Continuous business, technical, and regulatory changes constantly force organizations to transform. Enterprise Architecture Management (EAM) is a means to plan, conduct, and coordinate these complex transformations by providing a holistic view, a common vocabulary, and a solid decision base. And yet, with issues like a decoupling between requirements and final results, a long delivery period, or unappreciated value, the discipline of EAM is not immune to domain-specific challenges. While literature from an academic and practitioner authorship acknowledges these issues, the actual occurrence, pervasiveness, and degree of relevance from an industry standpoint remains unclear. More precisely, the question whether, how, and to which extent organizational factors like an organization’s size or its experience in EAM exert influence on these challenges has not been answered on empirical basis yet. This paper is set out to clear up this nebulous state by means of an expert survey which involved 105 industry participants from 50 international organizations located in 10 different countries. The results underline the situational character of the management discipline with respect to the challenges it is confronted with.