Technologists are constantly working to improve clinical practice by developing new health information technology (Health IT) tools, yet may not always consider the context of how these tools may be used. Patient preferences can vary widely as a result of demographics, health conditions, physical limitations, and personal inclinations, with healthcare providers having to adapt clinical encounters to better suit patient needs. Health IT tools, too, need to be agile across different healthcare contexts, with each stakeholder's specific needs in mind. In this paper, we discuss the challenges and limitations associated with the design and automation of contextually sensitive devices in the healthcare environment. We target the various contexts in which health information is presented in patient-provider encounters, and discuss contextual constraints that may apply to the aforementioned situations. In addition, we present a number of suggestions for informational constraints and the design of informational tools in these settings so that patient and provider informational needs can be better met in clinical communication contexts.