The group of middle-aged and elderly women represents the lowest usage rate of information and communication technology (ICT) in Taiwan. This article reports how a social intervention program, the Taiwan Women Up (TWU) program, has helped such group to successfully learn ICT skills with the support of members of nonprofit organizations. The study adopted qualitative research methods and accomplished in-depth interviews with 28 TWU participants to reveal the ICT learning experiences of women learners. The findings show that TWU program enabled middle-aged and elderly women to achieve the goals of supporting their organizations and empowering themselves as more capable ICT users. Learning and sharing ICT experiences with fellow members helped them overcome their frustration; whereas empathetic understanding and support among members provided the main source of encouragement in the learning process. This study showed that NPOs played a critical role in identifying potential learners and sustaining the ICT project successfully.