College success requires students to engage with their institution academically and administratively. Missteps with required administrative processes can threaten student persistence and success. Through two experimental studies, we assessed the effectiveness of an artificially intelligent text-based chatbot that provided 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 discrete administrative processes such as filing financial aid forms or registering for courses which were acute, time-sensitive, and for which outreach could be targeted to those for whom it was relevant. In the context of replicating studies to better inform policy and programmatic decision making, we draw three core lessons regarding the effective use of nudge-type efforts to promote college success.