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Transport Canada is reviewing its Aviation Security regulations in a multi-year modernization process. As part of this review, consideration is given to transitioning regulations where appropriate from a prescriptive style to an outcome-based style. This raises new technical and cultural challenges related to how to measure compliance. This paper reports on a novel approach used to model regulations with the Goal-oriented Requirement Language, augmented with qualitative indicators. These models are used to guide the generation of questions for inspection activities, enable a flexible conversion of real-world data into goal satisfaction levels, and facilitate compliance analysis. A new propagation mechanism enables the evaluation of the compliance level of an organization. This outcome-based approach is expected to help get a more precise understanding of who complies with what, while highlighting opportunities for improving existing regulatory elements.