This article reports a study of coauthor Laura Wright as she learned to teach secondary school grammar in four settings: university teacher education program, student teaching, her first job, and second job. Data for her university program came from Laura's journals and projects from her course work. Data from student teaching and her first job included interviews and field notes from observations and interviews and self-reports by Laura of teaching conducted on other occasions. Information from her second job came from self-reports by Laura. The data were analyzed using a system that identified the pedagogical tools Laura employed and the attributions she made for learning how to use them. The data suggest that Laura sought to teach in ways that students found engaging, meaningful, enjoyable, and relevant. How she was able to make grammar instruction fit this goal varied according to the setting in which her instruction took place. (Contains 1 table.)