Many teachers use problems set in real or imaginary contexts to make mathematics engaging, but these problems can also be used to anchor conceptual understanding. By constructing an understanding of mathematical ideas through solving problems in contexts that make sense to students, they have a better chance of actually understanding those abstract mathematical ideas (Lobato et al., 2010). Reasoning quantitatively goes beyond simply manipulating numbers; it means to think about what quantities in the problem situation those numbers refer to. In this article, the authors describe two ways teachers can press students to perform that sort of explicit quantitative reasoning, which emerged from videotaping and analyzing two teachers' practices (Reinke et al., 2023). The authors first distinguish between superficial and deeper enactment of the first way, pressing students to contextualize quantities. Then, they introduce the second way, pressing students to contextualize operations, which is a more challenging but essential form of support for students who need those grounding contexts to make sense of abstract mathematical ideas. After explaining both forms of press using examples from one teacher's classroom, the authors provide instructional suggestions for supporting students while engaging in this press, so that they can draw on the problem situations to make sense of the mathematical ideas.