This paper focuses on “hermaphrodites” -- that is, individuals who were considered neither simply male nor female -- and the emerging profession of surgery in thirteenth- and fourteenth-century Europe. This era constituted a critical period for the profession of surgery and, as I argue, for long-lived ideas about anatomy’s role in establishing sex. During this period, surgeons made novel claims about their authority to regulate sexual difference by surgically “correcting” the errant anatomies of hermaphrodites. Surgeons’ theories about sex drew upon cultural ideas about gender and anatomy, as well as upon particular notions of what made something “natural.” As this paper shows, technologies of measurement were also finding new prominence within Italian communes just as certain surgeons – who hailed from the same region – were embracing dimensional standards with respect to the human body. I argue that this focus on standardization, which regulated the size and shape of all kinds of materials, mirrored efforts by surgeons to police the body’s proportions and to return it to a “natural” form.