Implementing mathematically challenging tasks is difficult for teachers when working with emergent bilinguals because cognitively demanding tasks in mathematics commonly have high language demand. Currently, inadequate teacher preparation for teaching emergent bilinguals is becoming a significant concern in the United States as this population of students is rapidly growing. This study investigated how two mathematics preservice teachers (PSTs) support middle school emergent bilinguals to understand cognitively demanding mathematical problems through task modification. Fieldwork with a concurrent intervention was designed for the PSTs to work with emergent bilinguals in a one-on-one setting. The PSTs modified cognitively demanding mathematics tasks and designed a lesson for the emergent bilinguals based on the modified tasks. The results revealed that the task modification made by the PSTs tended to shift from reducing cognitive demands in mathematics and language to maintaining the demands through learning strategies of contextual support.