Background: Traditionally, guidelines issued by medical societies have provided a standard of care for the treatment of disease processes, establishing clear pathways, and limiting litigation. A major ethical dilemma may occur when an update in guidelines may lead to an instant change in the standard of care. Methods: We present a hypothetical clinical scenario of esophagogastric obstruction outflow obstruction (EGJOO) where guidelines were changed, and we asked the opinion of experts in different areas—surgeons, ethicists, and lawyers. Results: Each group of experts presented their opinion on ethical issues relevant to the clinical case. Conclusions: The clinical case presented and the guidelines for the treatment of primary esophageal motility disorders based on the Chicago classification 4.0, represent a current issue that the world of medicine has to face. While guidelines are usually particularly useful for practitioners, they must be based on irrevocable principles. They must be the result of a rigorous scientific analysis of available data by a group of real experts, and opinions should be avoided if not based on evidence. The level of evidence should be clearly stated, stressing the weakness of some recommendations when present. Conflicts of interest of the Authors of the guidelines should be not only declared, but carefully analyzed in order to avoid biases. Finally, radical changes in a short period of time should be avoided as they expose the practitioners to poor outcomes and litigation.