This article focuses on the development and problematization of a task designed to foster spatial visual sense in prospective and practicing elementary and middle school teachers. We describe and analyse the cyclical stages of developing, testing, and modifying several "task drafts" related to ideas around dilation and proportion. Challenged by participant non-actions and non-responses, we as task designers identified and anticipated sources of difficulties, which motivated repeated modification of the task to further the intended learning goals. The task in its present form incorporates numerous considerations including choices around materials, wording of questions and prompts, and sequencing of experiences. It also reflects our enriched understanding of exploration strategies and the roles of manipulatives and technology in spatial visual tasks designed for adult learners.