Unusual root canal configurations in maxillary first molars (MFMs) continue to challenge diagnosis and treatment. Distobuccal (DB) canal variations are uncommon and easily missed. A 34-year-old male presented with persistent pain in the upper left first molar (FDI tooth 26) after emergency access at a private clinic. The tooth diagnosis was pulp previously initiated with symptomatic apical periodontitis. Non-surgical root canal treatment was performed. Under magnification, five canals were identified: MB1, MB2, P, and two DB canals (DB1, DB2). The DB canals were separate coronally and converged at the mid-root, continuing to a single apical foramen. Standard rotary shaping with NaOCl/EDTA irrigation and cold lateral condensation were performed. Clinical and radiographic observations confirmed a Vertucci type II configuration of the DB root. Two DB canals that merge mid-root can occur in MFMs. Thorough knowledge of dental anatomy, vigilant inspection under magnification, judicious troughing, and multiple angled radiographs help prevent missed anatomy.