In this article we discuss an open-ended problem involving quadrilaterals that we continually offer each semester. The task has been posed to undergraduate and graduate students in methods and problem solving classes. The task involves drawing all possible four sided figures with corners at the dots. A four by four array of dots is included in the instructions and students are asked to develop a system for knowing when they have identified all the quadrilaterals. Students are also encouraged to classify them in as many ways as they can and to look at the perimeters and angle measures. The focus of the discussion is on the potential richness of a task and how students engage in non-routine explorations. (Contains 6 figures.)