Just as human operators are important production enablers in the factories of today, they are expected to stay key enablers also in future manufacturing. In today’s factories, operators often meet challenges related to poor information and communication design, which affects their possibilities to perform with higher efficiency levels. Therefore, they need to be provided with better cognitive support tools that are relevant to the challenges to be met. To ensure efficient and effective operator work in the factories of the future, operator support needs to be adequate for the new tasks arising from the evolving operators’ roles and work. Within this paper, the results of current operators’ work and challenges, based on six case studies, are combined with an outlook of the future of work of operators, based on the Operator 4.0 vision. The challenges categorized in this paper can be used to identify opportunities for improvement in the operators’ cognitive support in present factories as well as for researchers and developers of Operator 3.0 support solutions.