Incumbents are increasingly establishing digital ventures to explore the potential of digital technologies, yet this introduces unique tensions and management challenges. Focusing on the case of German insurance company DEVK and its digital subsidiary freeyou, our study delves into the complexities and tensions prevalent in such associations. Through a longitudinal study encompassing interviews, archival data, and observations over seven years, we offer detailed insights into the development, intertwinement, and management of these tensions. Our research contributes to understanding the nuanced interplay of tensions in digital ventures within established firms, addressing a gap in both academic discourse and practical application in the field of digital venturing and digital innovation.