Relationships, built on trust, knowledge, regard, and loyalty, have been demonstrated to be fundamental to health care delivery. Strong relationships between patients and providers have been linked to more compassionate care delivery, and better patient experience and outcomes, and may be particularly important in primary care. The rapid adoption of digital technologies since the onset of COVID-19 has led health care systems to seriously consider a “digital-first” primary care delivery model. Questions remain regarding what impact this transformation will have on the therapeutic relationship. Using a rapid ethnographic approach this study explores how patient and provider understandings of therapeutic relationships and digital health technologies may influence relationship-building or maintenance between patients with complex care needs and their care providers. Three team-based primary care sites in Toronto, Ontario, Canada were included in the study. Across the three sites 9 patients with chronic health conditions, 1 caregiver, and 10 healthcare providers (including family physicians, family medicine residents, social workers, and nurse practitioners) participated. Interviews were conducted with all participants and 8 observations of virtual clinical encounters (phone and video visits) were conducted. Using social representation theory as a lens, analysis revealed that participants' constructions of therapeutic relationships and digital technologies were informed by their identities, experiences, and expectations. For participants to see technologies as enabling to the therapeutic relationship, there needed to be alignment between how participants viewed the role of technology in care and in their lives, and how they recognized (or constructed) a good therapeutic relationship. This exploratory work suggests the need to think about how both patients' and providers’ views of technology may determine whether digital technologies can be leveraged to meet patient needs while maintaining, or building, strong therapeutic relationships.