According to the Shallow Structure Hypothesis (SSH), second language (L2) speakers, unlike native speakers, build shallow syntactic representations during sentence processing. In order to test the SSH, this study investigated the processing of a syntactic movement in both native speakers of English and proficient late L2 speakers of English using pupillometry to measure processing cost. Of particular interest were constructions where movement resulted in an intermediate gap between clauses. Pupil diameter was recorded during auditory presentation of complex syntactic constructions. Two factors were manipulated: syntactic movement (such that some conditions contained movement while others did not), as well as syntactic movement type (either causing an intermediate gap or not). Grammaticality judgments revealed no differences between the two groups, suggesting both were capable of comprehending these constructions. Pupil change slope measurements revealed a potential sensitivity to intermediate gaps for only native speakers, however, both native and late L2 speakers showed similar facilitation during processing of the second gap site. Acoustic analysis revealed potential acoustic cues that may have facilitated the processing of these constructions. This suggests that, contrary to the predictions of the SSH, late L2 speakers are capable of constructing rich syntactic representations during the processing of intermediate gap constructions in spoken language.