This one looks like a promising read:
Tor, one of the most important and misunderstood technologies of the digital age, is best known as the infrastructure underpinning the so-called Dark Web. But the real “dark web,” when it comes to Tor, is the hidden history brought to light in this book: where this complex and contested infrastructure came from, why it exists, and how it connects with global power in intricate and intimate ways. In Tor: From the Dark Web to the Future of Privacy,Ben Collier has written, in essence, a biography of Tor—a cultural and technological history of power, privacy, politics, and empire in the deepest reaches of the internet.
I’ve always been cautiously curious about the Tor project. I remember listening to a Tor talk at a PyCon Italy (or EuroPython?) conference, where the speaker insisted that Tor wasn’t meant for dark usages but as a means of liberation. Tor: From the Dark Web to the Future of Privacy might help frame the project from that perspective.
It’s packaged as a free PDF. It’s too bad it’s watermarked, so converting it to EPUB results in a mess.