In "Principles to Actions: Ensuring Mathematical Success for All," NCTM (2014) defines productive struggle as students delving "more deeply into understanding the mathematical structure of problems and relationships among mathematical ideas, instead of simply seeking correct solutions" (p. 48). Hiebert and Grouws (2007, p. 387) state that struggle does not mean "needless frustration" or "overly difficult" problems but problems within a student's zone of proximal development, as defined by Vygotsky (1978). The zone of proximal development is seen as an educational target just beyond what a student can do independently when provided appropriate support. With this in mind, Cynthia Townsend wondered about the nature of her students' zone of productive struggle as she developed real-world mathematics tasks with the intent to encourage her students to dig deeper into algebraic relationships and experience productive struggle. At the same time, she also considered the proper nature and level of support she would need to provide. In this article, the authors describe two tasks they studied: (1) a set of problems related to human viruses, which introduced students to exponential functions. Students chose a virus to research, with a focus on its properties and reproduction number, created a table and graph, and answered open-ended questions about their findings; and (2) students chose a used car on the basis of their chosen career and their given salary. They then used tables, graphs, and equations to analyze the linear system related to the value of their car and the amount paid on their car loan. By applying Vygotsky's construct of the zone of proximal development to productive struggle, the teachers developed indicators to analyze students' zones of productive struggle. Students who were working within their zone of productive struggle were successful in completing and understanding the tasks with guidance from their teacher or peers and without continual frustration. Students who were working outside of their zone were overwhelmed, expressed negativity toward mathematics, and at times stopped working on the task. A bibliography is included.