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Hypertext as a nonlinear, computer-based or digital text that is now used along with conventional, linear printed text and can be described as a relatively advanced text type. Moreover, hypertextuality is among the characteristics which differentiate online news from printed news. While digital writing has become more advanced with hypertextuality, its impact on users’ reading habits has gained importance as an underlying matter. In this context, the present research aims to provide an analysis of users’ experiences of reading digital news in the context of hypertextuality. This study begins by summarizing the studies on hypertextuality and news users. Following this, a case study is presented to analyze newspaper users’ reading habits in a digital setting to propose empirical evidence for the theoretical ideas of poststructuralist thinkers on hypertextuality. This part focuses on the hypertext reception practices of UMASS/Amherst Department of Communication undergraduate students through analysis of their news consumption patterns via an online survey. Based on the findings, this study contributes to the literature regarding journalism, technology, and digital writing by identifying the advantages and disadvantages of reading digital news. Although hypertextuality invites both writers and users to think in a nonlinear and cooperative way, it also leads to polarized opinions and newly emerging ethical issues.