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Syphilis, known for its varied presentations, often mimics other conditions, posing diagnostic challenges. Secondary syphilis can rarely manifest as generalised lymphadenopathy, resembling lymphoproliferative disorders. A male in his late 20s presented with appetite loss, bilateral painless lymphadenopathy and hepatosplenomegaly. Initial investigations suggested a lymphoproliferative disorder. Biopsy revealed dermatopathic lymphadenopathy. Detailed sexual history confirmed syphilis, treated with benzathine penicillin, resolving symptoms and lymphadenopathy. Diagnostic delay occurred due to an incomplete sexual history. Syphilis should be considered, even without typical cutaneous manifestations. Similar cases highlight syphilis’s resemblance to malignant lymphoma. Comprehensive patient education and a multidisciplinary approach are vital. Early diagnosis and treatment are essential for optimal outcomes.