Background <p>Kissing molars (KMs) is a rare dental impaction where the occlusal surfaces of two molars are in contact within a shared dental follicle. While typically non-pathogenic, it may induce cystic changes which ultimately determine the appropriate management and overall prognosis.</p> Case presentation <p>In this report, we present a case of kissing second and third left mandibular molars identified on routine examination. Intraoral Radiography showed an associated unilocular radiolucency engulfing the crowns of the impacted teeth. Cone-beam CT showed no involvement of the inferior alveolar nerve or perforation of alveolar bone. Surgical extraction of both teeth alongside enucleation of the lesion was performed. Histopathological analysis confirmed the diagnosis of a dentigerous cyst.</p> Conclusion <p>This case emphasizes the importance of routine radiographic assessment for the early detection of oral pathologies along with selection of the suitable treatment modality. Image-guided surgical removal of both teeth and cyst was individualized for the patient to reduce risk of complications.</p>