The rapid growth of the web has transformed our daily lives and the need for secure user authentication and authorization has become a crucial aspect of web-based services. JSON Web Tokens (JWT), based on RFC 7519, are widely used as a standard for user authentication and authorization. However, these tokens do not store information about the user’s behavior history. To address this issue, this paper presents a solution to enhance the trustworthiness of user authentication in web applications based on their behavior history. The solution considers factors such as the number of password attempts, IP address consistency, and user agent type and assigns a weight or percentage to each. These weights are summed up and stored in the user’s account, and updated after each transaction. The proposed approach was implemented using the .NET framework, C# programming language, and PostgreSQL database. The results show that the proposed solution effectively increases the level of trust in user authentication. The paper concludes by highlighting the strengths and limitations of the proposed solution.