New Zealand was a late starter in the international trend towards employing female prison officers to work in men’s prisons. Even after the first such officer was appointed in 1985, resistance to the idea continued in some quarters. This paper examines the recent history of New Zealand women’s involvement in men’s prisons and the debates that ensued as a result. As will be seen, the fears of male prison officers that inmates would endanger women’s safety proved largely unfounded, and the principal obstacle to women’s integration was not the inmates, but some officers themselves. Nonetheless, certain issues, particularly the risk of females entering into inappropriate relationships with their male charges, remain. The paper discusses the advantages and disadvantages of having women officers working in a front line capacity with male prison inmates, and how some of the problems arising there from have been addressed.