This article gathers diverse attachment specialists in a far reaching conversation about the utility of attachment assessment and theory for complex family law decision making, and reflections on the thorny question, “If I were the judge . . .?” Inge Bretherton, Professor Emerita, Developmental Psychology at Wisconsin University, is one of a few attachment researchers in the Bowlby/Ainsworth tradition to have completed studies in the divorce field. Seligman, a psychoanalyst and clinical psychologist, Solomon, a clinical psychologist and researcher, and Crowell, professor of psychiatry and psychology, take on some large controversies, and offer well over 100 years combined experience of applying attachment knowledge in complex family matters.