The findings of this inquiry emerged from a research study conducted over two years in two schools investigating how teachers support learners from populations who have been historically underserved by a provincial education system in Canada. Emerging from a focus on how teachers in four rural middle school classrooms supported literacy acquisition through teaching in the content areas, this work revealed asset-based pedagogies made visible by teaching and learning routines that provided learners supportive spaces to grow. Each of these routines was developed by teacher participants to enable students to think, ask questions, make choices, assess their learning, and take risks as learners. The results of this study affirm what is known about how to support learners in culturally and economically diverse classroom contexts and afford new understanding about asset-based informed learning routines that can encourage students to take risks academically. As learning routines have not often been studied in relation to culturally relevant pedagogy, culturally sustaining pedagogy, or additive schooling theories, this study suggests a novel intersection with these asset-based pedagogies. This intersection offers fresh possibilities for understanding their enactment in classrooms.