Health and mental health interventions, such as psychotherapy and exercise programs, delivered via information and communication technology (ICT) may improve service access. However, adjustment among older people and in synchronous group interventions is more challenging. Technology affordance concerns the possibilities engendered by technology for various users and purposes and can help understand challenges in ICT-delivered groups and identify possible solutions. Adopting a multiple triangulation approach, we observed ICT-delivered groups of acceptance and commitment therapy and exercise for older people with depressive symptoms, conducted focus groups with older people who had received group psychotherapy with or without an exercise component, and obtained clinical notes from interventionists. We conducted a thematic analysis of the observation notes, focus group transcriptions, and clinical notes. Four focus groups were conducted with 22 participants (mean age = 72.6 years, standard deviation = 7.2, 86% female). We identified 3 challenges: (1) seeing-be seen dilemma, (2) speaking-hearing dilemma, and (3) blurred therapy-home boundary, and 2 solutions: (1) maneuvering layouts and collaborative tools, and (2) cross-platform mediated strategies. Participants struggled to observe the interventionist while simultaneously demonstrating their posture in front of a camera. Remaining silent and moderated turn-taking allowed for clearer hearing but limited interactions. Interruptions from the background environment and intersections of family living spaces disrupted audio-visual communication and jeopardized the sense of security. As a solution, interventionists maneuvered layouts and collaborative tools on teleconferencing applications to achieve intervention goals and provided support through different media. The identified challenges and potential solutions can be understood from interactivity, portability, temporality, persistence, and multimediality. Technology affordance can guide ICT-delivered group design by matching the affordance of various technologies and communication media with the characteristics of the intervention and users to enhance efficacy and avoid an unnecessary digital divide.