Older people in rural communities increasingly rely on the Internet to access essential health, finance, education, and other social services. However, their abilities to participate in the online service system are often undermined by a continuing ‘digital divide’. This divide may be exacerbated by the strategies of service providers who fail to recognise and respond to the needs of older rural clients. This paper is based on a case study in Clare, a small rural town in South Australia, and examines the experiences of older residents and local service providers in trying to engage online for digital service delivery. Drawing on two sets of in-depth interviews, the study uses a mix of thematic content analysis and social network analysis to identify the nature and extent of digital interactions between older people and service providers, and the enablers and challenges for online service engagement. Older participants demonstrated considerable interest in learning how to use the Internet for accessing particular services, with social support networks and third party facilitators being crucial enablers. Service providers’ ambitions to engage with older people online appeared more limited as a result of entrenched stereotypes of older non-users, a lack of internal digital skills, as well as organisational and funding constraints. The case study findings emphasise the importance of balancing the views of older people and service providers in the design of online engagement strategies. These insights are critical for improving online service delivery in rural communities affected by an increasing withdrawal of physical services.