This chapter explores inflammatory lymphadenopathies with skin involvement, a diagnostic challenge due to their overlap with malignancies and other inflammatory diseases with secondary lymph node enlargement. It covers key conditions, including Kikuchi disease, Kimura disease, Castleman disease, and IgG4-related disease, each with unique clinical and histopathological features. Kikuchi disease is highlighted for its benign, self-limited course, while Kimura disease and Castleman disease exhibit chronic inflammatory or paraneoplastic skin changes. The chapter emphasizes the importance of detailed diagnostic evaluations, such as lymph node biopsy and imaging, to distinguish these reactive conditions from malignant processes. Treatment strategies vary from observation in benign, self-resolving conditions to immunosuppressive therapies in more aggressive inflammatory diseases.