Artificial Intelligence (AI) has revolutionized the field of GIS, but is still being grappled with in education. We know that both students and the workforce are using AI, yet are uncertain of its long-term impacts on learning and socio-environmental systems. At Dartmouth College, the Geography Department has been exploring AI technologies in GIS classes from introductory to advanced and assessing their impact on student learning. This presentation offers our experiences, findings, and points of discussion for a new technological future.