Engaging in productive struggle--grappling with challenging problems--is conducive to understanding mathematics. This paper examines five pre-service teachers as they learned to engage English language learners in productive struggle. The context of this descriptive case study was an elementary mathematics methods course in the Northeastern United States. Data collected included surveys, interviews, lesson plan reflections, and homework reflections. After selective coding, data were analyzed individually before using cross-case analysis. A possible trajectory to productive struggle is presented. The trajectory requires refinement, but it offers teacher educators insight for teaching pre-service teachers to engage all students in productive struggle.