Cybersecurity remains one of the most challenging subjects to develop accessible curricula for students in homeland security, emergency preparedness, and security-oriented degree programs. This article describes the development of a unique experiential learning opportunity that helps students overcome one of the most challenging learning objectives in such coursework: the conceptualization of sophisticated cyber operations. The hack-along is a simulated cyber operation exercise. Cyber experts guide students through multiple scenarios highlighting attacker and defender perspectives. Students ask detailed questions and discuss operational planning and decision-making strategies resulting in higher levels of student content engagement.