The irruption of artificial intelligence in the legal field has an impact on several issues. In this research we analyze its potential for contractual interpretation. We perceive difficulties that challenge its results, which are qualitatively comparable to those produced by human intelligence. The main objection seems to be the discretionary nature of contract interpretation. It translates into the coexistence of four different more/less creative approaches (backgrounds) that must be justified. For Artificial Intelligence to justify such inclinations, good questions are required to define the trajectories that the algorithms should follow. We argue that, for the time being, collaboration between the two types of intelligence is the most appropriate.