Background The COVID-19 pandemic has triggered substantial changes to the healthcare context, including the rapid adoption of digital health to facilitate hospital-to-home transitions. This study aimed to: i) explore the experiences of hospital and community providers with delivering transitional care during the COVID-19 pandemic; ii) understand how rapid digitalization in healthcare has helped or hindered hospital-to-home transitions during the COVID-19 pandemic; and, iii) explore expectations of which elements of technology use may be sustained post-pandemic. Methods Using a pragmatic qualitative descriptive approach, remote interviews with healthcare providers involved in hospital-to-home transitions in Ontario, Canada, were conducted. Interviews were analyzed using a team-based rapid qualitative analysis approach to generate timely results. Visual summary maps displaying key concepts/ideas were created for each interview and revised based on input from multiple team members. Maps that displayed similar concepts were then combined to create a final map, forming the themes and subthemes. Results Sixteen healthcare providers participated, of which 11 worked in a hospital, and five worked in a community setting. COVID-19 was reported to have profoundly impacted healthcare providers, patients, and their caregivers and influenced the communication processes. There were several noted opportunities for technology to support transitions. Interpretation Several challenges with technology use were highlighted, which could impact post-pandemic sustainability. However, the perceived opportunities for technology in supporting transitions indicate the need to investigate the optimal role of technology in the transition workflow.