Today’s enterprise environment is more sophisticated than ever and being able to manage this complexity is not possible without having a planned approach. Enterprise architecture (EA) has emerge as a planned approach to mitigate the organizational complexities and control the constant environmental changes. How-ever, despite the numerous EA development step-by-step methods and approaches not all of the EA efforts end with success. In this study we aimed to identify the obstacles that endanger the EA projects. Employing the multiple case study research method we collected data from 14 large enterprises by interviewing 20 experts. In total, we identified 20 obstacles that we further categorized into four main themes. Compared to earlier literature we found five types of obstacles that have not been mentioned before: political issues of the government, EA consultant related issues, outdated organizational statutes, constant change of management, and inefficient human resource department. Further we discussed about the relationships among the identi-fied obstacles and provide advice for managers to reduce the obstacles during EA development. Because this study is based on real world cases, provided understanding can benefit practitioners to alleviate obstacles during EA development.