This interactive workshop explores how balancing support for colleagues and medico-legal responsibilities intersect in the medical profession. It invites participants to examine real-world stories and scenarios that reveal tensions between compassionate colleague support, duty of care, confidentiality, and legal obligations. Through facilitated discussion, case vignettes, and practical tools, attendees will learn strategies to recognise when to and how to have a supportive mental health conversation, engage appropriate escalation pathways (if required) while maintaining relational trust. The session emphasises trauma-informed communication, boundaries, and respectful approaches, and offers clear guidance on when to seek legal or clinical oversight.