The current study explores the challenges faced by English for specific purposes (ESP) program at University of Muhammadiyah Malang (UMM), Indonesia. As a part of their commitment to improvement, this university is working to better prepare students for employment so that they may function well in their workplaces. Currently, many English Department graduates apply and are accepted as ESP teachers. However, their pedagogical knowledge of ESP teaching is deemed to be less than adequate for such purposes. To do this, classroom observation and interviews were undertaken to explore the multiple realities of the three groups of stakeholders at this institution--the management, ESP teachers, and students. The findings showed four aspects which ought to be crucially applied in ESP classrooms but are relatively absent. Those are communication focus, learner-centred, collaborative teaching, and practical and authentic materials. Since several aspects of ESP teaching are not quite similar to teaching General English (GE), but GE still can be included to support the ESP teaching, the Director of Language Centre (LC) needs to reconsider the type of ESP fits in the contexts, and teachers who are willing to deal with these classes need to understand and possibly be given and trained intensively in relation to its pedagogy.