Octogenarians living in the community are the fastest-growing demographic in Canada. Simultaneously, they have the highest prevalence of falls and nine times greater risk of injury due to a fall. To understand how to improve the safety of octogenarians’ aging-in-place, a systems approach is essential. Understanding how societal factors interact and affect the older adult can help care custodians identify and remove safety deficiencies that bring about falls. The purpose of this study was to identify system-wide factors contributing to falls in community-dwelling octogenarians. Eight falls were investigated using the systemic falls investigative method. Participants ranged in age from 83–90 years. Across-case analyses identified 247 contributing factors, grouped within four distinct themes: (a) everyday living has become risky; (b) supervision limitations; (c) health care system disconnects; and (d) poor fall risk identification and follow-up. This qualitative study provides systemic insights into how and why falls occur in community-dwelling octogenarians.