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Is it practical to generate onion addresses and attempt to connect to them via the tor client or is there a better approach? How can one get an estimate of the number of services available?

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It is absolutely impractical to shoot in random directions hoping to hit something. There are roughly 10^24 possible addresses, and roughly 10^4 actual live onions. (If you can do 100/sec, you will have 1 hit per 30 billion years on average.)

More viable methods are to run a crawler, or possibly to run a HSDir and log descriptors.

If you just want to find onions, see this question: How do I find onion sites?

  • The answer states that many of the respective sites are not maintained. How are these sites maintained? Users simply send in their address of their hidden service? – Sebi Sep 27 '15 at 20:38
  • It differs. There are sites where people can submit onions, there are crawlers, there are wiki's. These are mostly 'just' someones hobby project. Sometimes hobby projects get abandoned or interrupted by real life. – Jobiwan Sep 27 '15 at 20:51
  • If one were to write a crawler would it take the brute force approach or are there more effective methods? Do you know of any such crawlers? – Sebi Sep 27 '15 at 20:59
  • A web crawler starts by reading a web page. It extracts the links from it and reads those, repeats this process. See en.wikipedia.org/wiki/Web_crawler I don't know of any that you can just download and run. – Jobiwan Sep 27 '15 at 21:04
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    It is the fingerprint of my relay: atlas.torproject.org/#details/… – Jobiwan Sep 27 '15 at 21:23

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