Despite the benefits and huge advances in (aviation) automation over the last decades, the current automated tools are in many cases unaware of the ‘bigger picture’. That is, they are not yet able to understand the intentions of users or the intricacies of the environment it is operating in. When the level of automation support in future air traffic control increases, the automated systems will need more awareness about the dynamic context in which they operate. The broad aim of this research is to provide fundamental insight into, and practical experience with, the difficult challenge of adaptive automation and level of automation transitioning in a human-centred air traffic control work environment. An innovative element in this research project is the development of autonomous, environmentally-driven adaptive automation, where the appropriate level of automation will be determined by the functional demands of the operational context. The goals are: (1) to discover the metrics that constitute an operational context, and (2) to develop a rule base for level switching and human-machine interface adaptation.