Deep reinforcement learning using convolutional neural networks is the technology behind autonomous vehicles. Could this same technology facilitate the road to college? During the summer between high school and college, college-related tasks that students must navigate can hinder successful matriculation. We employ conversational artificial intelligence (AI) to efficiently support thousands of would-be college freshmen by providing personalized, text message-based outreach and guidance for each task where they needed support. We implemented and tested this system through a field experiment with Georgia State University (GSU). GSU-committed students assigned to treatment exhibited greater success with pre-enrollment requirements and were 3.3 percentage points more likely to enroll on time. Enrollment impacts are comparable to those in prior interventions but with substantially reduced burden on university staff. Given the capacity for AI to learn over time, this intervention has promise for scaling personalized college transition guidance.