With the birth of the modern web, arguably marked by the 1982 standardisation of the internet protocol suite, the problem of storing sensitive or illegal data looms large. Early solutions involve physical "data havens" – the informational analogues of tax havens – in the Caribbean that promise to host everything from gambling operations to illegal pornography. Late 1990s As the internet goes mainstream, falling storage costs coupled with advances in file compression set off an explosion of darknet activity, as users begin to share copyrighted materials. Soon, the internet's peer-to-peer data transmission gives birth to decentralised data hubs, some of which, such as so-called topsites – where most illegal music and movie files originate – are password-protected and known only to insiders. Others, such as Napster, operate in the open and facilitate millions of file transfers per day. March 2000 Software developer Ian Clarke releases Freenet, revolutionary software that offers anonymous passage into the darkest reaches of the web, where one can access everything from child pornography to instructions on how to build explosives. "Freenet is a near-perfect anarchy," Clarke tells The New York Times. "I have two words for companies [trying to halt free file-sharing]: Give up."

June 2000 Libertarian cyberpunks Ryan Lackey and Sean Hastings go into business on Sealand, a bizarre, nominally independent state located on a World War II-era sea fort off the British coast. The start-up, called HavenCo, envisions hosting restricted data (except spam, child porn and money-laundering activities) on high-tech nitrogen-encased servers hidden in the fort's legs. Despite generating considerable attention, HavenCo begins to bleed money almost immediately, and by 2002, Lackey and Hastings have jumped ship. September 20, 2002 Researchers at the US Naval Research Laboratory release an early version of Tor ("The Onion Router"), which conceals the location and IP address of users who download the software. Originally designed to protect the identity of American operatives and dissidents in repressive countries such as China, Tor also has another natural constituency: denizens of the darknet. January 2005

Wired magazine estimates the "media darknet distributes more than half a million movies every day." Propelled by booming bandwidth, the underground network explodes into wholesale copyright infringement, from Hollywood blockbusters to Microsoft Office. A study by IT research firm IDC estimates software piracy alone costs businesses $34 billion worldwide in 2005. January 3, 2009 A man calling himself Satoshi Nakamoto "mines" the first Bitcoin, a form of untraceable cryptocurrency. Unlike previous digital currencies that failed because there was nothing to prevent users from literally copying their money, Bitcoin makes use of an innovative public accounting ledger that prevents double spending. Unsurprisingly, the cryptocurrency is an instant hit in the darknet, its anonymity making it a perfect tool for money laundering and criminal activity. 2010 Cyber security and intelligence firm Procysive estimates the darknet is home to "more than 50,000 extremist websites and more than 300 terrorist forums." The illicit sale of pirated digital content, it reports, "serves as a source of financing for [terrorist] operations."

June 1, 2011 A Gawker-affiliated blog publishes an exposé on Silk Road, a hidden marketplace that "makes buying and selling illegal drugs as easy as buying used electronics." It's like Amazon.com for crystal meth and LSD, except only available to Tor users with Bitcoin accounts. Traffic to Silk Road surges, and the value of a Bitcoin jumps from around $US10 to more than $US30 within days. August 1, 2013 Irish authorities raid the Dublin apartment of Eric Eoin Marques, described by the FBI as "the largest facilitator of child porn on the planet." His arrest coincides with a mysterious shutdown of vast swaths of the darknet, allegedly as part of an FBI sting operation that exploited a breach in the web browser Firefox to identify Tor users. Users' identities are reportedly routed back to a server in Northern Virginia. August 4, 2013

The US government intercepts secret communications between al-Qaeda chief Ayman al-Zawahiri and Nasir al-Wuhayshi, the head of the Yemeni-based al-Qaeda in the Arabian Peninsula. The online confab leads to the shuttering of US embassies in 21 countries across the Muslim world. According to researchers at the Institute for National Security Studies in Israel, the high-level al-Qaeda talks "apparently took place in a part of the internet sometimes called deepnet, blacknet or darknet". October 1, 2013 The FBI shuts down Silk Road and arrests Ross William Ulbricht, known by his online moniker Dread Pirate Roberts, for allegedly masterminding the operation. The site did more than $US1.2 billion in sales between 2011 and 2013, according to an indictment filed in US federal court. October 4, 2013 The Guardian reports the NSA has repeatedly targeted people using Tor by exploiting vulnerabilities in other software on their computers. According to a 2007 top-secret internal presentation leaked by former NSA contractor Edward Snowden, the agency "will never be able to de-anonymise all Tor users all the time," but with manual analysis, it can "de-anonymise a very small fraction of Tor users".

October 2013 Technology news site The Verge reports online markets such as Black Market Reloaded and Deepbay, both of which openly advertise narcotics, are seeing a surge in traffic. "No doubt we will all regroup elsewhere," one Silk Road moderator wrote after the marketplace was shuttered. "I look forward to seeing all of you again ... still engaging in free trade without government interference into your personal affairs." In November, a new anonymous darknet marketplace called Silk Road 2.0 was back online, a little more than a month after the original was shut down. Foreign Policy