Background: Upper esophageal perforations are life-threatening conditions associated with a high risk of mediastinitis, sepsis, and multiorgan failure. Standard management often requires extensive surgical intervention, which carries substantial morbidity. Methods: We report the case of a 56-year-old male with an iatrogenic cervical esophageal perforation complicated by cervicomediastinal abscess formation. Due to anatomical constraints preventing standard endoluminal approaches, a hybrid organ-preserving strategy was employed, consisting of surgical drainage combined with an externally adapted vacuum-assisted closure (VAC) system applied adjacent to the esophageal defect. Results: The patient demonstrated progressive clinical improvement without the need for esophageal diversion or major reconstructive surgery. Inflammatory markers were monitored serially and showed a downward trend, serving as adjunctive indicators of treatment response. The esophageal defect healed successfully, was confirmed radiologically, and no treatment-related complications were observed. Conclusions: This case suggests that externally adapted VAC therapy may represent a potential organ-preserving option in selected patients with complex cervical esophageal perforations when conventional techniques are not feasible. Further studies are required to validate this approach.