The article presents counterpoints cyber freedom and cybersecurity as determinants of shaping and functioning of the information society and the challenges that imply in the issues of the necessary regulations. In the discussion determinated by the topic, this article presents selected problems and considerations of selected aspects: the idea of freedom of the Network and Network users – awareness of their actions, motives and dangers related with using of the Web, its resources and the simultaneous functioning in a `real` reality – and virtual reality. In turn, the aspect of cybersecurity – in the mainstream discussion of this article – mainly refers to the results of tests conducted in people aged 18-26 years, in particular with regard to: the use of the network and its resources, anonymity and false sense of anonimity in network, knowledge of the rules and regulations about downloading and sharing files.