Passive network monitoring is very useful for the operation, maintenance, control and protection of communication networks, while in certain cases it provides the authorities with the means for law enforcement. Nevertheless, the flip side of monitoring activities is that they are natively surrounded by serious privacy implications and, therefore, they are subject to data protection legislation. Chapter 22 investigates the challenges related to privacy protection in passive network monitoring, based on a joint technical and regulatory analysis of the associated issues. After introducing the issue and its special characteristics, the chapter provides background knowledge regarding the corresponding legal and regulatory framework, as well as some related work. It then delves into the description of the legal and regulatory requirements that govern network monitoring systems, before providing an overview of a reference monitoring system, which has been designed with these requirements in mind.