Background: Regarding the new dental licensing regulations in Germany (AOZ), this study evaluated the effectiveness of two different digital tooth preparation validation systems in comparison to traditional faculty feedback. Methods: Participants were randomly divided into groups: Faculty Feedback (FF: n = 33), PrepCheck® (PC: n = 32) and Dental Teacher™ (n = 32). Students had the task to prepare tooth 16 for a retentive full-cast crown. Preparations could be repeated as often as desired. Feedback was provided either by faculty staff or by digital validation systems only. Exams were conducted and graded by two independent and experienced examiners. A survey was performed to evaluate the assessment concepts. Results: No statistical difference in examination performance between groups could be observed. Nevertheless, the survey showed participants preferred consulting the faculty staff rather than the digital validation systems. Students preferred practising with DT rather than with PC. Conclusions: Although both classical and digital methods showed comparable results regarding the preparation examination performance, direct feedback by the faculty staff is still appreciated by the students. A combination of both methods is mandatory since demonstration and advice by the teacher is needed. However, digital tooth preparation validation systems are predestined for free practice sessions, providing self-assessment.