The evolution of digital systems, particularly computer-aided design (CAD) and computer-aided manufacturing (CAM), has made virtual dental modeling a practical component of orthodontic analysis and treatment planning. Prior literature has consistently demonstrated the dependability of digital assessments for measuring anterior teeth and the overall Bolton ratio. The present work aimed to compare mean arch lengths of the upper and lower jaws with a theoretical nickel–titanium wire, while also validating the precision of digital determinations of the anterior and total Bolton coefficients. This retrospective investigation included 138 Caucasian adolescents. Their dental casts were digitized with an extraoral scanner, and all evaluations were performed using Ortho3Shape software. The data recorded included both measured and ideal arch lengths, as well as the anterior and total Bolton indices. Findings revealed that the mean anterior Bolton value aligned with prior reports, supporting the accuracy of digital methods. Consequently, CAD/CAM-generated models can serve as dependable alternatives to plaster ones, simplifying their storage and accessibility. For future research, intraoral scanners (IOS) are recommended, as they require fewer steps and provide higher precision and patient comfort.