College success requires students to engage with their institution both academically and administratively. Missteps with required processes can threaten students’ ability to persist. We experimentally assessed the effectiveness of an artificially intelligent text-based chatbot to provide proactive outreach and support to college students to navigate administrative processes and use campus resources. In both the two-year and four-year college context, outreach was most effective when focused on administrative processes which were acute, time-sensitive, and for which outreach could be targeted to those for whom it was relevant. We draw lessons regarding the effective use of nudge-type efforts to support college success.