This paper draws on both Adult Educators’ (AE) observations of and learners’ experiences with the Productive Failure (PF)-infused lessons. In applying the PF Design principles (DPs) to lessons for learners from various sectors, this paper elaborates on the benefits and challenges faced by both AEs and their learners. Seven AEs from different sectors, e.g., healthcare, early childhood, security, professional development, participated in this project with about 150 learners involved in two pilot lessons.