As work organizations restructure to remain competitive, problem solving is being pushed down to frontline workers, and emphasis is increasingly placed on workplace learning. In this exploratory, qualitative study, we focus on workers' experiences of problems within the context of their work and how these contexts foster their learning and development. To that end, we examined the informal learning processes associated with problem-solving contexts among twenty manufacturing workers from three organizations. The findings suggest that operators perceive learning to be integral to problem solving, relational and dialogical in nature, and intimately bound up with an evolving machine operator identity. This research also holds implications for problem-solving training within the workplace, the role of managers and supervisors in relation to the development of expertise, the role of the human resource professional as adult educator, and the role of adult educators in general.