Privacy and anonymity tools on electronic devices are increasingly commonplace. These tools provide challenges for digital investigators especially when trying to track down and uncover illegal activity such as the use of the “Darknet”, an illegal online service trading market which is hidden from the normal internet users and is often difficult to detect with digital forensic tools, especially if the user uses privacy and anonymity “protection” on their devices. However, digital forensic tools continue to evolve with the ability to detect internet usage, even those supposedly hidden by such privacy tools. These tools present privacy concerns to users. This work seeks to examine the extent that the Tor Browser Bundle protects a user’s privacy. Using a mobile digital forensics software by Paraben, E3:DS, we extract the mobile device’s data, a Samsung Galaxy Note 5 using the Android 6.0.1 operating system. While past research has claimed that using Tor protects user privacy, analysis of the data revealed we were able to extract the websites visited via Tor and extracted search terms from common shopping and social media websites. Implications from this research are three-fold: first, the study shows that E3:DS can reveal internet activity even while running applications that are supposed to provide privacy and anonymity; second, user’s activities are not fully protected when using the Tor Browsing Bundle to surf the internet; and, finally, there are weaknesses in the Tor Bundle that Tor developers need to address in their software to support their privacy claims.