This course will focus on contested cyber environments and simulated adversarial activity with regards to assessment of information systems. We will explore defense and operation of various types of systems in a test network, being able to employ tools to administer, monitor, fight through, and perform forensic analysis on attacks. Students will understand how to setup an assessment process for systems and/or components, and how to effectively conduct a penetration test on a network and/or components. Students will be challenged to develop engineering solutions to stand up to threats and mitigate vulnerabilities. The goal will be understanding the various strengths and weakness in selecting a system configurations for the purposes of information security, and the steps in the penetration testing process, including intelligence, threat modeling, vulnerability analysis, exploitation, and reporting. The course will also include a practicum course project in which students will engage with industry in solving a real-world challenge.