Preauricular sinuses are congenital anomalies arising from the incomplete fusion of hillocks of His of the first and second branchial arches. Surgery is warranted when there is recurrent infection or abscess formation. However, the presence of scarring and skin thinning could result in large tissue defects after complete excision. In such cases, meticulous preoperative planning with regard to the reconstruction technique is imperative. We describe the clinical presentation, surgical technique, and postoperative outcomes of such a case in a young toddler, with a focus on the rationale behind the chosen management strategy. By sharing our experience, we aim to contribute to the existing literature on the management of complicated preauricular sinuses and provide insights that may guide clinicians facing similar challenges.