The chapter reflects on the author’s experience of teaching asynchronously master’s level elementary mathematics education courses with problem-posing assignments and prompts offered for discussion. The chapter suggests investigating the role of the Einstellung effect, typically associated with errors in problem solving, in the context of problem posing. Several problems posed by teacher candidates are analyzed and remedial strategies aimed at the improvement of problem-posing skills are recommended. The chapter shows how classic mathematical and pedagogical perspectives on problem posing can be brought to light as one reads the modern-day views on the topic of the book expressed by in-service and preservice elementary teachers through responses to discussion prompts.