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Virtual Private Network (VPN) is a useful tool for accessing the web anonymously. It is steadily developing as an essential component of reducing the risks we are exposed to when going online. However, there is a risk factor which could destabilise the growth of the industry and users’ trust in the effectiveness of VPN services. This risk factor borders on the cybersecurity incidents that are threatening the competence of VPN providers. In this article, we will analyse the VPN’s cybersecurity threats and how technologies can help manage them.