Squamous cell carcinoma (SCC) developing in chronic hidradenitis suppurativa (HS) is rare, but failing to recognize the condition may have significant consequences. Dermatologists must be aware of the potential for malignant transformation and should have a low threshold for biopsy when clinical presentation is atypical. Herein we describe a 64-year-old woman with metastatic vulvar SCC that developed within an area of chronic HS. Like SCC associated with other chronic inflammatory disorders (Marjolin's ulcers), mortality is significant. Past reviews have reported death rates above 40% and our most recent update continues to support poor prognoses for these patients.