This project explores whether there is a reasonable expectation of privacy in a user's IP Address, specifically in scenarios where users are purposely employing anonymization measures that attempt to mask their IP Address. The project consists of a paper that argues for the reasonable expectation of privacy for the user's IP Address considering their attempts to gain privacy while traversing the internet. This paper discusses the differences in the top anonymization platforms and techniques. On the law side, the paper uses case law to justify the position of a reasonable expectation of privacy in an IP Address.