The digitalization of the newspaper industry represents a significant challenge for incumbent companies to engage new technologies. Many companies in the industry have had to seek new markets through digital technologies to survive. This paper explores how one of the largest Swedish newspapers, Aftonbladet, has strategically embraced new media and new markets. We report a decade of engaged scholarship based on interviews and archival analysis that covers 20 years of strategic acts at the company. We consider this effort as a case of organizational ambidexterity under digitalization. The analysis seeks to extend theoretical understanding of the interrelationships between strategic intent and technological choice. The paper contributes to the understanding of ambidexterity under digitalization by theoretically framing it in terms of strategic acts. The research suggests that digitalization implies a more complex ambidexterity interrelationship between old and new markets and technologies. As digitalization enables the loosening of previously tight couplings, the clear theoretical distinction between old and new, and critically, the unproblematic transition, is brought into question. The paper suggests replacing the notion of an orderly shift from the old to the new with ambidexterity under digitalization as a duality of both old and new undergoing continual reconfiguration. © 2018 Elsevier Ltd