In our Panel Discussion, we explore whether Jamaica’s education system is approaching a crossroads with higher than normal attrition rates amongst teachers locally and abroad, coupled with disruptive technologies offering new methods of accessing education. We explore how a centuries-old system of learning is adapting to changes in the modern world with Senator Damion Crawford Opposition Spokesperson on Education, Training, and Competitiveness, and Diaspora Consultant and Former Vice-President of Jamaica Press Association (PAJ) Hylton Dennis.