<p>Hospitals, health centres and asylum buildings fall within the sphere of so-called health architecture, places oriented towards health promotion and prevention. A solid evolutionary process characterises all structures that accommodate health-related functions owing to the constantly changing needs of society, methods of treatment/prevention and complex scientific and technological advancements. Architectural health structures need to be kept modern and up to date, and heritage buildings are generally considered unsuitable. The evolutionary process has often radically changed the relationship between hospitals and historic structures or hospitals and the city. Initially located within the historic urban fabric, health structures were shifted outside of it in the 20th century into new modern complexes in suburban areas. The case of the Ca’ Granda Ospedale Maggiore Policlinico in Milan is particularly emblematic of the inwards/outwards hospital relocation phenomena that occurred around Italy during the 20th century, and it can compellingly trigger a debate over the conservation/innovation challenges faced by the built heritage of health.</p>