Community services have played a significant role in supporting the psychosocial health and well-being of vulnerable populations during the SARS-CoV-2 (COVID-19) pandemic. To meet increased community needs, organisations were required to rapidly modify service provision, often using remote delivery systems. This in-depth study, undertaken early in the pandemic, explored staff and clients’ experiences of adapting to using telehealth to provide and access services in one regional social services agency. Semi-structured interviews from 15 staff and 11 clients from a regional not-for-profit agency in Western Australia were recorded and transcribed. Inductive coding, and thematic analysis identified eight subthemes, with experiences and perceptions of telehealth varying substantially among staff and client groups. Distinct benefits and challenges were associated with telehealth. Participants highlighted tensions and complexities and commented on the place of telehealth in the community service sector. Clients expressed the importance of relationships and communication. This study provides in-depth insights into the contextualised experiences of staff and clients during a time at which change was both enabled and necessary. The findings highlight the need for tailored service delivery; choice; client collaboration; ongoing staff training relating to telehealth; and guidelines specific to telehealth in the community service sector.