Background: Microsoft Windows Security is a recently implemented safeguard for the Windows operating systems, including the latest versions of Windows10 and 11. However, there is a major shortcoming in this system to stop Advanced Persistent Threat (APT). These are government-financed groups that are funded to attack other government entities. Following the initial security breach, the hacked Windows device is used to access the rest of the network devices in order to transfer data to external storage (Exfiltration). Methods: In this work, we have tested the Microsoft Windows Security system using MITRE CALDERA and ATT&CK frameworks and explain how APT groups are able to bypass Windows Security. Results: In this study we used "54ndc47" agent through GoLang feature in MITRE CALDERA platform to test and bypass Microsoft Windows Security systems (MS Windows 10). Through it, we were able to bypass the Windows Security system and display entire files in the victim's device. Conclusions: In this paper, we have provided recommendations to Microsoft to improve their Windows Security tool through the use of Artificial intelligence (AI).