During the recent “Effective Settlement Advocacy: Pro Se Litigants’ Settlement Assistance Program”, the Federal Bar Association Chicago Chapter discussed effective settlement advocacy and pro bono service in federal court. Held at the U.S. District Court for the Northern District of Illinois, the event brought together three U.S. Magistrate Judges, experienced litigators, and communication specialists. Each of them shared strategies for guiding unrepresented litigants through the settlement process. Attendees received practical tools for case evaluation, client communication, ethical decision-making, and settlement advocacy that benefit both the litigant and the court system.