Digitalization has created service business opportunities for machine manufacturing companies. But creating these cyber-physical systems of systems effectively constitutes a critical measure of success in practice. At the same time, the body of knowledge in software engineering provides little guidance on how to manage this evolution. To contribute to closing this gap in the long run via problem-driven research, we need to first understand which contemporary challenges and needs are encountered in industry. To this end, we conducted a series of semi-structured interviews at a machine manufacturing company, that is expanding its service offerings utilizing digitalization, where we explored how such systems are engineered and what challenges and needs are encountered. © 2023 IEEE.