This week we’re taking a radical shift away from industry and company discussions in favour of a less mainstream topic: the Dark Web. Last Thursday, in the culmination of a six-month investigation, authorities from both the EU and US took down 27 Dark Web websites, made 17 arrests and seized guns, drugs, gold, silver, cash, bitcoins, and a slew of other contraband. Some of the Internet’s most notorious criminals were among those detained, and some of the largest drug, weapons, and money laundering websites were taken offline. These seizures and arrests brought the Dark Web back into focus after almost of year a relative media dormancy. This got me curious about how it works and who is using it. Let’s start with a few simple definitions. The Dark Web is a subsection of the Deep Web, which includes all content that can’t be directly accessed through a search engine — it is estimated to be about 5,000 times larger than the surface web. The vast majority of this content is unavailable via search engines but not impossible to find — for example, Facebook posts typically don’t show up on Google searches — but pockets of it are intentionally hidden, and this is where the Dark Web begins. By far, the best known Darknet (a Dark Web network, of which there are many) is colloquially referred to as Onionland and is accessible only through a tool called Tor, or The Onion Router. Tor is an anonymity service; it allows users to browse the web incognito (true incognito, not the Chrome version) and, more importantly, hides websites and data setup using their services, making them only accessible for those using Tor. You can use Tor to browse both the surface web (as an anonymous user) and the Onion Network. When you surf the web through Tor, every sent request is given layers of encryption (like an onion) and then bounced around computers that have volunteered to be used as relay nodes. Each computer only knows the identity of the computers it connects to, so if a message is intercepted and decrypted (which itself is incredibly difficult), the third party still wouldn’t know who sent the request, or where it is going. As the Tor website explains, you can think of this as taking a really windy road, while simultaneously covering your tracks to get away from someone following you. While browsing anonymously is the primary Tor service, it is their hidden network (Onionland) that allows users to host websites without giving up their location or identity. Any website set up on Tor is given the top level domain name .onion and even if you have a direct URL you can’t access it unless you are connected to their network. So why is Tor a thing? It was originally created by the US Government as a way to anonymize their communications. Because Tor’s security becomes better the more people use it, they decided to open it to the public. The network grew quickly, and in the mid-2000s the government handed it over to a non-profit who overhauled and currently maintain it. The DarkNet and Tor are most frequently associated with illegal products and services and with good reason. The allure of anonymity combined with the incredible scale and convenience of the Internet make the web’s underground an attractive place for a wide range of criminals. Onionland is infested with websites selling narcotics, firearms, stolen items, hitmen for hire, credit card information, and a host of other illegal and black market goods. All transactions are done with bitcoins, which have the distinct advantage of being significantly harder to trace than traditional payment methods. On top of goods and services, networks like Onionland are a hub of information and communication. While much of the communication is just as nefarious as the goods and services mentioned above, these networks are also used as an open place to express ideas and opinions that may be unpopular or even dangerous when communicated without anonymity. Tor has become a vitally important tool in parts of the world where free speech is discouraged and dissidence punished. During the Arab Spring it helped opposition activists communicate and organize while avoiding detection and persecution. Closer to home, services such as <em>The New Yorker</em>’s Strongbox offer a secure way to whistleblow. People can use Tor to anonymously post to public forums on sensitive topics (such as rape or abuse), law enforcement can use it to investigate without leaving traces and websites containing sensitive information, such as Wikileaks or Indymedia, can use it to hide. Tor is primarily a privacy service, and its controversy stems from both the Darknet websites it harbours and its position on the online anonymity debate. There are a number of pertinent questions surrounding Tor, services like it, and their privacy for all approach. Should anonymity be a higher priority than the ability of law enforcement to do its job? Should Tor be available for everyone or should it censor its users? Should it be responsible for its dark side? Or more controversially, the vast grey area that makes up the majority of its traffic?