(1) Background: Nonsurgical endodontic retreatment procedures have a high potential for success when case selection guidelines are followed, advanced technologies and techniques are employed, and the best materials are used. The aim of the study is to demonstrate that conservative orthograde endodontic retreatment represents a safe management solution for cases of primary endodontic treatment failure. (2) Methods: The study was undertaken between 2022 and 2024, involving a cohort comprising 30 patients of diverse gender and age demographics who sought treatment at the Endodontics Clinic from the University of Medicine and Pharmacy from Craiova and received an endodontic retreatment. The study included three groups: one with inadequate coronal and root canal obturation, another  with clinical symptoms, and the third with radiological signs of apical periodontitis. (3) Results: Orthograde endodontic retreatment is a conservative method of keeping the tooth on the arch, but it needs technology to establish the diagnosis and to perform the treatment itself. (4) Conclusions: In cases of primary orthograde endodontic treatment failure, modern endodontic management emphasizes repeating a conservative approach, reserving surgical endodontic intervention only as a last resort.