The objective of this paper is to present the findings and a set of hypotheses that emerged in the initial steps of an assessment study of air traffic controllers’ adoption and adaptation of new technologies, with the user request evaluation tool (URET) as a case study. The hypotheses are the basis for further study on this topic. The importance of this investigation is to provide a better understanding of changes brought about by the use of decision support tools by sector controller teams. The main purpose of URET is to support sector team strategic planning and allow controllers to concentrate on more user-beneficial control actions. Actual improvements depend on the way controllers use the automation tools in their work. Three aspects were noted about URET usage: (a) different sector teams use it in different ways, (b) in many instances URET usage differs from what was intended, and (c) usage varies across centers. Subject matter experts were interviewed to explore how controllers have adopted and adapted URET across the mentioned variations. The goal of this research is to draw lessons from the experience with URET that can inform technology deployments in the future.