Privacy over the internet is a critical issue worldwide, as more and more of the world executes business and personal transactions over the internet. Tor is a network layer that allows for anonymous internet activity for its clients by routing through ‘onion routers’, and claims to be a completely secure and private system for its clients. In ‘Large Scale Simulation of Tor’ by Blott et. al., the security weaknesses of Tor are explored through the lens of the SSFNet simulator. For this project, we look to a more modern simulator called Shadow that hopes to more faithfully reflect the actual Tor topography, traffic patterns, and source code, in order to build a more accurate simulation. This project aimed to recreate a connection-starting attack over the Shadow simulator, which proved to be possible only on a smaller scale of the total Tor network due to computational limitations. Recreating such attacks in the Shadow environment is critical to building a secure Tor network, and for users to have faith in the product that they are utilizing.