In their search for differentiation, customer value, and profit margins, companies practice digital servitization or digital service innovation (DSI). However promising, this road to smarter and more sustainable product service systems is paved with complex challenges which seem to be underestimated by researchers and managers. In order to succeed in this value-adding strategy, the main literature suggests alignment and change management during the digital service transition. Faced by a growing number of digital transformation process issues, DSI researchers and servitizing companies could benefit from a new theoretical lens, building on the perspectives of complex adaptive systems (CAS) theory. The resulting framework can inspire managers to perceive the complexity of the DSI process and build the necessary capabilities and mechanisms to cope effectively with it. Researchers can learn how to use CAS theory to “decipher” DSI complexity and help managers cope with the latter.