The dark web allows for anonymous browsing and publishing of content and is inherently cross-border by design. Law enforcement’s best tool to police anonymous dark web sites is a suite of technologies known as “network investigative techniques” (NITs), which essentially hack The Onion Router (Tor) hidden services (i.e., darknet sites) to deanonymize users. Using Operation Pacifier, the Federal Bureau of Investigation’s (FBI’s) 2015 investigation of the Playpen child abuse content darknet site, as a case study, this paper explores the implications of the use of NITs and both the Fourth and Sixth Amendments. We find that initial conflicts between the rules governing search and seizure and the search of machines using the dark web have been reconciled with changes to law and evolving legal precedent. The issues surrounding the due process remain more open.