The present study uses event-related potentials to investigate how crosslinguistic (dis)similarities modulate anticipatory processing in the second language (L2). Participants read predictive stories in English that made a genitive construction consisting of a third-person singular possessive pronoun and a kinship noun (e.g., his mother) likely in an upcoming continuation. The possessive pronoun?s form depended on the antecedent?s natural gender, which had been previously established in the stories. The continuation included either the expected genitive construction or an unexpected one with a possessive pronoun of the opposite gender. We manipulated crosslinguistic (dis)similarity by comparing advanced English learners with either Swedish or Spanish as their L1. While Swedish has equivalent possessive pronouns that mark the antecedent?s natural gender (i.e., hans/hennes ?his/her?), Spanish does not. In fact, Spanish possessive pronouns mark the syntactic features (number, gender) of the possessed noun (e.g., nosotros queremos a nuestra madre ?we-MASC love our-FEM mother-FEM). Twenty-four native speakers of English elicited an N400 effect for prenominal possessives that were unexpected based on the possessor noun?s natural gender, consistent with the possibility that they activated the pronoun?s form or its semantic features (natural gender). Thirty-two Swedish-speaking learners yielded a qualitatively and quantitatively native-like N400 for unexpected prenominal possessives. In contrast, twenty-five Spanish-speaking learners showed a P600 effect for unexpected possessives, consistent with the possibility that they experienced difficulty integrating a pronoun that mismatched the expected gender. Results suggest that differences with respect to the features encoded in the activated representation result in different predictive mechanisms among adult L2 learners.