As supply chains evolve beyond the confines of individual organizations, collaboration has become the Holy Grail in supply chain technology. It plays a key role in achieving flexibility and responsiveness. Information sharing between partners is a key determinant of collaboration. This paper investigates information sharing in four different supply chains—3PL, VMI, CPFR, and supply networks—and compares their information sharing structures, shared data objects, and information flow models. The results show how the various parameters of an information flow model constrain the level of collaboration. Further, the modeling exercise provides insights on how to configure a collaborative supply chain by leveraging information sharing.