Abstract: The dissertation explored conventionalization in content structure of two website types by addressing the following research questions: (1)  To what extent do websites of a particular type, originating in a single country and language, demonstrate similarity in their content structure: What kind of content can be consistently recognized across such websites? (2)  What expectations do users have as to the content structure of a particular section of websites of a particular type? (3) To what extent do users’ expectations of content structure agree with observed regularities in the content structure of a particular section of the sites of a particular type? (4) What impact (if any) does the mismatch between user expectations of and the observed regularities in the content structure have on user interaction with the site? The study was guided by the genre theoretical framework and also utilized methodology accumulated by the research on mental representations. The research agenda called for an exploratory study employing analysis of selected websites’ content structure and a user study. In answer to RQ #1, selected academic and corporate sites demonstrated features of emerging genres: conventional content structures, geared towards their target audiences, and type-dependent differences in form. The identified trends were translated into the prototype content structures. In answer to RQ #2, the study found that users possessed certain expectations of content organization of website sections, which they tended to rely on when interacting with the sites and recalling the interaction. These expectations were shown to be site type-dependent. In answer to RQ #3, comparison of expectations to the observed practices showed that typically observed trends were commonly expected by the users. Frequency-of-use and diversity of content structure were suggested as factors affecting development of expectations. In answer to RQ #4, the analysis of cases of match and mismatch between expectations and actual structures suggested that this match or mismatch can make the user-site interaction succeed of fail. The results also suggested that the negative effect may be amplified in case of better developed expectations.