This research explores how inter-organizational relationship interacts with factors affecting the development and implementation of information sharing. On the basis of the resource-based view and relational risk perspective, we developed a model which comprises three research hypotheses with three constructs, including relational benefits, relational risk, and information sharing. The constructs are measured by well-supported measures in the literature. Structural equation modeling was used to analyze survey data collected from 528 manufacturing firms that were among the top 1,000 Taiwanese manufacturing firms of 2011 listed by Business Weekly. The results of the empirical study suggest that relational benefits are critical in ensuring information sharing and mitigate relational risk in the process. The findings of the study provide useful insights into how supply chain members can reinforce their relational benefits and mitigate probable risks so as to improve their collaborative behaviors and in turn enhance information sharing for the supply chain as a whole.