I am currently leading a digital inclusion project designed to enhance knowledge and comfort with technology and nurture computational thinking among women who were formerly incarcerated and are now seeking to reenter the workforce or adjust to their lives outside the criminal justice system (“women in transition”). While women have become the fastest growing segment of the incarcerated population in state prisons, prison education and reentry programs are not well prepared to respond to this influx. Women in transition rarely have been exposed to solid technology education and they have generally been isolated from the digital world while in prison and consequently face post-incarceration challenges in accessing and using rapidly changing digital technologies. Against this backdrop, we have implemented a technology education program aimed at helping women in transition develop technology skills relevant to job applications and post-incarceration adjustments. Our empirical research examines how different modalities of offering technology education are associated with learning outcomes for women participating in the program and the association of increasing knowledge and skills in digital technologies with self-efficacy, perceived social support, employment, and recidivism. There have been increased calls for reducing recidivism, and this project will provide evidence-based guidance to such efforts. Our project can serve as a template for developing evidence-based technology education for other underserved populations.