There is controversy in the literature regarding clinical outcomes of CAD/CAM laminate veneers. The aim of the present study was to assess the impact of different levels of CAD expertise and different software programs on the reliability and reproducibility of digital wax patterns of laminate veneers and single crowns. The present preliminary in vitro study was performed on 10 prepared maxillary central incisors available in dental study models. Of the total, five central incisors were prepared with shoulder finish lines for single crowns, whereas the other five underwent incisal shoulder preparation for laminate veneers. The models were scanned using an intraoral scanner. Four dentists (group DENT) and four CAD dental technicians (group CAD) with expertise in different software programs performed digital diagnostic waxing on all prepared teeth. The resulting digital wax patterns (n = 80) were exported as standard tessellation language (STL) files and superimposed on gold standard digital wax patterns (obtained from the original shape of the teeth before preparations). 3D mesh deviations at the cervical margins as well as distal, mesial, and incisal/palatal surfaces between each STL and the gold standard digital wax patterns were calculated in millimeters using a CAD software program. The mean time required by each operator to perform digital waxing was also recorded. Paired comparisons between groups DENT and CAD as well as between nondental and dental software programs were performed for the crowns and laminate veneers using the Wilcoxon signed-rank and paired t tests (α = 0.05). For group DENT, median deviations for single crowns were 0.15 mm (range: 0.08 to 1.05 mm) and for laminate veneers they were 0.15 mm (range: 0.08 to 0.76 mm). For group CAD, median deviations for single crowns were 0.16 mm (range: 0.09 to 0.73 mm) and for laminate veneers they were 0.10 mm (range: 0.06 to 0.53 mm). The Wilcoxon signed-rank test revealed a statistically significant difference between groups DENT and CAD (P = 0.041) and between the software programs (P = 0.029) for laminate veneers, but not for single crowns (P > 0.05). Furthermore, mean times required for group CAD and for dental software programs were significantly shorter than those for group DENT (P = 0.001) and for nondental software programs (P = 0.001), respectively. Within the limitations of the present study, the findings suggest that CAD expertise and the software program significantly affect digital wax patterns for laminate veneers, but not for single crowns. (Int J Comput Dent 2022;25(4):361-0; doi: 10.3290/j.ijcd.b3555819).