The legislative process is the backbone of a state built on solid institutions. Yet, due to the complexity of laws -- particularly tax law -- policies may lead to inequality and social tensions. In this study, we introduce a novel prototype system designed to address the issues of tax loopholes and tax avoidance. Our hybrid solution integrates a natural language interface with a domain-specific language tailored for planning. We demonstrate on a case study how tax loopholes and avoidance schemes can be exposed. We conclude that our prototype can help enhance social welfare by systematically identifying and addressing tax gaps stemming from loopholes.