Information system (IS) procurement history is replete with poorly executed, multimillion dollar procurement decisions. Yet we barely understand what effective IS procurement should look like. IS procurement is highly challenging, as it requires the client to simultaneously select a technology and vendor. This paper explores the technology-vendor selection process through the sensemaking perspective. Our study develops a sensemaking model for technology-vendor selection that connects the multiple rounds of client-vendor communicative actions with the client's sensemaking process. We show how the client reconciles fragmented and sometimes conflicting cues and information through three intertwined cycles: immediate, retrospective, and decision. Sensebreaking occurs as a separate process (and not a communicative action) when disruptive cues occur persistently and from different vendors over multiple rounds of sensemaking. We derive a set of critical factors, on the basis of the sensemaking perspective, for selecting an appropriate vendor and technical solution. These insights in turn help explain many poorly executed IS procurement decisions.