Ethical canons expressly require professional fiduciaries make decisions about “best interests” through the prism of their clients’ known ethnic, religious, social, and cultural values. Notably missing from this list is an oft-elided dynamic—many clients and their families are entrenched in dysfunction. How do you recognize and take into consideration the effect of this environment when considering your clients’ best interests? We will discuss real-life examples such as deciding whether to place a client in a professional-care setting rather than allowing care at home by a family member, or, when to pursue litigation to recover misappropriated assets from someone your client wishes to protect. Attendees will discuss how collaboration with counsel is essential to recognize, contextualize, and develop strategies to successfully and gracefully weather these ethical quandaries.