Synchronous lung and esophageal carcinomas are rare (incidence 0.54–3.2%) and carry high postoperative complication risk. This case series of three patients demonstrates that curative resection with lymph node dissection is the optimal treatment, but decisions must be individualized via multidisciplinary tumor board evaluation. Two-stage surgery and careful patient selection can mitigate complications, though even optimal candidates may experience unforeseen adverse events.