Medication errors are common among older adults, particularly among those who are at heightened risk due to transfer between care settings. Determining accurate medications for hospitalized patients is a complicated process. This paper presents findings from a small pilot study conducted to identify medication documentation problems at the point of hospital discharge among older adults and the problems encountered in developing new technological systems to address these problems. A prospective study was conducted within a managed care medical center that included patient and physician surveys and chart reviews. A review of 104 medical records revealed several problems in the documentation of patient medication including legibility, use of medical abbreviations and incomplete and missing entries. While patients overall were satisfied with medications communication efforts at discharge, physicians surveyed reported that these methods were inadequate in transmitting medication lists to primary care physicians, patients and other care providers. Patients reported taking more drugs than what were listed in the medical record. These findings led to the development, testing, and implementation of an electronic medication sheet. Despite the success in developing this new system, few physicians engaged in its use, with most preferring to continue with their standard discharge practices of written communication.