Despite advancements in pedagogy and technology, students often yearn for more applied opportunities in information security education. Further, small businesses are likely to have inadequate information security postures due to limited budgets and expertise. To address both issues, an advanced course in ethical hacking was developed which allows students to perform security assessments for local businesses through red team engagements. This paper will allow academics to implement similar courses, improving security education for students and increasing opportunities for local businesses to receive affordable security assessments.