The healing of gastrointestinal anastomoses is a complex biological process influenced by numerous factors. Various strategies to support healing and prevent anastomotic leakage (AL) exist, encompassing preoperative, intraoperative and postoperative measures. Preoperative interventions aim to optimize the patient and the tissue environment, particularly the gut microbiome. Intraoperative measures are technical in nature and include the choice of surgical access, the anastomotic technique and anastomotic reinforcement. Various procedures of the intraoperative diagnostics enable identification of such anastomoses requiring additional protective measures. Recently, indocyanine green (ICG) fluoroscopy has become established for evaluation of tissue perfusion, while newer techniques such as spectral microscopy offer promising possibilities. Postoperative diagnostic methods aim to identify potential AL as early as possible to enable initiation of therapeutic steps even before the onset of symptoms. These procedures range from various imaging techniques to innovative bioresorbable, pH-sensitive implants for early AL detection. Due to the multifactorial genesis of AL and the diverse technical possibilities, no single method will become established for prevention of AL. Instead, a combination of measures will ultimately lead to optimal anastomotic healing. The use of artificial intelligence and analyses based on the data promises a better interpretation of the vast amount of data and therefore to be able to provide general recommendations.