The responsible and reliable use of web-based technologies is unquestionably crucial in the era of information abundance. Strategies aimed at mitigating false and misleading content online can be divided into structuralist and educational approaches. In this paper, we aim to demonstrate that most proponents of these strategies overlook the active role of users in web-based information and communication channels. They generally tend to view internet users as passive recipients of information who require external regulation and guidance to discern between reliable and unreliable online information in making well-informed judgments. What we aim to show is that responsible and meaningful engagement with information online encompasses much more than the existing proposals within demarcation approaches. It entails developing abilities that can be characterised as ‘third-order assessments’, which can help users not only to minimise the negative factors undermining the reliable use of information technology but also in ensuring reliable and responsible use of its communicative aspects. The paper concludes by offering suggestions on cultivating these skills and proposes their integration into school curricula.