Philosophies of assessment are rare, perhaps even more so in music education. This chapter, arranged in five “movements” intended to reflect various ways of examining assessment issues, considers prominent themes emerging from the music education assessment literature, such as accountability, authentic assessment, consequential validity, legitimacy, mandated testing, metaphor, power-knowledge, and self-determination. The author asks questions such as, To what extent should philosophical commitments be voluntary versus compelled? To what extent should music educators be able to collectively determine educative values and to what extent should others (policymakers, local communities) have a say in what should constitute valuable learning in music? A common theme throughout the chapter is the urge for caution and reflection so that well-intended assessment efforts do not undermine cherished goals for music education.