A variety of research and technologies for programming education, in particular, and design, in general, has been produced by the laboratories of Elliot Soloway during the past decade: the Highly Interactive Computing Environments (HiCE) Group at the University of Michigan, Ann Arbor (1988 — present); and, the Cognition and Programming Project (CAPP) at Yale University (1981 – 1988). Central to the work produced by HiCE and CAPP have been discussions with and about students. Some of our efforts have gone into describing or modelling students. Some of our efforts have gone into getting students to describe themselves. These descriptions have been videotaped, catalogued, refined into computational cognitive model, transformed into academic papers on computers and education and been used, implicitly and explicitly, to build educational computer systems. Over the last ten years our models of students have moved away from mainstream artificial intelligence, objectivist formulations towards a more community-responsive, constructivist understanding of students. Starting with two issues that motivated many years of student modelling work -- "bugs' and "transfer" -- we tell our story of how, as our work with computers in the classroom has changed, our theories about student knowledge and learning have been forced to change and so, reflectively, has our understanding of "bugs", "transfer", and student models changed. Central to our story are philosophical discussions detailing our shift in position from objectivist to constructivist.