Young men have a critical role in preventing premature fatherhood, pregnancies, and sexually transmitted infections (STIs). However, grantees often share that it is difficult to recruit and engage young men in their projects—particularly within implementation sites that are not schools. Grantees aiming to engage male adolescents should make sure their programming is not only appealing to young men but that it challenges gender-exploitative activities that reinforce or take advantage of gender inequalities and stereotypes. This tool can be used to guide a discussion about engaging male adolescents in your APP projects. Use it to reflect on your organization’s readiness to recruit and engage male students and staff in community and juvenile justice settings. The tool is broken into three sections: sociocultural considerations, programmatic planning, and workforce development.