The pandemic caused a rapid shift to reliance on technology to meet basic daily needs related to both health and social interaction. As social isolation is known to be a major contributing factor to physiologic decline and psychological morbidity amongst older adults, we sought to study this shift, and conducted a multi-method study including; (1) a cross-sectional telephone survey and in-depth interviews with community dwelling older adults; and (2) interviews with community organizations supporting technology use for older adults. Quantitative data were analysed using descriptive, inferential statistics; qualitative data were analyzed using thematic analysis. Over 800 older adults completed surveys; 41 completed interviews. 26 community organizations shared their perceptions of supporting the rapid shift to virtual technology. Our results emphasize that social pressure plays a core role in adoption of new technology skills. These results are critical to appraise as reliance on digital technologies continues and look to support older adults.