Cybersecurity is becoming a need more than ever. Organizations need to protect their digital assets and are required to earn certifications to prove the compliance to the regulations and rules. For this, these assets must be assessed to ensure the target security posture and to get certified or pass an audit on yearly basis. This is a daunting and costly task as it often requires a third-party tester that tries to penetrate the system, under agreement. Breach and Attack Simulation is a new method that allows to do this penetration testing in-house, using some automation tools. Some of these tools can be using scripts of known attack vectors, and running them in sequence. This, however, does not cover unknown zero-day attacks. An intelligent way would be to try to account for potential attack that are unknown. We envision that using some Machine Learning techniques trained on some types of vulnerabilities can make this automation smarter.