Experience in reviewing, designing, performing field inspections, and installing of geomembrane boots and connections to structures has revealed a widely diverse practice of standards and approaches. The execution of these details is very much an art in workmanship, and depends a great deal on the experience and understanding of the installer. There is very little guidance in the literature regarding the fine points of specifying and installing these critical details. The typical manufacturers’ details and guidelines are not much more than concepts that have been repeated for two decades. Thus, there is a big difference between what we assume and expect versus what is constructed in terms of leak resistance of geomembrane penetrations and attachments to structures. The goal of this paper is to touch upon some of the detailed and critical aspects that should be addressed when specifying and constructing geomembrane seals around penetrating pipes (referred to as “boots”) and attachments to structures.