Based on action research of the Information Processing (IP) course at the bachelor programme HA/DOK at Copenhagen Business School, we investigate which barriers students experience when learning holistic systems development and why. HA/DOK has been developed to educate students who can facilitate between users and programmers and navigate within and between the application (i.e. the users') and the problem (i.e. the IT system's) domain. However, a summative evaluation suggests a gap between the study programme's intention and the students' learning and performance at the IP exam. Our investigation of this gap reveals that while the students readily think and act in accordance with the problem domain they all struggle to achieve the learning objectives that concern the application domain. We propose that the students' difficulties arise as a consequence of how the study programme is designed and outline alternatives for helping them overcome the barriers and/or reach the learning objectives. (Contains 3 tables and 1 figure.)