Objectives This study aimed to propose a classification system for calcified root canals based on the location of the target point or canal starting point and root canal lumen caliber to facilitate the evaluation of dynamically guided techniques in endodontic treatment. Methods: A retrospective analysis of eight cases with calcified root canals was conducted. Periapical radiographs and cone-beam computed tomography were used to classify cases based on root location and degree of obliteration. Clinical and radiographic outcomes were evaluated. Results: Eight classification types are identified, ranging from non-obliteration and partial obliteration to total obliteration. The location of the root canal lumen varies from the pulp chamber to the apical third of the root. Guided endodontics with dynamic navigation has been demonstrated to be an effective treatment modality in cases of advanced obliteration, thereby substantiating its efficacy in complex scenarios. Conclusions: The proposed classification system provides a framework to understand the complexity of calcified root canals. Guided endodontics with dynamically guided techniques can be valuable in managing these challenging cases, particularly when the root canal lumen is in the apical third. Further studies are needed to validate the classification system and evaluate the long-term outcomes of the different treatment approaches.