The work world is set to undergo major changes thanks to advancements in automation and artificial intelligence and is beginning to promote new forms of collaboration. The transition from a technologysupporting environment to a collaborative environment in which people and technology work together to achieve their goals requires a fundamental change in the way we design, build, and ultimately deploy information systems. Most work on information system design focuses on the effective augmentation of humans. However, little is known about constructing a sustainable mutually beneficial collaboration between human and machine. To better understand this relationship, we perform a case study drawing on ethnographic evidence collected during a multi-year design science research project with a major service provider for unit load device management in the air cargo industry that resulted in an artifact for human-machine collaboration (HMC). Our study takes a closer look at the co-evolution that emerges from the collaboration between human and artificial agents over time, in which both parties influence each other, the underlying tasks, and their environment. Our analysis reveals three facets of symbiotic co-evolution: agents' evolution, activity evolution, and structural evolution. The findings contribute to the HMC knowledge base and have implications for future HMC design initiatives.