Success in postsecondary education requires students to engage with their institution both academically and administratively. As with the transition to college, administrative requirements students face once enrolled can be substantial. Missteps with required processes can threaten students’ ability to persist. During the 2018-19 academic year, Georgia State University implemented an artificially intelligent text-based chatbot to provide proactive outreach and support to help undergraduates navigate administrative processes and take advantage of campus resources. A team of centralized university administrators orchestrated outreach “campaigns” to support students across three broad domains: (1) academic supports; (2) social and career supports; and (3) administrative processes. We investigate GSU’s implementation of this persistence-focused chatbot through an experimental study. Of the three message domains, outreach was most effective when focused on administrative processes, many of which were time-sensitive and for which outreach could be targeted specifically to students for whom it was relevant based on administrative data. In contrast, outreach to encourage take up of other supports had little effect on student behavior. By the end of the academic year, rates of FAFSA filing and registration for the subsequent fall semester were approximately three percentage points higher, suggesting positive effects on year-to-year college persistence. The positive effects on fall enrollment persisted into summer 2019, at which time the GSU administration judged that the study results were compelling enough to conclude the experiment and roll the chatbot system out to all students. We situate our findings in the literature on nudge-type efforts to support college access and success to draw lessons regarding their effective use.