Abstract: Examples of the present disclosure describe systems and methods for contextual security training. In an example, a user may use a user device to perform a variety of actions within a computing environment. Occasionally, the user may encounter a computer issue, which may be identified by an issue detection processor. In some examples, it may be determined that the user should receive contextual training based on the identified issue so as to improve the likelihood that the user will avoid encountering or experiencing a similar issue in the future. Contextual training may be provided based on whether the user has a high incidence of encountering similar issues, among other criteria. If the criteria are satisfied, contextual training may be mandatory. In an example, contextual training may be adapted based on issue attributes to provide training tailored to a specific issue and/or issue type.