This conceptual work focuses on service ecosystems dynamics, since they can be crucial for innovation, resilience, and sustainability. Specifically, in this chapter these dynamics have been considered in relation to actors’ perspectives and perceptions on service ecosystem complexity and frictions. Recognizing the importance of such elements in the evolution of service ecosystems, it offers a framework for matching the three service ecosystem complexity states (ordered, manageable, and free complexity), the most common frictions (dilemmas, trade-offs, and paradoxical tensions), and the main systems dynamics drivers (emergence and institutionalization). It also provides illustrations in the realm of healthcare systems and their relations with digitalization and new technologies. The study offers labels for contexts and supports the selection of strategies to cope with complexity and related frictions to both academics and practitioners.