Test Automation is essential to increase the effectiveness, efficiency and coverage of software testing activities with reasonable effort which is required to keep up in a fast-paced industry with a growing demand for high quality software products. Nevertheless adopting test automation is a difficult task for development organisations. Automating the testing process for application landscape frameworks is especially hard due to the complexity caused by the variety of customer application landscape configurations, used tools and platforms. This complexity often is hard or impossible to reduce due to given domain constraints, e.g. limited resources of embedded systems and different platforms that have to be supported. In addition, existing hardware and software systems in the customer’s application landscape require rather flexible solutions and configuration options for different customers. In this paper we present some major challenges adopting test automation for application landscape frameworks, as research shows that this is especially difficult for such highly configurable systems. Furthermore initial ideas on how to cope with these challenges are outlined.