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Although there is much practical interest in Web advertising as a component of marketing on the Internet, there is little theory or evidence about how it works in the context of Web content. This paper reports a laboratory experiment that examines the impact of advertising format (less or more intrusive), medium (print or Web) and Web content structure (linear or non-linear) on a broad range of measures of advertising effectiveness and evaluation of Web content. Several hypotheses based on human information processing considerations are developed and tested. The results show that advertising effectiveness is constant across advertising formats, media, and Web content structures. Evaluation of content was found to be unaffected by medium or Web content structure, but positive related to the presence of advertising, and negatively associated with the level of intrusiveness of advertising format.