Currently the documentation of an Enterprise Architecture (EA) is performed manually to a large extent. Due to the intrinsic complexity of today’s organizations this task is challenging and often perceived as very time-consuming and error-prone. Recent efforts in research and industry seek to automate EA documentation by retrieving and maintaining relevant information from productive systems. In this pa- per major challenges for an automated EA documentation are presented based on 1) a practical example from a global acting enterprise of the German fashion industry, 2) a literature review, and 3) a survey among 123 EA practitioners. The identified challenges are synthesized to four categories and constitute the foundation for future research efforts and pose new questions not yet considered.