A system for automatic user skill-gap evaluation using a proxy server or a proxy application. The proxy server or application receives a user input from a user and analyzes the user input to determine whether the user input falls below an acceptable user skill threshold level. The user input consists of user activity within an application and the user activity is recorded in a user action log. To determine whether the user input falls below the acceptable user skill threshold level, the proxy server or application compares the user activity recorded in the user action log with user skill-gap behavior patterns created by a subject matter expert. In response to determining that the user activity recorded in the user action log falls below the acceptable user skill threshold level, the proxy server or application sends a specific training module to the user based on an identified user skill-gap.