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I wonder why Tor Browser, Tails or Whonix are the most preferred ways of browsing Tor. What's wrong with manually doing a transparent proxy and routing all traffic over Tor through iptables? Why do it is a bad idea? Assuming, manually routing all traffic through Tor is done by a person who's familiar with Linux, networking, etc. then is doing it still a bad idea?

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  • Actually it is not as bad idea as you've told. But it may cause privacy issues. For example a script may send your real IP to a server using TOR. The server will see the TOR's exit node IP address while the script leaks your real IP. These kind of privacy issues are tried to be solved in Tor Browser, Tails or Whonix.
    – Mir Saman
    Commented May 16, 2019 at 6:40

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usually yes...

  • first the easiest one, because of error-proneness:
    i'm pretty sure the configuration (and code) of the mentioned projects is reviewed much more often than the configuration of someones single setup.

  • and its not just about how accessing the network, it is also about the clients and their configuration:
    --> the idea is to be not just anonymous (by hiding the IP), but also not traceable/pseudonymous (by vanishing in the masses of homogenous users)...
    hence blocking some IPs more or less than the usual Tor user, one not so wide spread addon installed and/or a pretty special resolution of your browser window and you are pretty easily trackable.

e.g. hardening the browser is a huge task! and also the devs of the mentioned projects are also working hard to make the fingerprint of their users look even.

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