Air traffic controller workload is a limiting factor in the current air traffic management system. Adaptive support systems have the potential to balance controller workload and gain acceptance as they provide support during times of need. Challenges in the design of adaptive support systems are to decide when and how to trigger support. The goal of this study is to gain empirical insights into these challenges through a human-in-theloop experiment, featuring a simplified air traffic control environment in which a novel triggering mechanism uses the quality of the controller's decisions to determine when support is needed. The designed system seeks to prevent high workload conditions by providing resolution advisories when the controller exceeds a threshold of "self-complicating" decisions. Results indicate that the new system is indeed capable of increasing the efficiency and safety compared to full manual control without intervention. More adaptive support, however, increased the frustration of participants, decreased acceptance, and did not result in improved workload ratings. These findings suggest that, unless we can better infer human intent in complex work environments, adaptive support at the level of decision-making is problematic. A potentially more fruitful direction is to provide support at the level of information integration, with full decision-making authority with the human.