This study documented the provision of services and issues experienced by community organizations supporting older adults and caregivers in the province of Quebec during the coronavirus disease (COVID-19) pandemic, as well as promising strategies to adapt the provision of services in this context. A cross-sectional electronic survey using open- and closed-ended questions was conducted in July 2020. Almost three-quarters of the 307 respondents (71.4%) reported having maintained services at least partially throughout the lockdown, and the majority (85.3%) adapted their services. Among key challenges, participants reported difficulties identifying and supporting older adults at greater risk of vulnerability (54.8%), managing health risks for service users (60.2%), and recruiting volunteers (59.5%). Promising strategies included strategies to reach out to older adults and understand their needs (e.g., systematic phone calls) in addition to direct interventions supporting them (e.g., activities promoting social ties); implementing prevention and protection measures; accessing and using technologies; human resources management (e.g., recruiting new volunteers); finding financial support for their organization; developing intersectoral partnerships (e.g., multisectoral crisis cell); and promoting a positive view of older adults. The integration of multiple perspectives from different stakeholders may help identify strategies potentially transferable to other crises in order to meet older adults’ needs.