The purpose of this study is to analyze the functional requirement of web-based portfolio supporting system and to investigate the relationship between learning portfolio and personal knowledge management. First, this study surveys the literature to explore the architecture of web-based portfolio supporting system. Then, a prototyping system that adopts the system architecture is implemented and finally this study evaluates the system by using the questionnaire and observing learners¡¦ operating conditions. A total of 69 subjects are from Kaohsiung Hospitality College. The main findings show that web-based portfolio supporting system meets learners¡¦ need mostly and has a positive effect on learners¡¦ learning process. Most learners are not familiar with portfolio assessment, and therefore teachers must make learners to understand what is portfolio assessment. A few learners organize and manage their personal learning portfolio according to their learning need. Furthermore, most learners are not used to sharing their files and knowledge. However, teachers can encourage learners to interact by promoting their sharing will. Finally, based on the research findings, this study proposes following suggestions for the follow-up research. 1. Portfolio assessment must be put into practice as soon as possible. 2. Improving teachers¡¦ participation to promote learners¡¦ will of interaction and sharing. 3. Adding teaching assistants to reduce learners¡¦ loading to establish learning portfolio.