Foot problems are common causes of disability in diabetic patients with as many as 25% expected to develop severe foot or leg problems during their lifetimes. Although skin ulceration is the most frequent problem, bones may also be involved in two different clinical conditions: osteomyelitis and Charcot osteoarthropathy. Osteomyelitis causes complications in up to one third of diabetic foot infections and is due to direct contamination from a soft-tissue ulcer. Osteoarthropathy Charcot foot is a chronic and progressive disease of the bone and joints. Both osteomyelitis and Charcot joint are conditions with an increased risk of lower limb amputation, both may have a successful outcome when recognized and treated in the early stages. The major diagnostic difficulty is in distinguishing bone infection (osteomyelitis) from non-infectious neuropathic bony disorders as in osteoarthropathy Charcot foot. An additional difficulty is found when a bone infection superimposes a Charcot osteopathy. This condition, which can be clinically suspected when foot ulceration appears in Charcot foot, needs to be diagnosed because it implies a different therapeutic strategy. This article aims to summarize both these two clinical conditions and give indications to make a timely and correct diagnosis.