When acquiring information systems, public entities face a dilemma. On the one hand, they want to procure the system that best suits their needs, which often requires lengthy dialogues with vendors. At the same time, they are restricted by government regulations that mandate limited dialogue in the interests of transparency and equal opportunities for all vendors. To examine how public entities deal with this, we followed three procurement projects in Norway. We show that this dilemma manifests itself as a dialectic between the thesis of getting the system requirements right and the antithesis of strictly adhering to regulations. Public entities search for a resolution of this dialectic through two syntheses: selecting an appropriate tendering procedure, and learning how to specify requirements through networks of peer public entities. Our findings reveal that the syntheses are possible because the dialectic is actually complimentary, both the thesis and the antithesis are needed to create the joint outcome that satisfies both. The resolution of the dialectic unfolds differently over time. Our study contributes to the relatively neglected stream of IS research on dialectics that explicitly searches for a synthesis while revealing the complementarity of the dialectic. We show how time plays a nuanced role in the resolution of the dialectic situation.