Anastomotic leaks after gastrointestinal surgery have an important impact on surgical outcomes because of the high morbidity and mortality rates. Multiple treatment options exist requiring an individualized patient-tailored treatment plan after multidisciplinary discussion. Endoscopic vacuum therapy (EVT) is a novel treatment option that is nowadays recognized as an effective and useful endoscopic approach to treat leaks or perforations in both the upper and lower gastrointestinal tract. EVT has a very good safety profile. However, it is a time-consuming endeavour requiring engagement from the endoscopist and understanding from the patient. To the unexperienced, the EVT technique may be prone to several hurdles which may deter endoscopists from using it and depriving patients from a potentially life-saving therapeutic option. The current review highlights the possible difficulties of the EVT procedure and aims to provide some practical solutions to facilitate its use in daily clinical practice. Personal tips and tricks are shared to overcome the pre-, intra- and post-procedural hurdles. An instructive video of the procedure helps to illustrate the technique of EVT.