Despite progress in the last decades, pancreaticoduodenectomy is still associated with high morbidity and mortality, especially in cases where pancreatic anastomosis presents higher complexity. As minimally invasive pancreaticoduodenectomy establishes itself as a safe alternative to traditional open surgery with remarkable benefits, surgeons might face challenges such as mastering complex anastomoses. This chapter offers a guide to managing complex PA in both approaches and offers tips and tricks focused on preoperative, intraoperative, and reintervention strategies. While the recommendations provided are applicable to open and minimally invasive settings, we hope these recommendations will encourage surgeons who would otherwise have only considered open surgery to also contemplate laparoscopic or robotic approaches as safe and plausible alternatives.