Cephalometry is a crucial examination in orthodontic diagnostics and during the planning of orthognathic surgical procedures. The objective of this article was to compare cephalometric measurements conducted by different specialists and systems tailored for such measurements, as well as to evaluate the capabilities of artificial intelligence in this field. In January 2024, we conducted electronic searches in the PubMed, Scopus, and Web of Science (WoS) databases. In the Scopus database, the results were refined to titles, abstracts, and keywords, while in PubMed, they were narrowed down to titles and abstracts. In WoS, the results were refined only to abstracts. The search criteria were based on the following terms: (cephalometric) AND (analysis) AND (discrepancy) AND ((orthodontic) OR (radiologist)). A total of 263 articles were identified, of which 17 met the criteria and were incorporated into the review. The review allowed us to conclude that the accuracy of cephalometric measurements relied on the expertise of the operator—specialists with more experience exhibited greater precision compared to novices or individuals not specialized in orthodontics. Cephalometric measurement computer programs yielded outcomes that streamlined work processes, minimized human errors, and enhanced precision. A novel aspect involved the application of artificial intelligence, which also demonstrated high precision and a substantial reduction in working time, although its utilization still necessitates further enhancements. Further research was required to address these limitations and to optimize the incorporation of technology in orthodontic and orthognathic surgery practices.