Over 70% of patients suffering from dentofacial deformities mention esthetics as the biggest issue pushing them to look for orthodontic and orthognathic treatment. At present, several pieces of software for computer-aided surgery have been released on the market. This surgical planning software allows surgeons to manipulate digital representations of hard and soft tissue profile tracings and subsequently morph the pretreatment image to produce a treatment simulation. The aims of this study were to investigate and find the difference between two of the most used pieces of digital software in pre-surgical planning for patients affected by dentofacial deformities by using the following parameters: usability, validity, timing, accessibility, efficacy, and predictability of the pre-surgical planning. Analyzing the results obtained from our study, it is correct to define both software tools useful and valid in digital surgical planning for the treatment of patients with dentofacial deformities. Each software has negligible differences in performance that do not in any way affect the success of surgical planning. The IPS software represents a valid alternative to the most popular and tested Dolphin Imaging software, and we are even inclined to evaluate it as better in terms of accuracy, effectiveness, and reliability.