Older adults living in residential care often experience challenges in sustaining meaningful social relationships, which can result in compromised health and well-being. Online social networking has the potential to mitigate this problem, but few studies have investigated its implementation and its effectiveness in maintaining or enhancing well-being. This pilot study used a cluster-randomized pre–post design to examine the feasibility of implementing a 12-week group-based technology-training intervention for older adults (n = 48) living in residential care by exploring how cognitive health, mental health, and confidence in technology were impacted. Analysis of variance revealed significant increases in life satisfaction, positive attitudes toward computer use, and self-perceived competence among participants who received the intervention, but increased depressive symptoms for the control group. These findings suggest that, despite challenges in implementing the intervention in residential care, group-based technology training may enhance confidence among older adults while maintaining or enhancing mental health.