As the legal industry more readily leverages software for tools, automation, and predictive analytics, it has increased the affordable access to justice and legal services for underserved populations, helping make information and knowledge available for all. FOSS has and will continue to play a critical role in this evolution, but the line between where such software's functionality ends and the practice of law begins remains fuzzy. This presentation will discuss some of the legal precedent around Unauthorized Practice of Law (UPL) enforcement related to software, and will explore how current and future UPL enforcement may align or conflict with FOSS principles.