In this chapter I present a personal account of three different assessment strategies through which I sought to address fundamental challenges in the assessment of undergraduate music theory at the Queensland Conservatorium Griffith University. This chapter briefly identifies the main contextual challenges and illustrates how each of the three assessment practices may enhance learning, provide contextualized experiential referents to musical techniques, and emphasize student-driven learning. The examples illustrate the development of music analysis portfolios that include works chosen by the students and incorporate student self- and peer evaluating processes. I reflect on the use of various assessment techniques to enhance, guide, and inspire the work that students do for their analysis portfolios. The chapter also illustrates an alternative use of a computer multiple-choice test format that focuses as much on drilling as on condensing concepts that are relevant for informing musical interpretation for performance.