Pre-prison experiences and environmental influences were examined to determine the effects of institutional misconduct and symptoms of depression related to adjustment in Taiwan’s women’s prisons. Using self-reported survey data derived from 883 Taiwanese female inmates, the findings suggest that pre-prison victimization, imprisonment stress, and social support from family members all had statistically significant effects on adjustment to life in prison. Although deviance prior to prison was highly related to institutional misconduct, reported illnesses also significantly increased the level of symptoms associated with depression. Lower levels of institutional misconduct were reported by women who committed drug offenses compared with their counterparts who committed violent offenses. The article concludes with insights from a comparative perspective and public policy implications.