This case describes how Mass General Brigham (MGB), the largest health system in Massachusetts, piloted an AI-powered ambient documentation program among a subset of clinicians. Renowned for its strong emphasis on research, innovation, and patient health outcomes, clinicians at MGB were also experiencing increasing rates of burnout and turnover, largely driven by the administrative burden of clinical documentation in the electronic health records (EHR). To address this issue, they introduced a pilot program to test ambient documentation tools which used natural language processing to transcribe and summarize physician-patient encounters, reducing time spent on documentation and allowing physicians to focus more on patient care. Early results showed promising reductions in burnout, intention to leave, and increased physician efficiency, but concerns about the technology remained. The technology could generate inaccurate notes with errors or hallucinations which made physicians resistant to learn and adopt it into their workflows. Leadership contemplated how to scale this technology responsibly without exacerbating existing challenges.