Background: Our country struggled with a plethora of mucormycosis cases during the second wave of coronavirus disease 2019 (COVID-19). The dental community was burdened with different maxillectomy defects in which bilateral maxillectomy cases posed a significant challenge for rehabilitation. Rehabilitating a patient after maxillectomy with conventional obturator prosthesis to close oronasal communication can be an effective way of restoring speech, deglutition, and mastication, and preventing nasal regurgitation. But the main problem is the retention of an obturator in large defects, and there is sparse literature pertaining to the management of bilateral maxillectomy cases in the surgical obturation phase. Purpose: The purpose of this case was to rehabilitate patients with a bilateral maxillectomy defect in the healing phase with an obturator prosthesis retained using extraoral aid where intraoral retention is not possible. Technique: Two different modification techniques in the extraoral retentive method were tried here to overcome difficulties encountered during the rehabilitation of such cases, with special emphasis on augmenting patient comfort. The customized headgear facebow assembly was used for extraoral retention. In the first case, an orthodontic was used to retain the prosthesis to the customized headgear or extraoral elastic straps through orthodontic elastics. The orthodontic facebow has two parts inner and outer bow. The inner bow was attached to the obturator at the level of the occlusion plane by fabricating bilateral posterior acrylic pillars so that the outer bow passes along the commissures of the mouth, but there was the problem of lip trap and feeding difficulties due to the horizontal connecting bar. To overcome these problems, in the second case, the facebow was customized using a 19 gauge orthodontic wire to eliminate horizontal component. Conclusion: The obturator with extraoral retention in the healing phase is a viable retentive aid in patients with extensive maxillary defects, and it was found that the patient was more comfortable with a customized facebow-retained obturator.