The phenomenon of ageism is learned at an early age and has lifelong implications on technology design, adoption, and fluency. There is ample evidence supporting this statement. This chapter shares related findings from two American studies; a 2021 study sought to understand the experiences of older adults (those 65 years and older) using everyday information and communications technology (ICT). The second study, conducted in 2022 and 2023, gleaned insights from individuals 17–85 years who provided older adults with hands-on technology instruction. As longevity increases and technological solutions increasingly replace those that humans previously handled, it is evident that those who do not have the tools and the skills to use technology are being left behind. While there is general agreement that a problem exists, the topic of older adults and their digital exclusion seems to be deprioritized by the media, policymakers, corporate leaders, and technology manufacturers—the groups best positioned to increase awareness and make meaningful change. Since aging is inevitable, all should care about reframing aging and strengthening intergenerational relations that promote healthy aging.