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<h4>Background</h4>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.<h4>Methods</h4>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.<h4>Results</h4>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.<h4>Interpretation</h4>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.