question: In recent years, the number of digital health tools with the potential to significantly improve delivery of healthcare services has grown tremendously. However, the use of these tools in large, complex health systems remains comparatively limited. The adoption and implementation of digital health tools at an enterprise level is a challenge; few strategies exist to help tools cross the chasm from clinical validation to integration within the workflows of a large health system. Many previously proposed frameworks for digital health implementation are difficult to operationalize in these dynamic organizations. In this piece, we put forth nine dimensions along which clinically validated digital health tools should be examined by health systems prior to adoption, and propose strategies for selecting digital health tools and planning for implementation in this setting. By evaluating prospective tools along these dimensions, health systems can evaluate which existing digital health solutions are worthy of adoption, ensure they have sufficient resources for deployment and long-term use, and devise a strategic plan for implementation.