This chapter treats the lives of those boys whose family and inheritance systems failed to provide the sort of economic and social support that Ser Andrea Nacchianti, however grudgingly, provided for the boys and girls in his kinship network who fell outside the categories of the statutory inheritance grid. Although much recent scholarship has focused on the problems this created for women, only a handful of scholars has explored the social consequences of homelessness for boys. In particular, Ottavia Niccoli has juxtaposed the perceptions and realities of links between undisciplined boys and violent criminality, as well as noting their vulnerability to exploitation. For the fifteenth century, Michael Rocke has analyzed the social boundaries of cross-generational homoerotic bonds as a foundation of patronage and male sociability. Konrad Eisenbichler's more chronologically extended study of a youth confraternity across the entire early modern period has brought the techniques of confraternal discipline into much sharper focus. More recently, Ilaria Taddei has chronicled the lives and childhood careers of boys in various Florentine youth confraternities, and Nicholas Terpstra has done the same for boys in orphanages in Florence and Bologna.