Abstract As more businesses begin to use encryption tech- nology, the security of data has enhanced tremendously over the years. However, it has also made it difficult to prevent data exfiltration. Conventional data loss prevention (DLP) tools often fail to scan encryption traffic, which makes them worse against advanced attacks. A different take on DLP architecture involves endpoint-based monitoring of data just before it gets encrypted. The different endpoint DLP architecture and their effective- ness in spotting and stopping encrypted data exfiltration is studied here. The study examines how these systems work, the methods they use and the problems they face in practice. The objective of this project is to provide an overview of the endpoint- based protection mechanisms in modern cybersecurity. Keywords Data Loss Prevention, Endpoint Security, Data Exfiltration, Encryption, Cybersecurity, Information Security