Adding an evolutionary perspective to anatomy teaching can enrich student learning. One way of introducing evolutionary concepts into a course is by "sneaking it in" by presenting interesting and sometimes entertaining "stories" that add anatomical detail, encourage critical thinking, and illustrate underlying evolutionary history and concepts. The gubernaculum tells one such story; a story that involves the movement of the testes through the fetal abdominal cavity and finally into the scrotum. While it is well understood that the proximate importance of this migration is to guarantee an appropriate thermal environment for sperm production, our understanding of the role of the gubernaculum in anchoring, pulling, and clearing the way for the testes as they descend is only now coming to light. Even less clear is our understanding of the evolutionary forces that ultimately led to such a seemingly vulnerable positioning of the testes. Multiple hypotheses have been proposed, and whether one or more can ultimately explain the seemingly complicated process and curious anatomy, the essential evolutionary test has obviously been met-- it works