In developed countries, clinical manifestation of carious lesions is changing: instead of dentists being confronted with wide-open cavities, more and more hidden caries are seen. For a long time, the focus of the research community was on finding a method for the detection of carious lesions without the need for radiographs. The research on Digital Imaging Fiber-Optic Transillumination (DIFOTI) has been an active domain. The scope of the present article is to describe a novel technology for caries diagnostics based on Near Infrared Digital Imaging Transillumination (NIDIT), and to give first examples of its clinical indications. In addition, the coupling of NIDIT with a head-mounted retinal image display (RID) to improve clinical workflow is presented. The novel NIDIT technology was shown to be useful as a diagnostic tool in several indications, including mainly the detection of proximal caries and, less importantly, for occlusal caries, fissures, and secondary decay around amalgam and composite restorations. The coupling of this technology with a head-mounted retinal image system allows for its very efficient implementation into daily practice.