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This is a case of swelling originating from dens invaginatus associated with lateral incisor, misdiagnosed as a globulomaxillary cyst. The initial diagnosis of globulomaxillary cyst was made solely from radiographs by observing a reverse pear-shaped radiolucency between the lateral incisor and cuspid. The results following pulp testing and Cone Beam Computed Tomography (CBCT) evaluation revealed the endodontic origin of the lesion, which entailed the treatment carried out by surgical enucleation and apicoectomy. This also details the clinical and diagnostic dilemma as well as conflicts associated with the diagnosis and management of the cystic lesion.