The risk of social isolation among older persons received considerable attention during the COVID-19 pandemic, when measures such as staying at home and physical distancing were enforced. Public policy and programmatic interventions often consider expanding the use of digital technology, in particular internet-enabled devices that can help maintain social connections, as an approach to address social isolation. This study assesses in pre-COVID, there were common factors associated with the risk of social isolation, the use of devices that enable internet access, and the use of technology for social connections. The data analyzed comes from Transitions in Health, Employment, Social Engagement, and Intergenerational Transfers in Singapore Study, a national study of older Singapore citizens and permanent residents aged ≥62 years, collected in 2019. The study finds that older persons at higher ages, those with lower levels of education, in worse health, and financially worse off are at a higher risk of social isolation, as well as have lower proportions of regular use of devices and use of technology for social connections. Additionally, older persons at risk of social isolation are significantly less likely to use devices and technology for social connections. This implies that there are older person subgroups for whom digital technology innovations for maintaining social connections may not be effective. Concerted, patient, and repeated efforts by the government, family, and older persons themselves may help bridge the disparity in technology use among older persons.