Cloud computing has revolutionized the contemporary technology environment by providing dynamic, on-demand computing capabilities with greater organizational capacity to attain more scalability, cost savings, and business flexibility. The resulting accelerated cloud migration has also introduced new risks, including man-in-the-middle (MITM) attacks, which are a significant threat. These attacks take advantage of the channels between service providers and cloud consumers to enable unauthorized parties to capture, modify, or steal confidential information without detection. As more mission-critical data and services move into cloud environments, the confidentiality of data, integrity of data, and trustworthiness of data are more important than ever. This work analyzes the risk of MITM attacks in cloud computing and the need for tight security controls such as end-to-end encryption, multifactor authentication, and persistent threat monitoring to detect, resist, and prevent such invasions. Furthermore, through emulation of an attack scenario using CloudSim, this work demonstrates the real-world consequences of MITM vulnerability and evaluates countermeasure effectiveness against multilevel attack scenarios. The results underscore the urgency for cloud stakeholders to adopt adaptive layered security architectures to maintain the resilience and reliability of cloud services in the face of evolving cyber threats.