In response to recent trends in the field of mathematics education, real-world contexts are frequently found in curricula and classrooms across the world. Numerous scholars contend that, in addition to making instruction more engaging and relevant, rich, imaginable contexts can provide a semantic grounding that helps students deeply understand abstract mathematical ideas. To achieve this form of understanding, A. Thompson et al. (1994) describe the need for conceptually oriented teaching, aimed at supporting students in maintaining connection between numerical values and operations and the quantities and relationships to which they refer. We elaborate the construct of conceptually oriented teaching through an empirical analysis of two teachers' instruction around a context-based ratio instructional sequence. More specifically, we differentiate between two types of explicit contextualization present within conceptually oriented explanations: contextualized quantities and contextualized operating. We identify the importance of a particular teacher move, "pressing for contextualized operating," that aims to explicitly ground students' use of representations to their common sense understanding of the problem context. We describe two ways that the teachers work to make the contextualization explicit in the classroom discourse and argue that this explicit contextualization is essential in order for all students to have the opportunity to experience the contexts as supportive of conceptual development.