We present a 56-year-old man with known diabetes mellitus and a 10-year history of hidradenitis suppurativa (HS) and highlight, through MR imaging findings, the relentless natural progression of the disease, characterized by recurrent exacerbations of abscesses and fistulae and complications of perianal fistulae and sacral osteomyelitis. We also demonstrate the appearance of this condition on PET-CT with F-18 FDG, which was performed for staging after postexcision tissue specimen revealed well-differentiated squamous cell carcinoma. The association of arthritis and possible dactylitis was also manifested in our patient. Discussion of HS in the radiology literature is limited and, to our knowledge, there has been no case report describing these imaging findings in the same patient.