Abstract Ensuring compliance of software systems with government regulations, policies and laws is a complex problem. Generally speaking, solutions to the problem first identify rights and obligations defined in the law and then treat these as requirements for the system under design. This work examines the challenge of developing tool support for extracting such requirements from legal documents. To address this challenge, we have developed a tool called GaiusT 1. The tool is founded on a framework for textual semantic annotation. It semi-automatically generates elements of requirements models, including actors, rights and obligations. We present the complexities of annotating prescriptive text, the architecture of GaiusT, and the process by which annotation is accomplished. We also present experimental results from two case studies to illustrate the application of the tool and its effectiveness relative to manual efforts. The first case study is based on the US Health Insurance Portability and Accountability Act (HIPAA), while the second analyzes the Italian accessibility law for information technology instruments. Keywords semantic annotation · legal documents · requirements engineering · regulatio
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