While healthcare information technology (HIT) offers extraordinary promise of clinical improvement and greater efficiencies, the realization of the promise must confront and overcome a number of challenges caused by incomplete and inappropriate software design. In this paper, we review several types of HIT design and workflow decisions that limit the value and utility of HIT in electronic health (medical) record (EHR/EMR), computerized physician order entry (CPOE), and electronic medication administration record (eMAR) systems. While remedies for problems of design or workflow may be either easy or difficult, , the industry creates additional barriers in the contractual relationships it creates between itself (HIT vendors) and the clinical facilities (hospitals, clinics, and physician offices) that purchase its systems. We suggest that the structure of those relationships may retard the progress and responsiveness of HIT.