Healthcare Information Technology (HIT) continues to hold immense promise for reducing medical errors, collecting instant and vast data from across medical providers, increasing effi ciency, improving clinician and patient satisfaction, sharing data, guiding clinicians with up-to-date fi ndings, and facilitating teamwork within and across professions. Yet, almost everywhere clinicians fi nd this technology frustrating and falling short of its promised benefi ts. In this chapter I examine the reasons for this chasm between promises and reality. In doing so, I review the many benefi ts of healthcare Information Technology (IT), the origins of electronic health records in both academic and commercial settings, government policies intended to spur the economy and encourage implementation of healthcare IT, the forces infl uencing those policies, vendor contracts, in addition to the role of the Offi ce of the National Coordinator of Healthcare IT and of other offi ces in the Bush and Obama administrations. I also explore the barriers to establishing data standards, interoperability, full and transparent evaluations of EHRs and similar technologies, sharing of problematic EHR screen shots, and rapid remediation of healthcare IT-linked diffi culties. Healthcare IT, despite its problems, provides many and essential benefi ts, and will continue to improve. To that end, I offer suggestions for bringing the promise and reality closer together.