For many health centers and clinics, educating a diverse patient population about digital tracking tools to monitor blood pressure is a challenge. However, learning to adapt based on patient needs is vital to ensure both continuity of care and staff bandwidth. Asian Health Services (AHS) in Oakland, California, leverages health coaches and digital health advocates to support these evolving needs. They work closely with community members with varying levels of digital literacy as well as hypertension requiring different levels of management. For the care team, this allows them to move from a labor-intensive and sometimes inconsistent approach to hypertension, to the lighter-touch practice of remote blood pressure monitoring. In our conversation with George Lee, he shares Asian Health Services' multi-phase journey in patient education for remote care and where they've had to pivot along the way in order to better integrate IT into their existing operations.