This paper addresses the role of consumer involvement in Web site evaluation. We investigate the factors that lead the consumer to be involved with one site more than another. Based on previous research, we use the psychological constructs, information-seeking tendency, and focused attention (Baumgartner & Steenkamp, 1996; Novak, Hoffman, & Yung, 2000) to define the “information profile” of a consumer; and sensation-seeking tendency and mood variability to define the “entertainment profile” of the consumer (Eliashberg & Sawhney, 1994). The information and entertainment factors are hypothesized to affect consumers’ utilitarian (need, value) and hedonic (interest, appeal) evaluations of involvement, respectively, and ultimately, the affect toward the Web site (Holbrook & Hirschman, 1982; Mano & Oliver, 1993; Zaichkowsky, 1985, 1994). We examine these evaluations for various Web sites, whose respective information andentertainment profiles are defined using elements such as informativeness, organization, and entertainment properties (Chen & Wells, 1999). The Web site properties are hypothesized to moderate the relationships between individuals’ profiles and their evaluations of involvement and affect. We conducted our study using three surveys: (1) collection of data for classifying Web sites on information and entertainment properties, (2) collection of data for measurement of involvement, and (3) collection of data for time-based measurement of involvement. Our results show that the consumer’s information and entertainment profiles significantly affect utilitarian and hedonic evaluations of involvement. We also find positive and significant relationships between the evaluations of involvement and affect toward the Web site. Further, we find that the Web site’s information-specific properties moderate the relationship between information profile of the consumer and his/her utilitarian evaluation of involvement. A set of results from representative time-based evaluations of involvement shows that the respective elements of evaluation of involvement show increase/decrease over time if there is a match/mismatch between the user and site properties.