It has been 14 years since Tippins and Wittmann () voiced concern for the overreaching role the expert may play in matters of family law. This article sets their levels of inference within the context of the culture of both law and social science. We examine how inferences are impacted by the relative emphasis child custody experts give to the five stakeholders involved in child custody evaluations (CCEs): courts, lawyers, parents, children, and professional governing bodies. Acculturation of the assessor to law contributes to more egregious inferences, versus the more modest ones Tippins and Wittmann advocated. How evaluators prioritize stakeholders shapes their opinion and methodology. We offer an expanded perspective that views how their levels of inference are manifest in reports, methodology, and recommendations and the influence of the culture of law and the mindset of the clinician. We hope to encourage clinicians to find ways to operationalize clinical humility, assume their proper role, and remain true to their master identity as licensed mental health professionals and their proper sphere of authority.