Accumulating evidence has shown that the risk of osteoporotic fractures is increased in patients with diabetes mellitus (DM). Thus, DM-induced bone fragility has been recently recognized as a diabetic complication. Because the fracture risk is independent of the reduction in bone mineral density, deterioration of the bone quality may be the main cause of bone fragility. Although its mechanism remains poorly understood, accumulated collagen cross-links of advanced glycation end-products (AGEs) and dysfunctions of osteoblast and osteocyte may be involved. Previous studies have suggested that various diabetes-related factors, such as chronic hyperglycemia, insulin, insulin-like growth factor-I, AGEs, and homocysteine, are associated with the risk of bone fragility caused by impaired bone formation and bone remodeling. Furthermore, several anti-diabetic drugs are known to affect bone metabolism and fracture risk. We herein review the association between DM and fracture risk as well as the mechanism of DM-induced bone fragility based on recent evidence.