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Hypertrophic scars are fibroproliferative lesions that form at the site of a wound due to excessive collagen deposition during the healing process. These scars remain confined to the original wound boundaries and may improve over time. Their formation is a complex process influenced by multiple factors, including wound depth and location, tension on the healing skin, genetic predisposition, and the inflammatory response. Abnormal regulation of fibroblasts and prolonged inflammation lead to excessive deposition of type III collagen (the final tensile collagen), resulting in a thickened, raised scar. Mechanical stress at the wound site, such as in areas of frequent movement (e.g., the abdomen), may also contribute to the development of exaggerated scarring. Additionally, delayed wound healing or infection, as seen in some postoperative cases, increases the risk of hypertrophic scar formation. Management often requires a multimodal approach involving pressure therapy, topical agents, corticosteroid injections, or surgical revision, depending on symptom severity. We present the case of a 46-year-old man with a complicated postoperative course who developed a symptomatic hypertrophic scar and a subsequent incisional hernia following laparoscopic cholecystectomy. Surgical excision of the hypertrophic scar with concurrent hernia repair and intralesional triamcinolone injection was performed; however, recurrent hypertrophic scarring developed postoperatively. Histopathologic examination confirmed the presence of dense collagen bundles, consistent with a hypertrophic scar. Although the patient achieved partial symptom relief with topical Contractubex<sup>®</sup>, he continued to experience tenderness and erythema at follow-up. This case outlines the complex interplay among infection, mechanical stress, and aberrant wound healing in the development of hypertrophic scars and incisional hernias. It further highlights the need for early recognition and a multimodal, individualized management strategy to optimize functional and cosmetic outcomes.