Questions we care about: Why do undergraduates appear to struggle with the application of effectuation principals and processes? How can we engage undergraduate students in effectuation processes in the entrepreneurship classroom to achieve the best possible learning? Approach: This research paper is based on a data from a third semester Organizational Innovation process course with 142 undergraduate students which represents an extreme case. As teachers and researchers we had a double role; being insiders and outsiders. Being teachers we had ready access to a range of data from the students. Being researchers we were able to use participant observations and data from teacher meetings to provide an in-depth analysis of the field and explore the extent to which effectuation processes are enacted and understood by students and examine underlying barriers and drivers. Results: Our goal was to understand why the majority of undergraduates, who were excited and motivated to become effectual, struggled to apply, understand and reflect deeply on effectuation principals. We identify four barriers to being effectual in an innovation process. Firstly undergraduate students are novices in a number of ways; as students, as people, as entrepreneurs and as team players. Secondly the end product is regarded as a ‘school’ project and not a real life opportunity. Thirdly lack of trust at different levels and finally the extent to which students perceive the teachers as experts hindered their involvement. Implications: For teachers of entrepreneurship recognition of the four barriers to the application of effectuation principals may be helpful to understand why students fail to achieve the learning outcomes we set when effectuation is used as a principle and practice. As trust is an antecedent to the success of applying effectuation it must be considered as a critical element from the initial meeting with the students. Teaching undergraduate students presents a range of challenges and teachers of entrepreneurship need to carefully consider how they approach teaching of effectuation in the classroom. Value/Originality: This paper makes a two important contributions: First, we add to the literature on entrepreneurship education by informing the gap in our understanding of the mis-match between what we want to achieve and what we actually achieve in our classrooms when teaching effectuation. Second, we contribute to the discussion of how novices can be enabled to enact effectuation principal by pointing to the importance of contextual factors.