This report presents an investigation into the security of a VMware-based virtual machine system. It begins with the installation procedure of the VM image file, detailing the steps taken to set up the environment, including the use of Ubuntu and Kali Linux. The report then delves into an inspection of the security system, focusing on identifying vulnerabilities and potential threats. This includes an analysis of automatic security updates, system hardening techniques, the importance of strong passwords, SSH security and hardening, and the use of disk encryption. The investigation also covers account security and the various security measures that can be implemented to protect the system. The report concludes with a set of suggestions for enhancing the security of the system, providing a comprehensive overview of the security assessment and recommendations for improvement.