The field of Artificial Intelligence in Education (AIED) has undergone significant developments over the last twenty-five years. As we reflect on our past and shape our future, we ask two main questions: What are our major strengths? And, what new opportunities lay on the horizon? We analyse 47 papers from three years in the history of the Journal of AIED (1994, 2004, and 2014) to identify the foci and typical scenarios that occupy the field of AIED. We use those results to suggest two parallel strands of research that need to take place in order to impact education in the next 25 years: One is an evolutionary process, focusing on current classroom practices, collaborating with teachers, and diversifying technologies and domains. The other is a revolutionary process where we argue for embedding our technologies within students’ everyday lives, supporting their cultures, practices, goals, and communities.