Skeletal fragility has been recognized as an important feature of diabetes mellitus type 1 (T1D) and type 2 (T2D). While patients with DM1 typically display low bone mineral density (BMD) and concomitant increases in fracture risk, T2D bone disease is more complex and less understood. Although BMD is often normal or even slightly elevated, the risk of fragility fractures is disproportionally high. Alterations in bone quality (i.e., bone microstructure and matrix properties) have been reported by independent groups of researchers. Cortical porosity and the deposition of advanced glycation end-products appear to play key roles. Paired with low bone turnover, another distinct feature of T2D bone disease, secondary complications (including nephropathy, neuropathy, and angiopathy) are adding up to form a complex entity distinct from postmenopausal and age-related osteoporosis. This article offers an overview of current concepts in pathophysiology, clinical features, and imaging features of diabetic bone disease.