Studies showed that obtaining personalized health information facilitates patient education and compliance. Older adults with various comorbidities and their caregivers could potentially benefit from obtaining personalized health information via a web-based patient portal. However, it is not clear whether this population, that could potentially most benefit from a patient portal, is likely to make use of this technology. The goal of this project was to assess feasibility of patient portal in older patients and their caregivers. Older adults with congestive heart failure or chronic obstructive pulmonary disease and their caregivers were introduced to a patient portal, given timed tasks to accomplish using the portal and then interviewed about the experience. The older patients appeared to require significantly more time on most tasks than caregivers and were more likely to need assistance. The content of the portal did not match health literacy level of this population and navigation of the portal appeared to be cumbersome for the most of the older patients. Despite multiple deficiencies in user experience, both older patients and caregivers believed that using such a system is important and may improve their self-care. Adequate training and support is required for older adults and their families who will use a patient portal. The usability and appropriate content presentation issues have to be addressed for successful use of patient portals by older adults and their caregivers.