The Center for Women in Transition was created in 1997 after four women volunteering in prison ministry noticed a cycle of recidivism. The volunteers met with incarcerated women to identify root causes of their returns to incarceration and discovered the following challenges: lack of safe, affordable housing; lack of access to services such as substance use treatment, job placement, food, and transportation assistance; and lack of positive social support. The system was structured for failure. The Center was formed specifically to ​address these challenges.

Formed on a belief in restorative practices, the Center initially offered mentoring partnerships. It has since expanded to offer comprehensive wrap-around services, including supportive housing; case management; life skills education; behavioral health services; peer support services; provision of basic necessities including food, transportation, and clothing; vocational services; and mentor partnerships. Since 1997, the agency has served over 2,300 women.

In 2022 the Center changed its name to Keyway Center for Diversion and Reentry, which better expresses the work ​being done for justice-involved individuals. The mission and services remain the same.