It is since the beginning of the so-called 'digital revolution' in the 1950s that technological tools have been developed to simplify and optimise traditional, time-consuming, and laborious anamnestic collection for many physicians. In recent years, more and more sophisticated 'automated' anamnestic collection systems have been developed, to the extent that they can actually enter daily clinical practice. This article not only provides a historical overview of the evolution of such tools, but also explores the ethical and medico-legal implications of the transition from traditional to digital anamnesis, including the protection of data confidentiality, the preservation of the communicative effectiveness of the doctor-patient dialogue and the safety of care in patients with poor digital and health literacy.