Contextual ambidexterity of an interorganizational relationship IOR is the ability of its management system to align partners’ activities and resources for short-term goals and adapt partners’ cognitions and actions for long-term viability. It is an alternative to structural ambidexterity in which separate units of the IOR pursue short-and long-term goals. We theorize that when utilized to coordinate the IOR, information technology IT-enabled operations and sensemaking, along with interdependent decision making, promote the IOR’s contextual ambidexterity. We test our hypotheses on both sides of a customer-vendor relationship using data collected from 1 the account executives of one of the world’s largest supply chain vendors n = 76 and 2 its customers n = 238. We find commonalities and differences in the influence coordination mechanisms have on contextual ambidexterity from the vendor’s and the customer’s perspectives. For both customers and vendors, contextual ambidexterity improves the quality and performance of the relationship, and decision interdependence promotes contextual ambidexterity. For customers, using operations support systems OSSs and interpretation support systems ISSs enhances contextual ambidexterity. For vendors, the impact of both OSS use and ISS use on contextual ambidexterity depends on the duration of the relationship. Our study shows that IT-enabled operations and sensemaking are key enablers of IOR ambidexterity and that vendors should combine these IT capabilities with relationship-specific knowledge that accumulates with relationship duration.