Background and Objective: We investigated usage of and satisfaction with hearing aid devices in everyday life among older adults with hearing loss. Our research further advances the role of hearing contexts for hearing aid use and satisfaction. A central assumption was that hearing aid owners adapt the usage of the hearing aid devices to contextual demands of hearing depending on their personal resources. Methods: In a sample of 158 hearing aid owners aged 50-88 years, we examined proactive hearing aid use in everyday life and its association with the usage of, and satisfaction with, hearing aids. The study was administered online. Using an adapted version of the day-reconstruction method, participants reported hearing episodes during the preceding day. Hearing aid use was assessed via the proportion of waking time with hearing aids. Satisfaction with hearing aids was measured via the Satisfaction with Daily Amplification scale. Results: When using the hearing aids more often, and when reporting greater satisfaction, older adults indicated more diverse listening situations and experienced less variability in hearing quality with hearing aids. Conclusion: Our findings suggest that hearing aid owners may proactively use the hearing devices to master situation-specific demands and difficulties in hearing quality. Such findings underline that hearing aid use and satisfaction depend on the extent to which the devices help to manage everyday life successfully.