This study provides the first longitudinal examination of the development of Spanish direct object clitic pronouns (i.e., lo(s)/la(s) or le(s)) by English-speaking learners of Spanish in a study abroad context in León, Spain. The data come from 33 non-native speakers (NNSs) of Spanish participating in a highly selective honors immersion program for incoming high school seniors and from 24 native speakers (NSs) of Spanish residing in León, Spain. All participants completed a background questionnaire, a level test, and a 65-item contextualized preference task in which 24 items specifically targeted direct object clitic pronouns. The NNSs completed the level test at the beginning and end of their stay abroad and a different version of the written contextualized task at three different points in time (week 1, week 4, and week 7). The NSs completed each task only once. The results show that initial NNS rates of selection of le(s) were similar to NS rates; however, the linguistic predictors of this selection were different. Over time, NNSs showed a sharp decrease in selection of le(s) followed by a gradual increase toward NS rates. In terms of the linguistic factors that influence selection of le(s), NNSs approximated NS norms over time. Most generally, the paper's results serve to extend the current understanding of the SLA of variable structures to a new grammatical construct and also to the study abroad context.