This qualitative, classroom-based study investigates how 24 middle school students engaged with grammar in an instructional approach that bridged “grammar in context” practices with writing transfer practices. This “transfer-minded” approach invited students to monitor and reflect on their grammar choices in writing as a way to foster metacognition; it also guided students to consider other and future writing contexts where they could use the grammar they were learning as a way to foster transfer and long-term writing development. The dissertation findings detail the role of individual factors on student engagement with grammar in this study. The findings also share how students thought about and used grammar in their writing. Finally, the dissertation reveals how students engaged with the instructional practices, helping map successful and promising areas for effective grammar instruction.