Measurement is an important component of K-grade 12 mathematics curricula. The concepts of area and perimeter of polygons are first introduced in third grade and serve as the basis for teaching in the upper grades. Without a strong understanding of measurement, students will struggle to meaningfully grasp three-dimensional measurement concepts (e.g., volume) and will later make connections between area and more complex concepts, such as integration, which requires finding areas under curved surfaces. This article describes how elementary school teachers explored a task that encouraged them to consider area and perimeter simultaneously. Studies (e.g., Reinke 1997; Menon 1998) show that teachers, similarly to students, also struggle to develop robust understandings of measurement. So, although this task was implemented with teachers, the discussion offers insight into how upper elementary school students might approach this task and gives suggestions on effective ways to implement the task.