Massive Open Online Courses (MOOC) are becoming a popular educational tool in different disciplines. Urban planning education is no exception and new MOOCs are being released every year. Despite this, it is still not clear how this new learning experience is being developed, delivered, and impacting upon planning education. This article sheds light on this issue using the case of the Rethink the City MOOC organised by the Faculty of Architecture and the Built Environment of TU Delft. The course received the AESOP Excellence on Teaching award in 2017 and serves as an example of how planning education is facing the change towards online education. The article briefly introduces the course and develops on the challenges and results of it. Based on the course team experience of preparing and delivering the course, the article contributes to the debate about online education and supports fellow academics involved with the creation of new MOOCs.