This mixed methods study explored elementary students’ (N = 263) writing enjoyment, their perceptions of teacher writing enjoyment, self-regulation, and grades. In the quantitative strand, we examined how student perceptions of teacher writing enjoyment and student writing enjoyment relate to student writing self-regulation and writing grades using structural equation modeling. Findings revealed a positive relationship among student-perceived teacher writing enjoyment, student writing enjoyment, and student writing self-regulation and grades. In the qualitative strand, we explored responses of students with high or low writing enjoyment ratings to understand aspects of the instructional environment that contribute to students’ affective experiences with writing. Much of what determines students’ enjoyment of or aversion to writing fell in to one of two categories, regardless of the degree to which they enjoy writing: writing preferences (e.g., topic/genre selection, writing environment) or mood and motivation (e.g., student mood at the time of writing, self-efficacy for writing).