“Tor: From the Dark Web to the Future of Privacy” by Ben Collier

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Rating: 4/5 Stars.

A fascinating book about Tor (The Onion Routing), starting with its origins in the American military establishment, to its current day usage as a means to anonymously connect to sites over the internet or to covertly ‘leak’ information. The book doesn’t talk much about the technology used in Tor, but concentrates on the organisations and people who developed Tor, manage it and use it. They are the ones who will determine the future of Tor.

The book starts by looking at the Internet and the question of how to anonymously transfer data. In theory, anybody could monitor links at one or more internet service providers and determine who is sending data to whom. This was of concern to the US military, who wanted a way for overseas personnel to send data without other parties being aware of it. There were several solutions proposed, but the one they choose was ‘Onion Routing’. In Onion Routing, encrypted data was sent to an entry relay, which passes the data to another relay, which then sends the data to an exit relay and onwards to the destination. Each relay only knows how to pass on the data to the next relay.

If just one person was using Onion Routing, the route would be obvious. But the military envisioned Onion Routing being used by the public. Military traffic would then be mixed in with this traffic, making it much harder to determine which packets of data are being sent by whom. Entities monitoring only the entry or exit points would only know who is using it, but not why. Of course, a ‘global entity’ could monitor everything, but this can not considered possible at the time (the mid 1990s). This would, of course, change in later years.

Since the military needed the public to use Onion Routing, they had to recruit technologists to ‘sell the technology’ to their groups. This group of people would be the security hackers and ‘technology libertarians / anarchists’ of that period, who saw how internet technology was being monitored (or subverted) by the government, and had an idealised vision of the technology being ‘free’ from government intervention or censorship. From this strange grouping of people (those who want to control the internet and those who want it to be ‘free’), Tor was born.

As Tor usage grew, usability would become an issue. The creation of the Tor Browser would provide users with a ‘one click’ solution to use Tor, helping it to grow in popularity. This would lead to ‘The Dark Web’, a set of hidden (Tor) services for illegal activities like pornography or drugs. While headlines at the time might lead people to believe most of the Dark Web is Tor based, in reality such transactions are mostly done (protected by encryption) using the standard internet. What Tor did allow was anonymous transactions to be created, leading to a growth in the use of cryptocurrencies for anomymous payment, and for the dumping of information on sites like WikiLeaks.

Later on, another group of people would start to use Tor: the activist, agitating for action and using Tor as a way to hide their activities from organisations that want to stop them. Leaks at the time would also show some governments were trying to achive a ‘global view’ of the internet by gathering vast amounts of data from numerous providers, causing a change in Tor to counteract such measures.

Which brings us to the present. While Tor is used and does its job, it is still not very widely used, and associated with the Dark Web in the eyes of the public. Tor was initially funded by the military, but now looks to funding from various non-governmental groups and organised in a way to ensure no one person can exert undue influence on it.

In closing, the book argues that Tor is still looking for a ‘killer app’ that would bring about wider usage of Tor, and help the general public to secure privacy in their communications from governments that seem to want to accumulate more ways to observe when people are doing on the internet.

Book read from 2025/08/14 to 2025/08/20.