Struggle and its connection to learning are central to improve student learning and understanding of mathematics. A description of what a student's productive struggle looks like in the setting of classrooms can provide insight into how teaching can support or hinder the student's learning process. In order for any struggle to be productive, these struggles with mathematics must be documented. However, prior studies on student struggles are limited and have primarily focused on examining whether or not struggle occurred. Thus, the purpose of this study is to describe pre-service middle grade teachers' (PSTs) struggle types in details as well as to investigate how engaging in a non-routine high level task (doing mathematics) fosters (or inhibits) productive struggle during instruction.