In a legal landscape where collaboration increasingly intersects with complexity, ethical clarity is both more essential—and more elusive—than ever. This session explores the nuanced ethical dilemmas that arise in civil collaborative practice, particularly in high-stakes fields like partnership disputes, family businesses, and succession law. Grounded in the ABA Model Rules of Professional Conduct, we will examine how collaborative practice wrestles with traditional notions of confidentiality (Rule 1.6), conflicts of interest (Rules 1.7 & 1.9), fiduciary duties, and independent judgment (Rule 2.1). Through real-world scenarios, participants will engage with the ethical tensions that arise when advocacy meets collaborative problem-solving. Whether you’re facilitating generational transitions in family businesses, navigating a business divorce, or addressing asset disposition among beneficiaries, understanding these shifting lines is essential for a sustainable collaborative practice.