In this chapter, the author focuses on her twenty years in HMP Holloway where she began work carrying out an infant observation and left as a psychotherapist working not only with pregnant inmates, mothers and babies but also a wide range of offenders convicted of very violent crimes. The practice of infant observation was developed by the psychoanalyst Ester Bick in 1948 and became part of the training for students studying to become child psychoanalytic child psychotherapists. By the 1970s, infant observation had developed into a course suitable for a larger group of professions. During the initial two years of observing mothers and babies, the general British female population doubled, although the crime rate did not. Nonetheless the crime statistics were staggering. Judges were increasingly handing more custodial sentences to women. The imprisonment of women has far-reaching implications for herself and her family. The impact of imprisonment on female offenders has been well documented in prior research.