Dens invaginatus is a common malformation of maxillary lateral incisors with varying anatomical features that impose challenges to diagnosis and treatment. It is considered a real clinical entity which, even if the tooth is clinically healthy, it can cause pulpal damages that can progress silently and lead to necrosis and its complications. The aim of this article is to expose a clinical case of patient with two types of dental invaginations; I and II incidentally discovered during a routine radiological examination, affecting the two permanent maxillary lateral incisors which are clinically healthy, and which required endodontic treatment following pulpal damages. The focus will be on the description of the clinical and radiological characteristics of this abnormality, the difficulties and the strategies employed to manage this clinical condition.