This article investigates an intergenerational information and communications technology (ICT) program that seeks expressly to enhance children’s civic participation by placing them in mutually educational encounters with seniors. Applying Devine’s model of the interrelationship among structure, power, and agency, it problematizes this goal by analyzing the dialectics of the power relations between seniors and children who maintain a technology-driven relationship. The data were gathered via qualitative participant-observation in two elementary schools. The results reveal clashing implications for children’s empowerment as computer "teachers" and their experiencing of agency. Implementation of Devine’s theoretical model sheds light on the meanings of the stereotyped terms "digital natives" and "digital immigrants," as well as on the a-stereotyped senior’s identity as "digital consumers." The conclusions suggest that the technological gap may not be definitive in confirming young people’s supremacy in the generational hierarchy, signaling the need for caution in handling this gap via civic empowerment in an educational setting.