In this article I respond to a call for inquiry into the teaching process using one's own teaching as the object of inquiry. A focus on the dilemmas faced by an individual teacher acknowledges that teaching is, as Wineburg (1991) put it 'a complex activity fraught with pitfalls, problems, setbacks, failures, errors and disappointments' (p.278). Single cases have value if they contain elements that can be generalized beyond the specific personalities and contexts of the given situation. In this article I describe the evolution of a portfolio-based assessment course in a traditional teacher education program. I describe the elements of the course, the aims of instruction, and the potential power of portfolios and authentic performances to enhance student learning. I also describe the problems that may arise from the use of portfolio and performance-based assessments. The various adjustments made during a 3-year period to make the course workable for both students and the instructor are described as an evolutionary process. The problems and their solutions can be generalized beyond the given assessment course and show the kinds of decisions teachers must make for their students and for themselves when using portfolios in teaching.