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Emphysematous osteomyelitis is a rare condition caused by gas-producing bacteria in the bone and may be visualized by the presence of intraosseous gas on imaging. We report three cases of emphysematous osteomyelitis. The first case is an 80-year-old with acute myeloid leukemia with emphysematous osteomyelitis of the sacrum, right iliac bone, and multiple vertebrae and ribs. Blood cultures grew Enterococcus faecium and Clostridium spp. The second case is a 45-year-old man with diabetes mellitus with emphysematous osteomyelitis of the proximal left tibia with blood cultures positive for Proteus mirabilis and Clostridium perfringens. The final case is a 57-year-old male with diabetes mellitus who presents with emphysematous osteomyelitis of the left fifth metatarsal head. Wound cultures were positive for Klebsiella pneumoniae and Proteus mirabilis. Emphysematous osteomyelitis is associated with significant morbidity and mortality, and so an accurate and quick diagnosis is important for the radiologist to make.