It’s dark because it uses encryption to hide the locations of everything on it from everything else. Users are anonymous and protected by a raft of privacy features baked directly into the Tor browser, which is the browser used to access it.
That leaves law enforcement not knowing where the websites are, who owns them, who uses them or who to arrest.
At least that’s the theory.
The reality is that while it’s hard to see in the dark, it’s not impossible to find things and over the last few years plenty of people who thought that Tor was a cloak of invisibility have come a cropper.
The people trying to hide on the Dark Web occasionally open doors that let the light come flooding in, bump in to the person chasing them or accidentally annoy organisations that happen to own very powerful torches.
Yup, there are in fact many ways to get busted on the Dark Web.
1. Being stupid or careless
Tor might be a very capable piece of technology built by very clever people but sophisticated tools are no match for operators who don’t know what they’re doing.
Using Tor, or setting up an anonymous .onion website, does not make you akin to an elite hacker.
On the Dark Web your website is a beacon of interest that needs to keep out both the bad guys and the good guys. If the bad guys break in they’ll walk off with your Bitcoin stash, and if the good guys break in they’ll use their access to figure out who and where you are.
Your site can stand out a mile on the Dark Web too.
A poorly secured website is vulnerable on any network but on the regular web it is at least a needle in a massive haystack of about 1 billion other sites. It takes some serious muscle to search the whole of that haystack but almost anyone can scan the entire Dark Web for sites with security flaws in just a few hours.
Even with your site locked down tight there are plenty of banana skins to slide on – all the anonymity in the world is worth nothing if you go and use a regular website like Reddit to tell everyone how terribly clever you are or you leave Exif data in your photos (the metadata that reveals when and where they were taken).
And then there’s the thorny business of actually selling real things to real people, with real addresses back in the well lit, real world.
In October 2014, undercover agents purchased a firearm from a vendor on the Dark Web marketplace Agora. All the encryption in the world couldn’t save US resident Michael Focia though. He’s facing up to 15 years in jail because he left his fingerprints on the gun.
2. Making the wrong friends
There aren’t many .onion sites on the Dark Web and when a new one appears the chances are that its arrival is of interest to many, many different law enforcement agencies around the globe.
Right now there are only about 7000 active Dark Web sites – that’s one for every five people employed by the FBI.
No wonder then that no matter if you’re a toxin-buying teen purchasing poison from a police officer, asking a cop posing as a hitman to bump off an ex-employee or your drug market is shuttered by a police sting within days of opening, it can feel like the Dark Web is stuffed to the gunwales with undercover fuzz.
And it isn’t just the real people that the criminals seeking refuge in the shadows have to worry about.
In 2013 1000 alleged paedophiles were identified by Netherlands charity Terre des Hommes thanks to ‘Sweetie’, their sophisticated CGI lure that looked and acted like a 10-year-old Filipina girl.
3. Making the wrong enemies
Be in no doubt that if you’re a criminal and you’ve just realised that the Dark Web might just the safest place to ply your illegal trade, then so have your mortal enemies.
The criminals might have given themselves a head start, but governments around the world have got some seriously smart people on the payroll (the onion routing technology that underpins the Dark Web was actually created by the US Navy).
The Dark Web isn’t just crawling with people who have the power to arrest and detain you, it’s also being indexed, sorted and catalogued by them using technologies like DARPA’s Memex search engine.
Memex was being used in secret for a year before it was revealed to the world but if the rumours are true then there are other, equally serious technologies being used out there that are still under wraps.
It seems that FBI hackers took down Silk Road, the Dark Web’s biggest and most notorious ‘Dark Market’, and they’ve been linked with attempts to get around Tor’s defences using malware.
Silk Road 2.0 suffered a similar fate when it was taken down along with dozens of other sites in a single day following a six month, 17-nation police operation called Operation Onymous.
Nobody’s come clean about how the police managed to pull off Operation Onymous. Europol are keeping tight-lipped, saying only that “This is something we want to keep for ourselves … because we want to do it again and again and again.”
Rumours persist that governments are infiltrating the Dark Web’s infrastructure by operating or compromising Tor entry guards and exit nodes. By controlling parts of the system, they can monitor and modify snippets of traffic.
With enough nodes they might even be able to perform sophisticated traffic correlation or network fingerprinting attacks.
The threat of exactly that kind of sophisticated operation is now being felt so keenly that it recently spooked the Dark Web’s biggest illegal marketplace into going offline.
Image of special forces courtesy of Shutterstock.com