The emergence of the National Association for Music Education (NAfME) Popular Music Special Interest Group, "Journal of Popular Music Education," and Association for Popular Music Education among articles, books, presentations, stories of educators engaging students with popular music, and this special issue demonstrate that music educators are addressing popular music and thinking deeply about music learning and teaching. The author observes a shift moving from "should we address" popular music to "how do we address" popular music, then from how to address popular music from a technical perspective to how to enact practices that "account for sociocultural issues," such as equity or cultural appropriation. In the spirit of inquiry, this article reflects on context in relation to popular music, music programs, and curricular structures.