Background: Cervical esophageal reconstruction is vital to improve the quality of life in cancer surgery patients. Microsurgery is crucial in providing vascularized tissue for defect repair, particularly in secondary cases with a higher risk of failure due to larger defects and damage from previous surgery and radiotherapy. The purpose of this study was to describe the clinical characteristics of a series of patients who underwent secondary repair of esophageal defects and provide practical information for the management and treatment of such cases based on the authors’ experience and the literature review. Methods: We retrospectively reviewed the electronic medical records of the Plastic Surgery Clinic at the University of Trieste to identify cases of patients who underwent secondary esophageal microsurgical reconstructions following oncological surgery. Patient demographics, the etiology of esophageal defects, previous surgical history, and preoperative assessments were collected from medical records. Surgical techniques utilized for reconstruction, such as pedicled flaps or free tissue transfers, were documented along with intraoperative information. Postoperative outcomes, including complications, graft viability, and functional outcomes, were evaluated during follow-up. Results: We treated 13 cases of secondary esophageal reconstructions between 2011 and 2022. Most commonly, Antero-Lateral Thigh (ALT) flaps were used in 10 cases, while 2 cases employed a radial forearm flap (RFF), and 1 case employed a chimeric parascapular flap. No flap failures occurred during a median 50-month follow-up. One ALT flap patient experienced postop stricture but maintained swallowing ability. A single tracheoesophageal fistula occurred in an RFF patient with a history of radiotherapy and complete lymph node dissection. Conclusions: Cervical esophageal reconstruction significantly impacts patients’ quality of life by restoring oral feeding and phonation. When local flaps fall short, microsurgical reconstruction with intestinal flaps is valuable but is burdened by limitations. For challenging secondary cases, ALT or RFF flaps emerge as safer options due to their robust pedicles, yielding low complication rates and positive functional outcomes.