Most determinants of health originate from the “contexts” in which we live, which has remained outside the confines of the U.S. healthcare system. This issue has left providers unprepared to operate with an ample understanding of the challenges patients may face beyond their purview. The recent shift to value-based care and increasing prevalence of Electronic Health Record (EHR) systems provide opportunities to incorporate upstream contextual factors into care. We discuss that incorporating context into care is hindered by a chicken-and-egg dilemma – ie, lack of evidence on the utility of contextual data at the point of care, where contextual data are missing due to the lack of an informatics infrastructure. We argue that if we build the informatics infrastructure today, EHRs can give the tomorrow’s clinicians the tools and the data they need to transform the U.S. healthcare from episodic and reactive to preventive and proactive. We also discuss system design considerations to improve efficacy of the suggested informatics infrastructure, which include systematically prioritizing contextual data domains, developing interoperability standards, and ensuring that integration of contextual data does not disrupt clinicians’ workflow.