Despite heightened physical risks during the COVID-19 pandemic, older adults often reported better mental health than younger adults, suggesting significant resilience. We used longitudinal qualitative data to examine how difficulties and positive experiences contributed to this resilience. Weekly COVID-related difficulties and positive experiences were collected using internet surveys over eight weeks from 247 respondents aged 51–95 (M = 71.1, SD = 7.3). Nearly all identified at least one difficulty, and 76% had problems three or more times. Longitudinal thematic analysis (LTA) revealed that most were consistent in how they described they difficulties, including problems with everyday protective activities, psychological distress, social isolation, and cultural divide (disagreements over public health policy). Although 78% identified at least one positive, less than half (42%) did so at three or more time points. Positive experiences were more diverse across time, but some reported greater interpersonal connection by utilizing technology to increase social contacts. LTA revealed three stances towards positive experiences: active efforts, appreciative efforts (observation), and mixed efforts. While trait resilience was unrelated to the themes, the mixed approach towards positive experiences was associated with lower anxiety at the last assessment, emphasizing the importance of positive experiences during stress.