The paper analyzes the issue of digital risks and digital security in the perception of generation Z and the reform generation, which is relevant in terms of different speeds of adaptation to digitalization processes among representatives of different cohorts. The authors identify, classify and describe these risks both from a theoretical position and in the context of perception by respondents. The paper describes the results of the study conducted by the technique of semi-structured interviews involving six focus groups with the participation of 37 respondents – representatives of the so-called reform generation and generation Z (digital generation). The purpose of the study is to identify the characteristics of the perception of digital risks and strategies for adapting to them among representatives of generation Z and the reform generation. As a common for all generations result, the authors propose a risk perception rating, which mainly emphasizes economic risks, risks related to the confidential information security, personal risks, and issues of surveillance on the Internet. The risk of losing control over personal and financial information on the Internet is considered the most dangerous one. Both generations refer technocratic strategies to the strategies for adapting to these risks. At the same time, the main conclusion concerns the degree of freedom in the implementation of communication on the Internet: generation Z is not afraid to communicate freely and implement its activities on the Internet and the reform generation representatives often prefer to limit their activity.