In an increasingly digital world driven by artificial intelligence, the importance of instilling empathy in future lawyers cannot be overstated. As technology continues to evolve, so too should our methods of teaching empathy to the next generation of lawyers. This session proposes an exploration of teaching empathy through the lens of document assembly—a critical tool in combating the access to justice crisis and one in which CALI has unique expertise. Automated legal forms help more than 1 million people a year to learn about their legal rights, complete the necessary court paperwork, and tackle the justice system pro se. By leveraging technology in innovative ways, we can not only streamline court form automation, but also foster a deeper understanding of the human beings struggling to access the justice system on their own. This session will delve into practical strategies and tools for integrating empathy into document assembly processes, ensuring that our advancements in AI remain grounded in human understanding and compassion.