Chapter 5 examines what happened to women who did not conform, the troublemakers and heretics who refused to adhere to the expectations of their faith and their societies. This chapter offers a case study of Ann Hibbens, who exemplifies the dangers to women who transgressed gendered boundaries. The wife of a wealthy and well-regarded man, Hibbens faced censure charges when she disputed the work and fees of a carpenter she hired. While negotiating such work fell within the boundaries of wifely duties, challenging a man in business did not. In her censure process, Ann did not adhere to the expectations for a female sinner and was resolute that she was right and refused to submit to the authority of men. Any deviance or defiance of the social norms branded women as suspect, and Ann’s determination to spar with men made her very dangerous. When her husband died, leaving her unprotected, she went from a troublesome woman to a witch. The costs were high for such women in early New England.