The combination of diabetes and peripheral arterial disease (PAD) is challenging in many ways. The characteristic and complex distal distribution of PAD often encountered in patients with diabetes means that bypass surgery in this context is technically challenging. In addition, many of these patients have a burden of serious comorbidities that must be optimized and managed concurrently. While the authors acknowledge that "achieving success" in distal bypass relies on much more than technical expertise, there are some technical aspects that should be considered when planning surgery on these patients. This article outlines some important issues in the treatment pathway of a patient with diabetes and PAD requiring distal bypass surgery--from selection and optimization of the patient (in the context of a multidisciplinary team) and preoperative workup, to the operative strategy planning, technical tips, and nonoperative adjuncts. These considerations, as well as sound knowledge of the underlying disease process, confounding medical factors and awareness of the difficulty in predicting treatment outcomes, should help maximize the chances of success.