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Introduction: Lichen planopilaris (LPP) is a primary lymphocytic cicatricial alopecia that represents a form of follicular lichen planus. Case Presentation: We describe a case of coexisting diffuse LPP and female pattern hair loss masquerading as diffuse alopecia areata in a 32-year-old female. Discussion: In complex cases such as this, dermoscopy-guided vertical and horizontal biopsies from androgen sensitive and insensitive areas are helpful in increasing diagnostic yield. Prompt initiation of treatment is key to halting disease progression. Long-term follow-up is important as resolution of clinical signs does not always correlate with the absence of disease progression.