Odontogenic cysts commonly encountered in dental practice are the radicular cysts and dentigerous cysts. Apart from the developmental origin of dentigerous cysts, an inflammatory origin has also been suggested. It has been reported that inflammation progressing from the root apex of the deciduous tooth brings about development of the dentigerous cyst around the unerupted permanent tooth. The aim of the present article is to report 4 additional cases of dentigerous cyst believed to be of inflammatory origin and to highlight the diagnostic dilemma in segregating both the entities. The 4 cases were of patients with a mixed dentition with the pathology related to the deciduous tooth present. Radiographically, pericoronal radiolucency was seen attached at the cementoenamel junction of impacted tooth and in continuation with lamina dura of deciduous tooth. Microscopically, the cystic cavity was lined by reduced enamel epithelium like lining, which was hyperplastic to anastomosing in areas in few cases. This study proposes the predicament in accurately diagnosing such cases.