Edifii is a personalized digital school counselor that empowers both students and counselors, delivered as a mobile/web app for students and counselors. Classical and generative AI systems customized for high school counseling work in tandem with a streamlined ‘discovery process’ to learn about a student’s particular background and offer personalized planning guidance, or ‘path charting’ via a chatbot interface. Edifii is an always available and well-informed counselor ready to help with step-by-step guidance towards career and college goals. Edifii also provides valuable information to counselors to make even short interactions with students as effective as possible.