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In recent years, there has been a growing interest in so-called smart cities. These cities use technology to connect and enhance the lives of their citizens. Smart cities use many Internet of Things (loT) devices, such as sensors and video cameras, that are interconnected to provide constant feedback and up-to-date information on everything that is happening. Despite the benefits of these cities, they introduce a numerous new vulnerabilities as well. These smart cities are now susceptible to cyber-attacks that aim to “alter, disrupt, deceive, degrade, or destroy computer systems.” Through the use of an educational and research-based loT test-bed with multiple networking layers and heterogeneous devices connected to simultaneously support networking research, anomaly detection, and security principles, we can pinpoint some of these vulnerabilities. This work will contribute potential solutions to these vulnerabilities that can hopefully be replicated in smart cities around the world. Specifically, in the transportation section of our educational smart city several vulnerabilities in the signal lights, street lights, and the cities train network were discovered. To conduct this research two scenarios were developed. These consisted of inside the network security and network perimeter security. For the latter we were able to find extensive vulnerabilities that would allow an attacker to map the entire smart city sub-network. Solutions to this problem are outlined that utilize an Intrusion Detection System and Port Mirroring. However, while we were able to exploit the city's Programmable Logic Controller (PLC) once inside the network, it was found that due to dated Supervisory Control and Data Acquisition (SCADA) systems, there were almost no solutions to these exploits.