A routine cavity preparation of a tooth may lead to opening the pulp chamber. The present study evaluates quantitatively, in real time, for the first time to the best of our knowledge, the drilled cavities during dental procedures. An established noninvasive imaging technique, Optical Coherence Tomography (OCT), is used. The main scope is to prevent accidental openings of the dental pulp chamber. Six teeth with dental cavities have been used in this ex vivo study. The real time assessment of the distances between the bottom of the drilled cavities and the top of the pulp chamber was performed using an own assembled OCT system. The evaluation of the remaining dentin thickness (RDT) allowed for the positioning of the drilling tools in the cavities in relation to the pulp horns. Estimations of the safe and of the critical RDT were made; for the latter, the opening of the pulp chamber becomes unavoidable. Also, by following the fractures that can occur when the extent of the decay is too large, the dentist can decide upon the right therapy to follow, endodontic or conventional filling. The study demonstrates the usefulness of OCT imaging in guiding such evaluations during dental procedures.