This chapter introduces a qualitative study of user’s information-seeking tasks on Web-based media, by investigating user’s cognitive behaviors when they are searching for particular information on various kinds of Web sites. The experiment, which is a major part of the recently completed doctoral research at the Institute of Design-IIT, particularly studies cognitive factors including user goals and modes of searching in order to investigate if these factors significantly affect users’ information-seeking behaviors. The main objective is to identify the corresponding impact of these factors on their needs and behaviors in relation to Web site design. By taking a userbased qualitative approach, the author hopes that this study will open the door to a careful consideration of actual user needs and behaviors in relation to information-seeking tasks on Web-based media. The results may compliment the uses of existing quantitative studies by supplying a deeper user understanding and a new qualitative approach to analyze and improve the design of information on Web sites.