In the wake of digitalization and recent technological innovation, news consumers have increasingly moved to online spaces to access news. As changes in consumer behavior appear even within these new contexts, several legacy news publishers that are often linked with high journalistic quality and trust are struggling to monetize on their content. In such struggles, an increasingly common sight over the last couple of years is the implementation of paywalls; digital boundaries that require consumers to pay before accessing content. This work applies a design thinking approach, utilizing a mixed-method methodology by interviews, surveys, workshops, prototyping, and testing, to explore the users’ experiences of navigating this landscape, while at the same time taking the perspective of legacy news publishers into account. The first part of the report entails the identification of a set of design challenges in this regard. The second part focuses on one such challenge—the onboarding experience of paying readership online—and explores possible solutions where the experience of the users and the business of legacy news publishers can merge. It argues that, while still inducing some degree of irritation in the users, a registration-first model with multiple choices to pay is likely to create new opportunities for news publishers as they seek to charge for content online, while at the same time being appealing to a larger audience. However, the role of the relationship between the individual reader and the content itself was identified as absolutely central in increasing the value perception of news online.