This paper initiates a discussion around the potential of Dynamic Measurement, an alternative approach to geometric measurement that focuses on how space is generated, and thus measured by the lower-dimensional objects that define it. I use data from a series of design experiments with fourth-grade students to illustrate some forms of reasoning about area and volume measurement that are possible when students engage with dynamic measurement tasks for generating rectangles, right prisms, and right cylinders. I argue that these forms of reasoning can be productive for students for developing a more conceptual understanding of area and volume measurement.