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 of cognitive factors including user goals and modes of searching. 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 user-based 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.