Clinicians encounter many medical questions while providing outpatient medical care. A significant number of these questions can be answered using MEDLINE; however it has proven to be difficult to incorporate MEDLINE into routine clinical workflow and for clinicians to generate well constructed MEDLINE queries. This study however hypothesized that that well-constructed MEDLINE queries could be semi-automatically generated by an application named LitButton which was incorporated into the TeleWatch telemedicine system. The LitButton application was then prospectively evaluated in a pilot study by four nurse case managers (NCM) who monitored sixty-eight outpatients for three weeks. During this period the NCMs used the LitButton application sixteen times, and they subjectively reported in real-time that they obtained an answer in 56% of the cases, but that none of the successful information retrieval events resulted in a change in a patient's clinical management. The small number of LitButton events and lack of clinical impact was likely due to the fact that the LitButton function was designed to search MEDLINE for treatment related information; however the NCMs had limited medical decision making responsibilities. As a result there was a mismatch between the user's information needs and the system capabilities.