Runaway slave advertisements are a staple of African and African American Studies. For well over a century, they have provided scholars from many different disciplines a rich resource to examine slavery. In addition to recording slaves dogged determination to be free, their persistent efforts to preserve family ties, and their astute awareness of the politics of their day, advertisements for fugitive slaves include complex stories that reflect varied nuances of the past. It is those nuances that represent the focus of this article that explores bondage in colonial New England.