In this paper, we describe how Masters students at a university studying Information Systems adapt to Enterprise Modelling; expressed metaphorically, they come out of their UML tunnels and see the world outside. The paper describes an overview of the course and the results and observations of the course based on the modelling assignments submitted by the students. The main observation is that while students are able to conceptualise a situation and represent that as an Enterprise Model, they often lack the experience to clearly state the purpose of the model and therefore, lack the ability to evaluate their models appropriately. Based on the experiences of teaching Enterprise Modelling to Information Systems students, the paper also provides a set of recommendations for teachers.