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 paper 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.