Digital health technologies have the potential to improve health outcomes for older adults, especially for those recovering from stroke. However, there are challenges to developing these technologies, such as data absenteeism (where older adults' views are often underrepresented in research and development) and technology chauvinism (the belief that sophisticated technology alone is the panacea to addressing health problems), which hinder their effectiveness. In this study, we aimed to address these challenges by developing a wearable glove integrated with culturally relevant exergames to motivate older adults to exercise and, for those recovering from stroke, to adhere to rehabilitation. We conducted a moderated usability study with 19 older adults, of which 11 (58%) had a history of stroke. Our participants engaged in a 30-minute gameplay session with the wearable glove integrated with exergames, followed by a quantitative survey and an in-depth interview. We used descriptive analysis to compare responses to the System Usability Scale between those who had a history of stroke and those who did not. In addition, we analyzed the qualitative interviews using a bottom-up thematic analysis to identify key themes related to the motivations and barriers regarding the use of wearable gloves for rehabilitation and exercise. Our study generated several key insights. First, making the exergames exciting and challenging could improve exercise and rehabilitation motivation, but it could also have a boomerang effect, where participants may become demotivated if the games were very challenging. Second, the comfort and ease of use of the wearable gloves were important for older adults, regardless of their stroke history. Third, for older adults with a history of stroke, the functionality and purpose of the wearable glove were important in helping them with specific exercise movements. Our findings highlight the importance of providing contextual support for the effective use of digital technologies, particularly for older adults recovering from stroke. In addition to technology and usability factors, other contextual factors such as gamification and social support (from occupational therapists or caregivers) should be considered to provide a comprehensive approach to addressing health problems. To overcome data absenteeism and technology chauvinism, it is important to develop digital health technologies that are tailored to the needs of underserved communities. Our study provides valuable insights for the development of digital health technologies that can motivate older adults recovering from stroke to exercise and adhere to rehabilitation.