Population aging is a major concern worldwide. Active aging should be promoted by increasing the social participation of older adults and enabling them to remain involved in the community. Research has demonstrated the utility of digital resources for addressing the needs of older adults, which include networking, entertaining, and seeking health-related information. However, the digital divide among older adults (i.e., the “gray digital divide”) is increasingly being recognized as a social problem that may be related to poor well-being. To obtain updated local data on the prevalence of Internet access and usage and their relationship with perceived well-being, we conducted telephone interviews with a random sample of 1018 older adults in Hong Kong from January to July 2021 (This research has received funding support from the Interdisciplinary Research Matching Scheme, Hong Kong Baptist University). We found that only 76.5% of the participants had Internet access at home, a mobile phone data plan, or both, whereas 36.3% had never used Internet services and 18.2% had no digital devices. A younger age, male gender, higher education level, living with others, and higher self-perceived social class were associated with material access to digital devices and everyday use of Internet services. Participants who accessed the Internet every day had higher levels of life satisfaction and self-rated physical and mental health than those who rarely or never used the Internet. Hierarchical multiple regression analysis revealed that digital skills were significantly associated with self-rated mental health even when controlling for demographic variables (including age, gender, education level, and self-perceived social class). This study contributes to the limited body of literature on the relationship between Internet use, digital skills, and perceived well-being. Our findings highlight the importance of addressing the digital divide even in cities with high penetration of information and communication technology, such as Hong Kong. We also discuss our insights into the use of timely interventions for older adults to address the gray digital divide.