Checking the compliance of software against laws, regulations and contracts is increasingly important and costly as the embedding of software into societal practices is becoming more pervasive. Moreover, the digitalised services provided by governmental organisations and companies are governed by an increasing amount of laws and regulations, requiring highly adaptable compliance practices. A potential solution is to automate compliance using software. However, automating compliance is difficult for various reasons. Legal practices involve subjective processes such as interpretation and qualification. New laws and regulations come into effect regularly and laws and regulations, as well as their interpretations, are subjected to constant revision. In addition, computational reasoning with laws requires a cross-disciplinary process involving both legal and software expertise. This paper reflects on the domain-specific language eFLINT developed to experiment with novel solutions to these challenges. Specifically, the language has been developed to experiment with the abstract syntax and semantics of a language supporting different types of reasoning for various applications. The language combines declarative and procedural elements, formalises connections between legal concepts and computational concepts, and is designed to automate compliance checks before, during and after a software system runs. The various design goals and applications areas for the language give rise to (conflicting) requirements. This paper presents and reflects on the current design of the language by recalling applications and requirements. As such, this paper reports on results and insights of an investigation that can benefit language developers within the field of automated compliance.

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