Complex systems increasingly include embedded digital technologies that interact with and are constrained by physical components and systems. Although these systems play a central role in our society, they have only been scarcely addressed in contemporary research on digital transformation and the organization of innovation. This article explores the digital transformation in complex products and systems and its consequences for organizational design. A longitudinal study of avionics development since the 1950s uncovers the application of digital technologies, first as a sequence of initial experiments, followed by the use as add-on functionality, then as an integral part of achieving critical functionality in systems, and currently combining add-on and critical functionalities enabling generativity. The findings emphasize the evolution of the intricate relationships between the systems architecture and organizational approaches when digital technology enables and enforces increased complexity, expanded functionality, increased systems integration, and continuous development. These nested dependencies are accentuated by the complexity that has emerged beyond human cognition, where increasingly sophisticated boundary objects based on modeling, simulation, and data play an important role in the organization's ability. Boundary objects relate and decouple the multifacetted dynamic relation between organization and architecture. The results also extend existing perspectives on platform strategies by outlining the importance of generativity in combination with criticality control, rather than market control. Criticality control in combination with generativity has become imperative not least as generative digital technologies have become central in achieving critical properties such as safety. Several avenues for further research are outlined.