Recent reports in the literature demonstrate the influence that digital dentistry is having on the preclinical training of dental students. However, none of these articles have discussed the use of PrepCheck (Sirona Dental Systems) in the evaluation of preparation taper in a preclinical environment. The present study compared the subjective grading of student tooth preparations by experienced, well-calibrated faculty with objective digital grading of the same preparations by means of the PrepCheck software. Sixty-nine sophomore dental student preparations were first subjectively graded by their dental instructors, and then the preparations were evaluated by the PrepCheck software. Neither the students nor the instructors were aware that the second PrepCheck evaluation was going to occur. The statistically significant results of this study conclude that the subjective instructor grades were inflated compared with the digital PrepCheck grades. The inflated grading by the instructors may give students a sense that their progress is better than it actually is. The objective, exact nature of the PrepCheck evaluation gives students immediate feedback regarding their preclinical preparations. Although taper was the only parameter examined in this study, PrepCheck allows the operator to examine many other features of a student's preparation. Also made evident in this study is the fact that the present standard for preparation taper is unattainable in a preclinical environment and needs to be readjusted to a wider, attainable range. Keywords: education technology, digital grading, PrepCheck, preparation taper