Lichenoid granulomatous dermatitis, also known as giant cell lichenoid dermatitis, represents an uncommon mixed-pattern dermatitis with histopathologic features of interface dermatitis with band-like lymphocytic inflammation of the dermal-epidermal junction, with thinning of the epidermis or lichen planus-like changes, and granulomatous inflammation involving the dermis. Lichenoid granulomatous dermatitis can manifest with a variety of primary lesions and has various clinical associations. We present a challenging clinicopathologic case of lichenoid granulomatous dermatitis in a 58-year-old woman with dramatic cutaneous desquamation in the context of a complex medical history and multiple potential triggers.