The purpose of this study was to explore the feasibility of using a Web-based tool to provide tailored symptom management strategies for persons living with HIV (PLWH) and to estimate the effect size of the tool for future studies. Testing the components of the Web-based system was done by incorporating a repeated-measures design measuring the outcomes of symptom frequency and intensity, use of symptom management strategies, and engagement with health care providers. We recruited 42 PLWH; participants were enrolled in the study for 12 weeks and were asked to use the system and complete the questionnaires every 2 weeks. Our results showed that participants who used the strategies were more likely to have a decrease in symptom frequency and intensity. Findings from this feasibility study provide preliminary evidence for the use of a Web-based HIV symptom management tool with self-management strategies for individuals living with HIV infection.