Changes in the global market have posed critical challenges for industrial districts and increased competition. In such a context, adopting information and digital technologies has become essential for district firms to innovate products and processes, effectively manage the relationships along the value chains, and achieve or sustain a competitive advantage. The adoption of digital technologies (DTs) requires district firms to have some specific enabling characteristics, which may depend on their interactions within the district environment and which are still a matter of debate. To increase knowledge on this topic, the present research investigates the path that enables district firms' technology adoption processes by examining how cognitive and affective trust relate to tacit knowledge sharing, which, in turn, affects the technological and organizational factors determining DT adoption. Through structural equation modeling, the results of a survey study on footwear district firms highlight that cognitive trust—but not affective trust—influences both the technological and organizational factors through tacit knowledge sharing. Theoretical and operational implications are discussed.