of lines of untyped PLT Scheme code. \cleardoublepage \vspace*{\fill} \vspace{-1.5in} \begin{center} \begin{quote} \textit{Why, anybody can have a brain. That's a very mediocre commodity. Every pusillanimous creature that crawls on the Earth or slinks through slimy seas has a brain. Back where I come from, we have universities, seats of great learning, where men go to become great thinkers. And when they come out, they think deep thoughts and with no more brains than you have. But they have one thing you haven't got: a diploma.} \hspace*{\fill} --- \textrm{The Wizard of Oz} \end{quote} \end{center} \vspace*{\fill} \chapter[Acknowledgments]{Acknowledgments\vspace{-24pt}} My original debt is to James D. Jungbauer Jr. and James E. Hamblin, who first taught me Scheme at the Johns Hopkins University Center for Talented Youth. But to the extent that I am more than merely someone who knows some Scheme, the credit is due to Matthias Felleisen, the advisor that I needed, and that made me the researcher that I am today. Matthias has been wise and impetuous, understanding and demanding, and has consistently expected and obtained better from me than I myself did. In between, I have been assisted by numerous people. Robby Findler and Laszlo Babai encouraged me to go to Northeastern. Once there, my colleagues have been wonderful resources: Dave Herman, Carl Eastlund, Felix Klock, Jesse Tov, Christos Dimoulas, David Van Horn, Aaron Turon, Dan Brown and many others have pushed me to make my ideas clearer and my thinking more precise. Ryan Culpepper, Stevie Strickland and Ivan Gazeau have been productive collaborators as well as fellow students. My colleagues at Sun Labs: Eric Allen, David Chase, Victor Luchancgo, Christine Flood, and Jan-Willem Maessen helped give me a wider perspective and fresh ideas. I have also been fortunate to work with Robby Findler and Matthew Flatt, both as co-authors and as co-developers. My committee, Mitch Wand, Olin Shivers and Guy Steele, have helped improve this dissertation. All my life, my parents have provided models of what it means to be an academic, and they have encouraged me at every step as I have pursued that life. One day I hope to live up to their example. Finally, my greatest debt is to my wife, Katie Edmonds, for which no thanks are enough.