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Adverse drug events (ADEs) impact the health and safety of older adults. ADEs may lead to unplanned medical visits that influence health and related costs. The purpose of this study was to explore ADEs reported by rural, community-dwelling older adults. Data were collected on 138 participants' demographics, physical and mental health, sleep, medications, and ADEs. One or more ADEs were reported by 48% of participants, including central nervous symptom disturbances (16%), dry mouth (12%), hoarseness, gastrointestinal irritation, and decreased libido (all 8%). Poor sleep and poor physical health were associated with higher reported ADEs (p < 0.05). Older adults (ages 79–99) and those with higher physical health were 60% less likely to report ADEs. Those with poorer sleep quality were 50% more likely to report ADEs. Viable strategies are needed to monitor and reduce ADEs in community-dwelling older adults who use multiple medications to manage poor health and poor sleep.