The relationship quality between client and vendor organizations is one of the most significant influence factors for IT outsourcing success. In this context, the degree of dissimilarity between cultural values of two or more organizations (“cultural distance”) can represent a considerable challenge for establishing and maintaining good-quality relationships. Still, research on cultural distance and its effects is scarce. This paper seeks to address this gap. Building on extant theory on culture and IT outsourcing, we develop a research model which we are currently evaluating. This is done by means of an exploratory, qualitative research design based on an in-depth single case study that analyzes three outsourcing configurations of a leading European media company. Their diversity allows for a detailed examination of cultural distance on the national, organizational, and team level. Given its highly relevant characteristics, we expect our research to yield valuable contributions for both theory and practice.