This study investigates the degree to which native-English-speaking learners of Spanish can generate expectations for information likely to occur in upcoming portions of an unfolding linguistic signal. We examine Spanish clitic left dislocation, a long-distance dependency between a topicalized object and an agreeing clitic, whose felicity depends on the discourse. Using a self-paced reading task, we tested the predictions of the shallow structure hypothesis (Clahsen & Felser, 2006a, 2006b) and the reduced ability to generate expectations hypothesis (Grüter, Rohde, & Schafer, 2014). Learners successfully demonstrated sensitivity to the violation of expectations set up by the syntactic and discourse context. In addition, the behavior of the second language (L2) learners was dependent on proficiency: the higher their proficiency, the more their behavior mirrored native-speaker processing. These results support a view of SLA in which knowledge of L2 discourse-grammatical relationships is acquired slowly over the course of L2 learning.