The year 2022 saw a significant increase in Microsoft vulnerabilities, reaching an all-time high in the past decade. With new vulnerabilities constantly emerging, there is an urgent need for proactive approaches to harden systems and protect them from potential cyber threats. This project aims to investigate the vulnerabilities of the Windows Operating System and explore the effectiveness of key security features such as BitLocker, Microsoft Defender, and Windows Firewall in addressing these threats. To achieve this, various security threats are simulated in controlled environments using coded examples, allowing for a thorough evaluation of the security solutions' effectiveness. Based on the results, this study will provide recommendations for mitigation strategies to enhance system security and strengthen the protection provided by Windows security features. By identifying potential weaknesses and areas of improvement in the Windows security infrastructure, this project will contribute to the development of more robust and resilient security solutions that can better safeguard systems against emerging cyber threats.