This paper examines the relationship between organizational buyers’ ex-ante or pre-contract perceptions of opportunism and technological uncertainty and the resulting impact on core vendor outcomes. Specifically, the paper examines whether pre-contract perceptions of opportunism and technological uncertainty negatively affect outsourced service providers’ ability to establish a relationship with organizational buyers. Both opportunism and uncertainty have been manifested as key tenets in inter-firm exchanges. Extant literature defines opportunism as both ex-ante (pre-contract) and ex post (post-contract). However, existing research does not provide guidance on whether buyers’ ex-ante or pre-contract perceptions of opportunism and technological uncertainty adversely affect vendors’ ability to: 1) win business/contract, and 2) how it influences the post-contract buyer-supplier relationship dynamics. The research model is tested on an online panel of information technology (IT) buyers across a range of industries. Findings favor outsourced vendors in that there isn’t a relationship between buyers’ ex-ante perceptions of opportunism and their willingness-to-engage in a contractual relationship with a provider. Furthermore, while previous scholarly research stream found positive connection between technological uncertainty and willingness of buyers to work closely with suppliers, the findings of this study reveal that buyer cooperation is not automatic. It is important to note that the term vendor is rather broad-based in scope and represents a variety of inter-firm arrangements across manufacturing and services sectors, therefore, the implications of this study extend far beyond the traditional transaction cost analysis framework to include vendor selection and post-contract vendor management.