Data Loss is an everyday threat within all organizations. The leaking of confidential data ultimately results in a loss of revenue. A quarter of all Data Loss is widely attributed to the use of applications such as Voice, Email, Instant Messaging, Social Networks, Blogs, P2P and Videos. A common approach, adopted to prevent Data Loss is the use of sophisticated data detection algorithms and the deployment of systems to control applications, attempting to access the outside world. Many vendors currently offer data loss prevention products for no small amount of money. This thesis focuses on providing all the necessary information needed to fully comprehend the terms that wrap around data loss prevention and illustrating some of the most common mechanisms and techniques used by the available software. Also, two publicly available, free, data loss prevention software tools, MyDLP and OpenDLP, are presented and analyzed. In the third part of this project, a system architecture is presented, designed to combine the two previously mentioned software in a way such that they co-exist inside an information system, complementing each other, providing solid data loss prevention services.