Necrobiosis lipoidica diabeticorum (NLD) is a rare, chronic disease characterised by clinical features of yellow-brown, atrophic, telangiectatic plaques usually located on the lower extremities, and pathological features of collagen necrobiosis and inflammation in the dermis. Most cases are seen in patients with diabetes mellitus, particularly type 1 diabetes, and in patients without diabetes most have evidence of abnormal glucose tolerance or report a family history of autoimmune disease . We describe three patients with NLD and type 1 diabetes: (1) a 24-year-old female with extensive erythematous plaques responsive to laser therapy, (2) a 24-year-old female with recalcitrant localised disease despite prolonged treatment with multiple therapeutic agents including topical and systemic steroids, calcineurin inhibitors, and hydroxychloroquine, and (3) a 22-year-old female who reported longstanding brown-to-red papules localised on the shins, with biopsy demonstrating classical features of NLD; she is yet to start treatment. A common theme to all three cases is the late identification and delay in reaching the correct diagnosis. Hence, we discuss the important clinical characteristics and features and discuss the management and prognostic implications for this distinctive cutaneous entity. Whilst most cases will remain relatively asymptomatic, others progress to a more debilitating illness with pruritus, dysesthesia, and pain. Pain is often intense in the presence of ulcerated plaques, the latter being an unfortunately morbid complication of NLD. The clinicopathological diagnosis of NLD requires the integration of both the clinical and histopathological findings. NLD has proved a challenging condition to treat, and despite the numerous therapeutic modalities available, there remains no established standard regimen of care. We provide an overview of current management strategies available for NLD.